Dissolution of Healy Ranch, Inc.

2026 S.D. 15

Opinion

#30666-aff in pt, vacate in pt, & rem-JMK 2026 S.D. 15

IN THE SUPREME COURT OF THE STATE OF SOUTH DAKOTA

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IN THE MATTER OF THE DISSOLUTION OF HEALY RANCH, INC.

APPEAL FROM THE CIRCUIT COURT OF THE FIRST JUDICIAL CIRCUIT BRULE COUNTY, SOUTH DAKOTA

THE HONORABLE PATRICK T. SMITH Judge

BRET HEALY Chamberlain, South Dakota Pro Se appellant.

LEE SCHOENBECK JOE ERICKSON of Schoenbeck & Erickson, P.C. Watertown, South Dakota Attorneys for appellee Healy Ranch, Inc.

CONSIDERED ON BRIEFS FEBRUARY 18, 2025 OPINION FILED 03/04/26 #30666

KERN, Retired Justice

[¶1.] Healy Ranch, Inc. (HRI) filed a petition for court supervised

dissolution. Healy Ranch Partnership (HRP), through its managing and majority

partner, Bret Healy, moved to dismiss the petition, asserting that HRP owns a

majority of the capital stock in HRI, and that as such, a majority of HRI’s

shareholders did not approve the proposed dissolution. Soon after the motion to

dismiss was filed, the circuit court issued an order to show cause to Bret and his

attorney, Tucker Volesky, “as to why they have not violated SDCL 15-6-11(b) and

why they should not face sanctions for said alleged violations.” The order to show

cause alleged that the motion to dismiss was unsupported and contradicted by well-

established facts, namely, that: (1) Bret and/or HRP owned no more than a one-

third interest in HRI; (2) Bret swore falsely in the statement of certification of HRP

by stating that less than 50% of the outstanding shares of HRI supported

dissolution and that Volesky filed the certification, knowing it contained a false

statement; and (3) in support of the knowingly false claims, irrelevant and

unnecessary filings were made with the “sole intent to relitigate past lawsuits and

to harass and cause unnecessary delay or needless[ly] increase the cost of

litigation.”

[¶2.] The circuit court concluded Bret violated SDCL 15-6-11(b)(1) and

Volesky violated SDCL 15-6-11(b)(1)-(3). The court imposed a monetary sanction

against Bret in the amount of $240,000 and against Volesky in the amount of

$10,000. In addition to the monetary sanction, the circuit court indicated it was

“duty bound” to report Volesky’s conduct to the Disciplinary Board of the State Bar

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of South Dakota, and it ordered that Volesky comply with any directives the

Disciplinary Board should issue. Bret, now appearing pro se, appeals the circuit

court’s sanction.1 We affirm the circuit court’s determination that Bret engaged in

sanctionable conduct under SDCL 15-6-11(c), but we vacate the imposition of

monetary sanctions and remand for a hearing and reconsideration of the various

types of sanctions, and if a monetary sanction is imposed, a determination that

includes Bret’s ability to pay the monetary sanction.

Factual and Procedural Background

[¶3.] This latest appeal involving HRP and Bret began as a petition for court

supervised dissolution filed by HRI. However, the issues on appeal are wholly

unrelated to that petition, and instead relate to the circuit court’s sanctioning of

Bret based on his unrelenting quest to establish his ownership of HRI and/or the

Ranch, despite the circuit court’s conclusion that “the very issue [Bret] is litigating

has been determined contrary to his position, and frequently.” Accordingly, the

history of the parties and the other actions in which Bret has actually, or could

have, litigated these same issues is important to the Court’s review of the circuit

court’s sanctions.

History of the Ranch, HRP, and HRI

[¶4.] The Ranch is located in Brule County, South Dakota, and has been

owned or occupied by the Healy family since 1887. The Ranch was farmed by

Emmett and DeLonde Healy (Bret’s grandparents) until Emmett’s death in 1969.

1. Volesky did not appeal the monetary sanction imposed against him. The Court suspended Volesky’s license to practice law for a period of 90 days. Matter of Discipline of Volesky, 2025 S.D. 62, 28 N.W.3d 146.

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Prior to Emmett’s death, he created a partnership, giving ownership of the Ranch to

himself and Bret’s father, Robert. After Emmett’s death, DeLonde inherited

Emmett’s half of the partnership and Robert and DeLonde later created another

partnership (the 1972 partnership) with Robert and his wife, Mary Ann Osborne,

owning half and DeLonde owning the remaining half. Although the 1972

partnership agreement was never signed, a deed transferring Healy Ranch into the

partnership was recorded. After Robert died in 1985, Mary Ann (mother of Bret,

Barry, and Bryce) became the sole owner of Robert’s share.2

[¶5.] The following year, DeLonde, Bret, and Mary Ann created a third

Healy Ranch partnership (the 1986 partnership), granting Bret 25% and Mary 75%

ownership interest in the Ranch. DeLonde relinquished all control over the Ranch

and signed a general warranty deed in 1989 purporting to effectuate the agreement,

but neither the partnership agreement nor that deed were recorded.

[¶6.] In 1995, Mary Ann and DeLonde executed a warranty deed

transferring Healy Ranch from the terminated 1972 partnership to a corporation

exclusively owned by Mary Ann—HRI. HRI was incorporated in 1994 under South

Dakota law as a family farm corporation, consisting of approximately 1,700 acres of

2. At the time Robert died, he and Mary owned 75% of the partnership assets. The 1972 partnership agreement provided that in exchange for Robert’s services as the managing partner, DeLonde would vest 10% of her original capital contribution in Robert and Mary Ann for each of the first five years of the partnership, so that at the end of five years, Robert and Mary Ann would own 75% of the assets and DeLonde would own 25%.

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real property.3 At the time of incorporation, Mary Ann was the sole shareholder of

HRI. In 2000, Mary Ann sold her shares in HRI to her sons, Bret, Barry, and Bryce,

with each of them purchasing a one-third interest in HRI.

[¶7.] The ownership of HRI is challenged by Bret in his motion to dismiss

the petition for court supervised dissolution, where he claims, inter alia, that HRP

owns, at the very least, a majority of the stock in HRI, and that as a result, a

majority of the shares of HRI did not approve the petition for dissolution. The basis

for the circuit court’s sanctioning of Bret is that the ownership issue had been

decided against Bret on many occasions in prior actions in which the ownership and

control of the Ranch and HRI were at issue. We, therefore, summarize the prior

actions that the circuit court found to have involved ownership in some fashion.

The prior litigation

[¶8.] Bret’s barrage of claims involving, directly or indirectly, ownership of

HRI and the Ranch began in 2017, when he brought suit against his mother, Mary

Ann, his two brothers, Bryce and Barry, the family’s attorney, Steven Fox, HRP,

and HRI, claiming to own 50% of the Ranch “pursuant to his interests in [HRP and

HRI].” Healy v. Osborne, 2019 S.D. 56, ¶ 2, 934 N.W.2d 557, 559–60 (Healy I). In

that case, Bret asserted a number of tort and contract claims, including conversion,

fraud, conspiracy to commit fraud, breach of contract, breach of the implied

covenant of good faith and fair dealing, breach of fiduciary duties, and negligence.

3. The history of HRP and HRI is set forth more fully in Healy v. Osborne, 2019 S.D. 56, 934 N.W.2d 557 (Healy I), Healy Ranch P’ship v. Mines, 2022 S.D. 44, 978 N.W.2d 768 (Mines), and Healy Ranch, Inc. v. Healy, 2022 S.D. 43, 978 N.W.2d 786 (Healy II), as well as in subsequent cases in both this Court and the federal district court.

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Id. ¶ 11, 934 N.W.2d at 561. He also alleged unjust enrichment and requested that

the court pierce the corporate veil of HRI. Id.

[¶9.] The circuit court in that case dismissed the action, concluding Bret’s

claims were untimely. On appeal, Bret argued that the statute of limitations was

tolled due to defendants’ alleged fraud and that he was in a fiduciary relationship

with Mary Ann. Id. ¶ 25, 934 N.W.2d at 564 & n.6. Bret claimed that “Mary [Ann]

retained 20.89% of the corporation because she only conveyed 162,000 shares to her

sons pursuant to the 2000 contract for deed rather than the entire 299,348 shares

she began with.” Id. He alleged “he remain[ed] in a fiduciary relationship with her

because she maintain[ed] her status as one of the majority shareholders in a closely-

held corporation.” Id. However, during the summary judgment proceedings in the

circuit court, Bret admitted that he and his brothers each owned a one-third

interest in HRI.

[¶10.] Additionally, Bret maintained in Healy I that “his interest in the

[1986] partnership remained intact,” but the Court held “his actions did not reflect

this belief.” Id. ¶ 29, 934 N.W.2d at 565. In support, the Court stated:

Until shortly before he initiated this action, Bret ignored the partnership following the creation of Healy Ranch, Inc. He did not record the 1986 partnership agreement or the 1989 deed. The partnership did not file a partnership return or pay property taxes after 1995, and Bret represented that his shares of Healy Ranch, Inc. stock were his only asset on an individual financial statement in November 2001. Bret’s comment to Barry in a June 2016 e-mail is also telling. In that correspondence, Bret acknowledged: “I owned 25% of the place–mom insisted on 1/3 to everyone–so yes I did put all my chips back in for 8% . . . .”

Id. The Court noted that “Bret also alleged that Mary [Ann], with the assistance of

[Attorney] Fox, fraudulently transferred two lots—RH-1 and RH-2—out of the

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partnership property in 1988 and 1992. He alleged that the 1986 partnership

owned both RH-1 and RH-2, and that Mary [Ann] signed two warranty deeds in her

individual capacity and as executrix of the Robert E. Healy Estate to unlawfully

transfer the lots to other individuals.”4 Id. ¶ 6 n.1, 934 N.W.2d at 560 n.1.

[¶11.] On appeal, this Court noted that HRP was formed in 1986 and with

that formation, Bret received an interest in the Ranch. The Ranch was later

transferred to HRI, which at that time, was “exclusively owned by Mary [Ann].” Id.

¶ 6. However, “[i]n 2000, Bret, Bryce, and Barry each purchased a one-third

interest in [HRI] from Mary [Ann] pursuant to contract for deed.” Id. ¶ 7. We

further noted that Bret represented on several occasions that HRI was the sole

owner of the Ranch. However, we did not determine ownership of the Ranch in

Healy I, stating, “We decline to address Bret’s claim of ownership because the

threshold issue in this case centers on the timeliness of Bret’s claims for conversion,

breach of contract, fraud, conspiracy to commit fraud, unjust enrichment, breach of

fiduciary duties, and negligence.” Id. ¶ 21, 934 N.W.2d at 563.

[¶12.] The Court ultimately concluded that Bret’s claims were barred by the

applicable statutes of limitations. The Court also affirmed the circuit court’s

finding that Bret’s lawsuit was frivolous and malicious, noting that “Bret filed the

lawsuit for the purpose of preventing the sale of the property, not because he

believed his partnership interest remained enforceable.” Id. ¶ 37, 934 N.W.2d at

567. Accordingly, the Court affirmed the circuit court’s award of attorney fees, sales

4. This allegation is the subject of a later lawsuit brought by Bret, which is discussed below.

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tax, and costs in the total amount of $83,295.42 ($32,606.54 to Mary Ann;

$38,283.88 to Bryce, Barry, and HRI; and $12,405 to Fox), and additionally,

awarded appellate attorney fees and costs—$7,500 to Bryce, Barry, and HRI, $7,500

to Mary Ann, and $3,450 to Fox. Id. ¶¶ 16, 38, 934 N.W.2d at 562, 567.

[¶13.] In Healy Ranch Partnership v. Mines, 2022 S.D. 44, 978 N.W.2d 768

(Mines), HRP, through Bret, filed a quiet title action to a parcel of the Ranch

commonly known as Lot RH-2 or RH-2. The action named the individuals in

possession of RH-2 (Larry and Sheila Mines, together the Mineses), as well as the

previous possessors and another member of HRP, as defendants. The Mineses filed

a counterclaim, asserting title through adverse possession. Id. ¶ 1.

[¶14.] The record in that case revealed that in 1990, HRP entered into

negotiations to sell RH-2 to Raymond Sharping, and Mary Ann executed a warranty

deed on August 1, 1992, conveying RH-2 to Raymond and Evelyn Sharping.5 Id. at

¶ 10, 978 N.W.2d at 773. Upon Evelyn’s and then Raymond’s death, RH-2 passed to

his son, Randolph Sharping, via Raymond’s will. Randolph Sharping executed and

recorded a warranty deed for RH-2 in favor of the Mineses on June 21, 2012, and

Bryce, acting on behalf of HRI, executed and recorded a quitclaim deed to RH-2 in

favor of Randolph on June 26, 2012.

[¶15.] In 1995, Mary Ann and DeLonde executed a warranty deed purporting

to transfer the Ranch (excepting RH-2) from HRP to HRI. Bret alleged, however,

that HRP remained the owner of all 1,700 acres of the Ranch, claiming Mary Ann

5. The full history of the ownership of RH-2 is set forth in Mines, 2022 S.D. 44, ¶¶ 1–14, 978 N.W.2d at 772–74.

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was not authorized to transfer HRP’s real estate to HRI without his consent.

According to Bret, Mary Ann converted her 75% interest in HRP into HRI, which

became a partner with Bret in HRP. Bret claimed he and his brothers purchased

only their mother’s 75% interest and left intact Bret’s 25% interest under the 1986

partnership agreement. However, after HRI’s creation, it appears the Ranch’s

lenders dealt only with HRI and, most often, with Bret, who is listed on loan

documents as HRI’s president.

[¶16.] Relevant to the competing claims of the ownership of RH-2, we noted

in Mines that in the years following the Sharpings’ possession of RH-2, Bret

executed several documents that excluded RH-2 from the Ranch’s real estate

holdings. Further, Bret stated he was aware that the Sharpings began farming RH-

2 in 1990, although he has made varying claims regarding the circumstances under

which they did so. Nevertheless, Bret claimed in Mines that RH-2 was not

transferred at all, maintaining that “Mary Ann’s lack of authority to transfer RH-2

means that any act to convey the property was ‘null and void’ and, as a

consequence, HRP still retains ownership.” Mines, 2022 S.D. 44, ¶¶ 20–21, 978

N.W.2d at 775. This was a different claim than what Bret asserted with respect to

this property in Healy I.

[¶17.] In our opinion addressing the appeal from the circuit court’s rulings

against Bret in Mines, we noted Bret’s inconsistent theories:

Before addressing the merits of the Mineses’ adverse possession claim, however, we must first determine whether Bret, in the name of HRP, may claim the Sharpings’ use of RH-2 was permissive, given his position regarding RH-2 in Healy v. Osborne. As indicated above, Bret’s arguments regarding RH-2

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in Healy v. Osborne and his assertions regarding the same tract of land made in this action are perceptibly different.

In Healy v. Osborne, Bret alleged that Mary Ann and the family’s attorney had actually transferred RH-2, though fraudulently and without authority. 2019 S.D. 56, ¶ 6 n.1, 934 N.W.2d at 560 n.1. In fact, Bret claimed during his deposition in the Healy v. Osborne litigation that the transfer of RH-2 “has caused the loss of land” because “it was transferred to Raymond Sharping.”

Bret’s theory in this quiet title action brought in the name of HRP is different, however. He now claims that RH-2 was not transferred. Instead, Bret asserts that Mary Ann’s lack of authority to transfer RH-2 rendered any act to convey the property “null and void,” leaving HRP as the owner. With this predicate, Bret develops his factual theory that Raymond Sharping and his successors have, from 1990 to the present, all occupied RH-2 with HRP’s permission.

Mines, 2022 S.D. 44, ¶¶ 50–52, 978 N.W.2d at 782. We stated that Bret “taking

inconsistent positions in this way implicates the doctrine of judicial estoppel.” Id.

¶ 53.

[¶18.] After analyzing the varying claims under our judicial estoppel

principles, we concluded: “Under the circumstance presented here, the application

of judicial estoppel is appropriate. Bret may not, in the name of HRP, re-fashion his

claim regarding RH-2 into a quiet title action that contemplates the land was never

transferred and, instead, has been permissively used for the past thirty years by

others who have farmed it and paid the taxes.” Id. ¶ 60, 978 N.W.2d at 784.

Ultimately, we concluded that the circuit court properly held that the Mineses

“established title to RH-2 by adversely possessing the property under the terms of

SDCL 15-3-15.” Id. ¶ 69, 978 N.W.2d at 786. Our decision in Healy I did not,

therefore, address the substance of Bret’s ownership claim.

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[¶19.] While Healy I was pending on appeal, Bret filed a notice of claim,

asserting HRP held an interest in the Ranch. Healy Ranch, Inc. v. Healy, 2022 S.D.

43, ¶ 1, 978 N.W.2d 786, 790 (Healy II). Bret’s notice of claim specifically listed the

parcels that constitute the Ranch—the same property that was at the heart of

Bret’s principal claims in Healy I. Id. ¶ 10, 978 N.W.2d at 792. HRI then brought a

quiet title action against Bret and HRP, seeking to establish “marketable title”

under the South Dakota Marketable Title Act (SDMTA) and to void Bret’s notice of

claim. HRI alleged that Bret had not filed his notice of claim within the governing

twenty-two-year statutory period, and it requested costs and attorney fees, claiming

Bret filed the notice of claim for the sole purpose of slandering HRI’s title. Id. ¶ 11.

[¶20.] The circuit court granted HRI’s motion for summary judgment,

“concluding that Bret’s notice of claim was not timely under the SDMTA.” The

court, however, denied HRI’s request for costs and attorney fees, concluding “there

has not been a showing to the [c]ourt’s satisfaction that this was done for the

purpose of slandering title[.]” Id. ¶ 15, 978 N.W.2d at 792–93 (alterations in

original). The court rejected HRI’s claim that the previous award of attorney fees in

Healy I conclusively established that Bret’s claim that HRP owned the Ranch was

frivolous and malicious. Id.

[¶21.] On appeal, this Court disagreed with the circuit court’s conclusion

regarding timeliness. However, we nevertheless concluded that res judicata barred

Bret’s “counterclaim seeking to quiet title in HRP.” Id. ¶ 39, 978 N.W.2d at 798.

We explained:

Bret’s quiet title counterclaim in this case is an overt effort to litigate the same cause of action that he litigated in [Healy I].

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Although the specific legal theories advanced in the two cases are different, of course, Bret is again addressing the same wrong he identified in [Healy I]—the alleged wrongful conduct by members of his family to vest HRI with ownership of the Ranch. The underlying facts are the same, as is Bret’s principal argument that HRI does not truly own the Ranch.

Id. ¶ 49, 978 N.W.2d at 800 (citation modified). We, therefore, concluded:

Bret was aware of each and every fact necessary to have brought his quiet title action in 2017. Instead, he elected to pursue different claims and remedies whose lack of success should have signaled the end of the dispute. He cannot now extend the life of those claims against members of his family by repurposing them in an effort to litigate the same wrong premised upon the same facts. Though his notice of claim may have been timely filed, the cause of action is precluded, and the notice should be voided on this basis.

Id. ¶ 59, 978 N.W.2d at 802–03. Accordingly, the Court again did not reach the

substance of Bret’s ownership claim in Healy II.

[¶22.] Even before Healy II was decided, Bret also filed a complaint in federal

district court against Mary Ann, Bryce, and Fox, under the Racketeer Influenced

and Corrupt Organizations Act (RICO), alleging mail fraud, bank fraud, and

conspiracy to engage in a pattern of racketeering. Healy v. Fox, 572 F. Supp. 3d

730, 734–35 (D.S.D. 2021) (Fox), aff’d, 46 F.4th 739 (8th Cir. 2022).6 As

summarized by the federal district court, Bret alleged:

On August 8, 2017, he received HRI tax documents during discovery in a lawsuit against the Defendants in state court revealing that HRI shares issued in 1994 to Osborne, which were subsequently transferred to Bret in 2000, were void because she failed to provide proper consideration when she established the corporation. Bret contends, “the transfer of the

6. The RICO action was commenced on February 21, 2021, and Bret filed an amended complaint in that action one day after oral argument before this Court in Healy II.

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land did not and could not represent consideration for the shares of the Corporation because the property interest in the land never belonged to Osborne personally. At the time of formation of HRI, the land belonged to the partnership-not to Osborne.” Therefore, according to Bret, because an asset of a partnership belongs to the partnership and not an individual, the exchange of the partnership’s interest in real property for the issuance of HRI stock to Osborne was invalid and thus the shares issued were void.

Id. (citation modified). The district court dismissed Bret’s suit based on res

judicata, noting first that “Bret claimed injury in the state court action from the

1995 transfer from the partnership to HRI because it deprived him of his interest

held by the partnership. In the amended complaint, Bret claims injury from the

1995 transfer from the partnership to HRI because it was part of an illegitimate

stock issuance that ultimately provided the vehicle for the RICO conspiracy.

Therefore, the ‘underlying facts’ which give rise to each cause of action are the

same.” Id. at 743.

[¶23.] On appeal, the Eighth Circuit Court of Appeals affirmed, noting that,

“in 1995, Osborne conveyed all of the partnership’s real-property interest in the

ranch to HRI,” including Bret’s share. The court further noted:

In 2000, Osborne sold one third of her shares of HRI to Bret and one third to each of his two brothers, Bryce Healy and Barry Healy. From 1999 to 2017, Bryce served as secretary and treasurer of HRI with responsibility for all of the financial recordkeeping. Bret received yearly Schedule K-1 tax forms, which showed that he owned one third of the stock of HRI.

Fox, 46 F.4th at 742 (emphasis added). The Eighth Circuit concluded, “Bret is

again addressing the same wrong he identified in [Healy I]—the alleged wrongful

conduct by members of his family to vest HRI with ownership of the Ranch.” Id. at

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744 (citation omitted). The resolution of that action in district court and on appeal

was based on res judicata.

[¶24.] Bret and HRP brought a second federal court action against this Court,

HRI, Mary Ann, Barry, Bryce, Fox, and the Mineses, alleging a due process

violation by this Court, fraud, misrepresentation, and other misconduct. Healy v.

Sup. Ct. of S.D., No. 23-CV-04118, 2023 WL 8653851, at *1 (D.S.D. Dec. 14, 2023)

(Healy III), reconsideration denied, No. 23-CV-04118, 2024 WL 2150336 (D.S.D.

Apr. 11, 2024). In an amended complaint filed March 24, 2021, Bret also named the

South Dakota Supreme Court justices and circuit court judge, Jon Sogn, in their

official and individual capacities, claiming a deprivation of his civil rights under 42

U.S.C. § 1983. Id.

[¶25.] Important to the Court’s determination here, in Healy III, the district

court found that Bret sought to have the district court “declare Plaintiff Bret Healy

to own two-thirds of the shares of HRI, contrary to what was adjudicated in state

court; to reduce Barry and Bryce Healy’s ownership of HRI to one-sixth each,

contrary to what was adjudicated in state court; and for other and further relief.” Id.

at *2 (emphasis added). The district court described Bret’s action as “an attempt to

have this Court reverse Healy I, Healy II, and Fox and declare Bret Healy the

winner, notwithstanding the Supreme Court of South Dakota decisions and the

prior federal court litigation affording res judicata effect to those decisions.” Id.

The district court dismissed the action, noting in part, “Res judicata on several

levels now bars the extraordinary relief [Bret] seek[s] from this Court—reversal or

vacating of the Eighth Circuit final decision from the prior litigation and reversal

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and vacating of three final decisions of the Supreme Court of South Dakota.” Id. at

*12.

[¶26.] In addition, the district court imposed sanctions under Rule 11 of the

Federal Rules of Civil Procedure, concluding in part, “the arguments made about

. . . how res judicata does not bar the state-law claims were not warranted by

existing law or a good faith, nonfrivolous argument for some modification or

extension of existing law. The history of litigation combined with the absence of

merit of the claims justify an award of attorney fees to the non-state defendants as

sanctions under Fed. R. Civ. P. 11(b)(1) and (2).” Id. The district court awarded

attorney fees to Mary Ann in the amount of $16,487.51; to HRI, Barry, Bryce, and

the Mineses in the amount of $14,463.63; and to Fox in the amount of $18,320.56.

See Healy III, 2024 WL 2150336, at *2.7 On appeal from the district court’s order

dismissing his action and imposing sanctions against him, the Eighth Circuit Court

of Appeals affirmed without opinion. Healy v. Sup. Ct. of S.D., No. 24-1996, 2025

WL 999468, at *1 (8th Cir. Apr. 3, 2025) (per curiam).8

7. The district court’s decision on sanctions came after the circuit court in this case imposed sanctions against Bret in the amount of $240,000, and after notice of appeal in this case was filed. Further, as a result of the circuit court’s sanctions in this case, Bret also instituted another action in federal district court, naming the clerk of court and circuit court judge Smith as defendants in Healy v. Miller, 4:24-cv-4053-RAL, Doc. 1, Doc 1-1. See Healy v. Sup. Ct. of S.D., No. 23-CV-04118, 2024 WL 2150336, at *1 (D.S.D. Apr. 11, 2024), aff’d, Healy v. Miller, No. 24-2897, 2025 WL 1833809, at *1 (8th Cir. July 3, 2025) (per curiam).

8. By order dated May 9, 2025, the Eighth Circuit Court of Appeals denied Bret’s petition for rehearing and for rehearing en banc. The United States Supreme Court denied Bret’s petition for writ of certiorari. Healy v. Sup. Ct. of S.D., No. 25-276, 2025 WL 3131828, at *1 (U.S. Nov. 10, 2025).

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The present case

[¶27.] The underlying case from which this appeal arose began with a

petition for court supervised dissolution of HRI, which stated that the shareholders

of HRI were brothers, Bryce Healy, Barry Healy, and Bret Healy, who each owned

1/3 of the total shares of the corporation. The petition alleged that HRI’s board of

directors adopted a plan of liquidation and dissolution and that a “majority of

outstanding shares of the common stock voted in favor of dissolution and adoption

of a plan.”

[¶28.] HRP, through Bret, and his legal counsel Volesky, filed a motion to

dismiss, asserting that HRP “owns, at least, a majority of the capital stock” in HRI

and that the “capital stock of [HRI] originates solely from the land transferred to it

by [HRP] as is shown by the capital structure on [HRI’s] tax returns.” HRP alleged

that it opposed the plan of liquidation and dissolution and that a majority of shares

of HRI “entitled to vote did not approve the proposal for voluntary dissolution.”

HRP filed a brief in support of its motion to dismiss, in which it argued that when

HRP transferred real property to HRI in 1995, the warranty deed transferring the

property stated “for the record that [HRP] was owner of at least a majority (in fact

all) of the capital stock of [HRI]” and that HRI’s “capital stock originates solely from

the real property transferred via Warranty Deed.” HRP also argued that the Ranch

is the property of HRP not HRI, claiming that Mary Ann did not have the authority

to transfer the “Partnership’s property”—the Ranch—without Bret’s consent. HRP

maintained that “all the capital contributed to [HRI] was contributed by [HRP].

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Indeed, [HRP] paid for the capital stock of [HRI] when record title to the

Partnership’s real property was transferred via Warranty Deed.”

[¶29.] Along with the motion to dismiss, Bret filed a certification as the

“managing, majority partner” of HRP, and a “substitute motion” that he claimed

was “proposed and supported by the shareholders holding a majority of the

outstanding shares of [HRI’s] common, paid-up, capital stock, at a meeting of the

shareholders held November 15, 2023.” Bret signed the certification as managing

partner of HRP.

[¶30.] Prior to the circuit court’s consideration of the merits of the petition

and motion to dismiss, the circuit court, on its own initiative, issued an order to

show cause, directing both Bret and Volesky to establish that they did not violate

SDCL 15-6-11(b) and should not face sanctions for such conduct. In support of the

order to show cause, the circuit court “alleged that said motion [to dismiss] is wholly

unsupported by law, unsupported and indeed contradicted by well-established facts

and numerous litigation, litigation that Tucker Volesky, as counsel for Bret Healy

and [HRP], is clearly aware of the fact that his clients Bret Healy and Healy Ranch

Partnership collectively own no more than a one third interest in [HRI], and that in

fact Bret Healy, Bryce Healy and Barry Healy each own 1/3 of all outstanding

shares of [HRI], and that therefore 2/3 of said shares, those owned by Bryce and

Barry Healy, voted to authorize dissolution.” The order to show cause stated that

Bret’s filings were “put forth with the sole intent to relitigate past lawsuits and to

harass and cause unnecessary delay or needless increase in the cost of litigation.”

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[¶31.] In response to the order to show cause, HRP/Bret took issue with the

various courts’ determinations regarding the ownership of HRI and claimed the

“facts from the previous litigation cannot be said to be well-established.” Bret also

noted that HRI had not moved for sanctions.

[¶32.] A hearing was held on Bret’s motion to dismiss and the order to show

cause on January 23, 2024. Bret testified at the hearing and his testimony was

largely consistent with his written response to the order to show cause. The circuit

court denied the motion to dismiss but took the question of Bret’s and Volesky’s

violation of SDCL 15-6-11 and possible sanctions under advisement.

[¶33.] In a detailed, 35-page memorandum decision dated March 18, 2024,

the circuit court determined both Bret and Volesky violated SDCL 15-6-11(b). In

doing so, the circuit court provided an overview of the lawsuits in which Bret was

involved, often represented by Volesky. The court also set forth the previous

sanctions and attorney fees that were imposed against Bret in many of these cases.

Based on the previous courts’ determinations in those cases, the court found that in

filing the motion to dismiss the petition for supervised dissolution, “it cannot be said

that Bret Healy was merely putting forth an unsuccessful theory or making a good

faith effort to modify existing law. Here the very issue he is litigating has been

determined contrary to his position, and frequently.” Accordingly, the circuit court

concluded:

It is clear and the finding of this [c]ourt that Mr. Healy is motivated to bring this action not by any belief in a supported legal claim, as those have all been turned away at the courthouse steps, but rather a clear and continuing effort to harass or cause unnecessary delay or needlessly increase the cost of litigation.

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The circuit court’s imposition of sanctions was based on its finding that the sole

basis for Bret’s challenge to the dissolution of HRI was his claim “that he has

greater ownership of [HRI], despite prior rulings by many courts that have heard

these issues.” The court imposed sanctions because it concluded that Bret’s

contention that HRP, and not Bryce and Barry, owned a majority of the stock of

HRI has been decided many times previously.

[¶34.] The circuit court imposed a monetary sanction of $240,000 against

Bret. In support of that amount, the court noted that although in previous cases

Bret was ordered to pay attorney fees totaling over $120,000, he was undeterred,

and concluded “[p]ast sanctions have had no effect on Bret.” As such, it was “the

intent of the [c]ourt to impress upon Mr. Healy that his actions have consequences

and should not continue, and [it is] the finding of this [c]ourt that the doubling of

his past sanctions will do so.”

[¶35.] Bret appeals the circuit court’s imposition of sanctions, raising several

issues9 that we restate as follows:

1. Whether Bret, as a represented party, is subject to sanctions under SDCL 15-6-11.

2. Whether the circuit court abused its discretion in imposing a monetary sanction against Bret.

9. Bret raises additional issues for the first time in his reply brief. “[I]t is well settled that a party may not raise an issue for the first time in the reply brief when the opposing party on appeal can no longer address it.” State v. Washington, 2024 S.D. 64, ¶ 44 n.4, 13 N.W.3d 492, 505 n.4 (citations omitted). As discussed below, we exercise our discretion to address one of these issues raised for the first time in his reply brief.

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Standard of Review

[¶36.] In Smizer v. Drey, the Court clarified the standard of review for

appeals pursuant to SDCL 15-6-11(a) through 15-6-11(d). 2016 S.D. 3, 873 N.W.2d

697. We noted that SDCL 15-6-11(e) requires this Court to consider these appeals

“without any presumption of the correctness of the trial court’s findings of fact and

conclusions of law,” but observed that our case law directs us to review such appeals

for an abuse of discretion. Id. ¶ 10, 873 N.W.2d at 701.

[¶37.] We then considered the United States Supreme Court’s treatment of

this issue in Cooter & Gell v. Hartmarx Corp., 496 U.S. 384, 403–04 (1990), where

the “Supreme Court specifically examined the issue of an appropriate standard of

review when a court imposes Rule 11 sanctions.” Smizer, 2016 S.D. 3, ¶ 11, 873

N.W.2d at 701. And, although we acknowledged “that the federal rule does not

contain language similar to SDCL 15-6-11(e)—that this Court is not to presume ‘the

correctness of the trial court’s findings of fact and conclusions of law’”—we found

the reasoning in Cooter & Gell “helpful because there is no decisive distinction

between the policy considerations implicated by our rule and the federal rule.” Id.

We also noted that “nothing in SDCL 15-6-11(e) imposes a specific standard of

review or mandates that this Court reweigh the evidence and reconsider the facts

already considered and weighed by the circuit court.” Id.

[¶38.] We further explained:

[T]he decision to impose Rule 11 sanctions under SDCL 15-6- 11(b) involves multiple factual and legal considerations. The circuit court must examine factual questions related to the attorney or unrepresented party’s representations to the court. SDCL 15-6-11(b). Legal issues are implicated when the court considers whether “[t]he claims, defenses, and other legal

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contentions therein are warranted by existing law or by a nonfrivolous argument for the extension, modification, or reversal of existing law or the establishment of new law[.]” SDCL 15-6-11(b)(2). And if the circuit court determines a violation occurred, it may exercise its discretion and “impose an appropriate sanction upon the attorneys, law firms, or parties that have violated § 15-6-11(b) or are responsible for the violation.” SDCL 15-6-11(c).

2016 S.D. 3, ¶ 12, 873 N.W.2d at 702 (second and third alterations in original).

[¶39.] The Court thus held that based on those considerations and the

language of SDCL 15-6-11, “we continue to adhere to our abuse of discretion

standard of review.” Id. ¶ 14. “An abuse of discretion is a discretion exercised to an

end or purpose not justified by, and clearly against, reason and evidence.” Id.

(citation omitted). “An abuse of discretion also occurs when the court bases ‘its

ruling on an erroneous view of the law or on a clearly erroneous assessment of the

evidence.’” Id. (citation omitted).

Analysis and Decision

1. Whether Bret, as a represented party, is subject to sanctions under SDCL 15-6-11.

[¶40.] Bret first argues he is not a sanctionable party, claiming Rule 11

restricts its reach to an attorney or unrepresented party, and he is neither. Bret

contends that he “was not initially even a party to the action.” While Bret did not

initiate the action, he signed a certification on behalf of HRP, asserting that HRP

owned the majority of HRI’s stock, and as the alleged majority owner, HRP

submitted a substitute motion opposing the dissolution and a motion to dismiss. As

a shareholder of HRI, Bret was personally served with the petition for supervised

dissolution.

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[¶41.] SDCL 15-6-11(b) and its federal counterpart, Fed. R. Civ. P. 11(b),

provide generally, that “those who submit pleadings, written motions, and other

papers to the district court, whether attorneys or unrepresented parties, must sign

those documents to signify that various certifications are being made.” 5A Fed.

Prac. & Proc. Civ. § 1331 (4th ed.). SDCL 15-6-11(b) states:

By presenting to the court (whether by signing, filing, submitting, or later advocating) a pleading, written motion, or other paper, an attorney or unrepresented party is certifying that to the best of the person’s knowledge, information, and belief, formed after an inquiry reasonable under the circumstances:

(1) It is not being presented for any improper purpose, such as to harass or to cause unnecessary delay or needless increase in the cost of litigation;

(2) The claims, defenses, and other legal contentions therein are warranted by existing law or by a nonfrivolous argument for the extension, modification, or reversal of existing law or the establishment of new law;

(3) The allegations and other factual contentions have evidentiary support or, if specifically so identified, are likely to have evidentiary support after a reasonable opportunity for further investigation or discovery; and

(4) The denials of factual contentions are warranted on the evidence or, if specifically so identified, are reasonably based on a lack of information or belief.

The text of Rule 11(b) provides that a signature by an attorney and unrepresented

party on a pleading or other document filed with the court makes four certifications,

including that any claim or defense is legally supportable.

[¶42.] However, subsection (c) of Rule 11 applies more broadly by permitting

a court to “impose an appropriate sanction upon the attorneys, law firms, or parties”

who have violated Rule 11(b)’s certification standards or who “are responsible for

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the violation.” (Emphasis added.) In other words, a party represented by counsel

may be subject to sanctions even if they have not signed the pleadings. But, Rule

11(c)(2) explicitly prohibits a monetary sanction against a represented party that is

based only on a violation of Rule 11(b)(2), relating to the certification that the

claims “are warranted by existing law or by a nonfrivolous argument for the

extension, modification, or reversal of existing law or the establishment of new law.”

SDCL 15-6-11(b)(2). As such, monetary sanctions are permitted against a

represented party for all other violations of Rule 11(b)(2). Indeed, courts have

permissibly imposed sanctions against represented parties for violations of Rule 11

that are not based upon a finding of frivolity. See, e.g., Kountze ex rel. Hitchcock

Found. v. Gaines, 536 F.3d 813, 819 (8th Cir. 2008) (affirming sanctions against a

party and his attorney where the district court determined that where the prior

action was dismissed with prejudice, naming a party “in the current action must

have been for an improper purpose”); Buster v. Greisen, 104 F.3d 1186, 1190 (9th

Cir. 1997), as amended on denial of reh’g (Mar. 26, 1997) (holding the district court

did not abuse its discretion in concluding that Buster’s action “was brought to

harass the Trustees,” and therefore, affirming sanctions against plaintiff and his

attorney) (citation omitted).

[¶43.] The circuit court’s memorandum decision discusses both that Bret’s

claims were asserted for an improper purpose and were frivolous:

In this case, it cannot be said that Bret Healy was merely putting forth an unsuccessful theory or making a good faith effort to modify existing law. Here the very issue he is litigating has been determined contrary to his position, and frequently. Objectively and on its face this action is frivolous defined. No rational argument exists to support it, no basis to argue for

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change has any chance of success, and no reasonable person should expect a favorable ruling.

The court, in a footnote, also found “that the basis of [Bret’s] challenge to

dissolution is frivolous, and intended only to delay and harass.” The impetus for the

circuit court’s sanctions was the fact that Bret claimed greater ownership of HRI

“despite prior rulings by many courts that have heard these issues.” However, the

circuit court’s findings, conclusions, and decision as a whole reflect that the

monetary sanction against Bret was based on the improper purpose of his actions.

To be sure, the circuit court discussed both that the claims asserted were frivolous

and that they were advanced for an improper purpose. But the court’s discussion

related not only to Bret, but also to his attorney Volesky, who was sanctioned for

violating three subsections of SDCL 15-6-11(b)—those relating to improper purpose,

frivolous arguments, and lack of evidentiary support. In contrast, the circuit court

concluded that Bret only violated one subsection—SDCL 15-6-11(b)(1)—relating

solely to improper purpose. The court explained, “It is clear and the finding of this

[c]ourt [is] that Mr. Healy was motivated to bring this action not by any belief in a

supported legal claim, as those have all been turned away at the courthouse steps[,]

but rather a clear and continuing effort to harass or cause unnecessary delay or

needlessly increase the cost of litigation.” (Emphasis added.)

[¶44.] Although the circuit court concluded that Bret’s claims were both

frivolous and asserted for an improper purpose, the court’s decision is clear that the

legal basis for its sanction against Bret was expressly limited to the finding of

improper purpose, as it directed in its order, “that Bret Healy be sanctioned in the

amount of $240,000 for violating SDCL 15-6-11(b)(1).” (Emphasis added.) The

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court’s findings of fact and conclusions of law also expressly conclude that Bret

violated only the subsection relating to improper purpose—“Bret violated SDCL 15-

6-11(b)(1)” and “Tucker Volesky violated SDCL 15-6-11(b)(1)-(3).”10

[¶45.] The dissent questions the ability to sanction Bret, stating Bret “was

not responsible for the legal arguments in this case; his lawyer, Volesky, was.” But

the history of Bret’s seemingly ceaseless litigation does not support this. Although

different attorneys were involved in several of the actions, the common denominator

is the active involvement of Bret in each of these actions. The dissent also

attributes Bret’s improper purpose to the frivolous arguments, stating that the

findings of improper purpose were “founded upon” the frivolous arguments by

Volesky, making them “effectively one and the same.” But the record supports the

circuit court’s conclusion that his frivolous claims were grounded on the improper

purposes identified by the court as Bret’s “clear and continuing effort to harass or

cause unnecessary delay or needlessly increase the cost of litigation.” The record

contains evidence that Bret and Volesky both violated Rule 11 and both should bear

responsibility. The circuit court’s decision to hold Bret responsible for his own

violation of SDCL 15-6-11(b) was not an abuse of discretion.

[¶46.] In short, while a court cannot impose monetary sanctions against a

represented party for a violation of Rule 11(b)(2), that was not the basis for the

10. We also note that Bret’s brief addresses the circuit court’s finding that his “motion to dismiss was presented for an improper purpose.” Likewise, HRI’s appellate brief discusses whether the circuit court erred in sanctioning Bret for “presenting papers before the court for an improper purpose” and arguing the circuit court’s “sanctions against Bret Healy were for violations of SDCL 15-6-11(b)(1), and thus do not run afoul of the limitation for a represented party contained in SDCL 15-6-11(c)(2)(A).”

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circuit court’s sanction against Bret here. As such, the circuit court did not err in

concluding that Bret was subject to monetary sanctions under SDCL 15-6-11(b)(1).

2. Whether the circuit court abused its discretion in imposing a monetary sanction against Bret.

[¶47.] Bret maintains that the circuit court’s sanction was erroneous,

claiming (1) he did not violate SDCL 15-6-11(b), (2) that his reliance on the advice of

counsel absolves him of responsibility, and (3) that the amount of sanctions—

$240,000—was excessive.

a. Whether the circuit court erred in determining Bret violated SDCL 15-6-11(b)(1).

[¶48.] Bret challenged the petition for dissolution of HRI based on his claim

that HRP owns, at least, a majority of the capital stock in HRI. The circuit court

found that Bret’s ownership claim had been previously (and frequently) determined

contrary to his position. The court also determined that Bret’s opposition to the

corporate dissolution was not motivated by any belief in a supportable legal claim,

but rather by a clear and continuing effort to harass or cause unnecessary delay or

needlessly increase the cost of litigation, in violation of SDCL 15-6-11(b)(1).

[¶49.] Bret first asserts the circuit court erred in concluding he violated Rule

11 because of its “complete misunderstanding of legal precedent which had

discussed – but not determined – the ownership of HRI. Judge Smith erroneously

claims the history of litigation proves that Bret’s continued claims of ownership are

false. The truth is that ownership of Healy Ranch has never been substantively

resolved.” In support of his assertion, Bret summarizes four of the lawsuits brought

by him or HRP.

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[¶50.] Beginning with Healy I, Bret claims the Court “did not determine

ownership of anything.” It is true that in affirming dismissal of Bret’s claims in

Healy I based on the applicable statutes of limitations, this Court did not determine

ownership of the Ranch. Healy I, 2019 S.D. 56, ¶ 21, 934 N.W.2d at 563 (“We

decline to address Bret’s claim of ownership[.]”). Bret then maintains that the

Court also did not decide ownership in Healy II, where we stated:

[W]e agree with Bret’s assertion that our decision in [Healy I] cannot be used to invoke issue preclusion in this case. The question decided in [Healy I] was whether Bret’s claims against his family and former attorney were time-barred. As indicated above, we did not determine the question at issue in this quiet title action, which relates to ownership of the Ranch.

Healy II, 2022 S.D. 43, ¶ 46, 978 N.W.2d at 799–800.

[¶51.] However, Bret ignores our later discussion in Healy II, where we

explained:

In our view, Bret’s quiet title counterclaim in this case is an overt effort to litigate the same cause of action that he litigated in [Healy I]. Although the specific legal theories advanced in the two cases are different, of course, Bret is again addressing the same wrong he identified in [Healy I]—the alleged wrongful conduct by members of his family to vest HRI with ownership of the Ranch. The underlying facts are the same, as is Bret’s principal argument that HRI does not truly own the Ranch.

Id. ¶ 49 (footnote omitted). After addressing each of the claims Bret made in the

prior actions, we held that Bret’s notice of claim was precluded, stating:

Here, Bret was aware of each and every fact necessary to have brought his quiet title action in 2017. Instead, he elected to pursue different claims and remedies whose lack of success should have signaled the end of the dispute. He cannot now extend the life of those claims against members of his family by repurposing them in an effort to litigate the same wrong premised upon the same facts. Though his notice of claim may

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have been timely filed, the cause of action is precluded, and the notice should be voided on this basis.

Id. ¶ 59, 978 N.W.2d at 802–03.

[¶52.] In regard to our decision in Mines, Bret claims we “held that the

[c]ircuit [c]ourt incorrectly read Healy I by utilizing certain factual findings

regarding ownership of the Ranch.” What Bret ignores from the Mines decision,

which is pertinent to our consideration of sanctions, is that we exposed the

inconsistencies in Bret’s theories, noting that in Healy I, Bret acknowledged RH-2

was transferred, but in Mines, he claimed that portion of the property was not

transferred, nor could it have been because he claimed Mary Ann lacked the

authority to do so. See Mines, 2022 S.D. 44, ¶¶ 50–52, 978 N.W.2d at 782.

[¶53.] Bret also cites to the federal district court’s opinion in Healy v.

Supreme Court of South Dakota, where the district court noted:

The court in Healy I specifically “decline[d] to address Bret’s claim of ownership” and instead “center[ed] on the timeliness of Bret’s claims.” Healy I, 934 N.W.2d at 563. The court found Bret’s contract and torts claims untimely and barred by the statutes of limitations; in so deciding, the Healy I court effectively prevented Bret Healy from challenging that each of Bret, Barry, and Bryce owned one-third of HRI, indirectly confirming the ownership status quo. In Healy II, a quiet title action, Plaintiffs attempted to argue HRP owned the Healy ranch, but the Supreme Court of South Dakota determined the claim was barred under res judicata. In Mines, HRP, controlled by Bret, argued that it, and not HRI, owned certain land and filed an action to quiet title to property, but the court decided against HRP and determined the Mineses retained title. Lastly, in Fox, this Court determined Plaintiff Bret Healy’s action under 18 U.S.C. § 1964(c) of the Racketeer Influenced and Corrupt Organizations Act was barred by res judicata and ruled for the defendants, which the Eighth Circuit affirmed on the same grounds.

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2023 WL 8653851, at *1 n.1 (alterations in original) (emphasis added). Bret claims

that the federal district court did not “cite any paragraph or any prior decision, or

any parts of the record from previous cases, [sic] for this declaration[,] which begs

the question as to what and when such status quo came into effect.” Bret then

surmises that the district court’s “declaration, and Judge Smith’s reliance thereon,

constitutes impermissible, vague fact finding.”

[¶54.] Bret’s assertions are patently wrong. When addressing the

defendants’ motion to dismiss based on res judicata, the federal district court

analyzed the prior cases, explaining:

Res judicata plainly bars the claims pleaded here because the state-law claims—Claims 2, 3, and 4—arise out of the same nucleus of facts where “the wrong sought to be redressed is the same” as in the prior state court case. In Healy I, Healy II, and the prior federal litigation, like in this case, “the wrong sought to be redressed” is Plaintiff Bret Healy’s assertion to greater ownership in HRI and its assets, or in the case of Mines, HRP’s claim to HRI assets. Plaintiffs attempt to argue the wrongs sought to be redressed in this case relate to “frauds, misrepresentations, misconduct and fraud upon the courts” occurring in the litigation of the prior cases, . . . but Plaintiffs’ Prayer for relief requests this Court “[d]eclar[e] Bret Healy owner of two-thirds of all the outstanding shares of HRI capital stock,” . . . thereby undermining this argument. Indeed, Plaintiffs’ Prayer in the Amended Complaint seeks to have this Court vacate all prior state and federal decisions and declare “Plaintiffs’ future rights and remedies unaffected by” those decisions. . . . The first element of res judicata is met because the “fraud, misrepresentation and misconduct” claims arise out of the same nucleus of facts.

Id. at *10. Contrary to Bret’s claim, the district court did cite to the previous

cases—both to the pleadings and to the decisions—and the district court did not

engage in “vague fact finding” as Bret asserts in his brief.

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[¶55.] Considering these prior cases in their entirety, the circuit court in this

case determined that Bret’s claims were barred by principles of res judicata and/or

collateral estoppel. Although this was the primary basis for the circuit court’s

ultimate conclusion that Bret’s claims were brought for an improper purpose, Bret

has not addressed these principles or the circuit court’s findings in regard to them.

Such failure waives the issue on appeal. First Nat. Bank in Sioux Falls v. Drier,

1998 S.D. 1, ¶ 20, 574 N.W.2d 597, 601 (plaintiff’s failure to address the issue in its

brief waived the issue on appeal). Nevertheless, we exercise our discretion to

address these important issues because whether Bret’s claims were precluded by res

judicata and/or collateral estoppel is foundational to the propriety of the circuit

[¶56.] This Court has previously explained the concepts of res judicata,

collateral estoppel, claim preclusion, and issue preclusion in some detail:

“Res judicata consists of two preclusion concepts: issue preclusion and claim preclusion.” We have previously defined these two concepts in the following terms:

Issue preclusion refers to the effect of a judgment in foreclosing relitigation of a matter that has been litigated and decided. This effect also is referred to as direct or collateral estoppel. Claim preclusion refers to the effect of a judgment in foreclosing litigation of a matter that never has been litigated, because of a determination that it should have been advanced in an earlier suit[.]

The difference between issue and claim preclusion is largely “one of degree and emphasis[.]” However, “claim preclusion[ ] is broader than the issue preclusion function of collateral estoppel.” For example, claim preclusion “precludes relitigation of a claim . . . actually litigated or which could have been properly raised.” But issue preclusion “prevents relitigation only of issues actually litigated in a prior proceeding.” What is prohibited, then, under claim preclusion is the cause of action

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itself, but under issue preclusion, it “is the particular issue or fact common to both actions.”

Healy II, 2022 S.D. 43, ¶¶ 40–41, 978 N.W.2d at 798 (alterations and emphasis in

original) (citations omitted). Res judicata arguments are analyzed under a well-

established four-part test, which we have applied to both issue and claim

preclusion:

(1) the issue in the prior adjudication must be identical to the present issue, (2) there must have been a final judgment on the merits in the previous case, (3) the parties in the two actions must be the same or in privity, and (4) there must have been a full and fair opportunity to litigate the issues in the prior adjudication.

Id. ¶ 42, 978 N.W.2d at 799 (citation omitted).

[¶57.] With regard to claim preclusion, however, “we have generally not

required exacting ‘issue-identity’ with the earlier action” so that “our review is not

restricted to whether the specific question posed by the parties in both actions was

the same or whether the legal question posed by the nature of the suit was the

same.” Id. ¶ 44 (citation omitted). When analyzing claim preclusion “we look to

whether the second action ‘attempt[s] to relitigate a prior determined cause of

action[.]’” Id. (alterations in original) (citation omitted). “For purposes of [claim

preclusion], a cause of action is comprised of the facts which give rise to, or

establish, the right a party seeks to enforce. The test is a query into whether the

wrong sought to be redressed is the same in both actions.” Id. ¶ 45 (alteration in

original) (citation omitted). “If the claims arose out of a single act or dispute and

one claim has been brought to a final judgment, then all other claims arising out of

that same act or dispute are barred.” Id. (citation omitted).

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[¶58.] Regarding the first element—whether Bret is attempting in this action

to relitigate a previously-determined cause of action—we need look no further than

the federal district court’s decisions in Fox (the RICO action) and Healy III. In both

of those cases, the district court analyzed whether the claims were precluded under

res judicata. In the amended complaint Bret filed in Fox, he asserted that the

defendants in that action “repeatedly represented to [Bret], in documents mailed

over the course of seventeen years, that [Bret] owned 1/3 of the stock of [HRI],

which would give him at least a 1/3 interest in the [R]anch.” Specifically, Bret

alleged that in 2000, an agreement was signed in which Bret’s mother agreed to

“sell all of her shares in HRI to the three brothers, with each brother to acquire one-

third.” Bret made several other allegations regarding the ownership of HRI,

including that the “HRI shares issued in 1994 to Osborne, which were subsequently

transferred to Bret in 2000, were void because she failed to provide proper

consideration when she established the corporation.” Fox, 572 F. Supp. 3d at 734.

[¶59.] The defendants in Fox moved to dismiss Bret’s claims, arguing, inter

alia, that they were “barred by the doctrine of res judicata, specifically claim

preclusion based on Bret having litigated and lost related claims in [the] state court

action.” Id. at 736. Applying the four elements of res judicata, the district court

concluded first that the “underlying facts” giving rise to the causes of action in that

case were the same as the underlying facts in Healy I:

In the Amended Complaint, Bret claims the Defendants engaged in a RICO conspiracy to deceive him into believing he owned an interest in HRI to induce him into making substantial investments in HRI. Importantly, the RICO conspiracy Bret alleges stems from the same alleged fraudulent transfer of property interest from the partnership to HRI that formed the

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central theme of Bret’s state court action. See Healy [I], 934 N.W.2d at 564–65.

Id. at 743 (citation modified).

[¶60.] And more recently, in the action against this Court, the district court

noted that Bret’s prayer for relief included a declaration that Bret is the “owner of

two-thirds of all the outstanding shares of HRI capital stock.” The district court

concluded the “state law claims” of fraud “[arose] out of the same nucleus of facts

where ‘the wrong sought to be redressed is the same’ as in the prior cases.” Healy

III, 2023 WL 8653851, at *10. The district court further explained: “In Healy I,

Healy II, and the prior federal litigation [Fox], like in this case [Healy III], ‘the

wrong sought to be redressed’ is [Bret’s] assertion to greater ownership in HRI and

its assets[.]” Id. (emphasis added).

[¶61.] Through his motion to dismiss the petition for dissolution in the

present case, Bret has yet again attempted to assert greater ownership in HRI. As

the district court concluded, that very issue has been addressed and disposed of for

a variety of reasons in a number of prior cases. Bret has recalibrated the theories

behind his many lawsuits over the course of seven years of litigation, but neither

the nucleus of facts, nor the ultimate basis of many of his claims—ownership of

HRI—have varied. The district court in Fox recognized that “while Bret’s two

claims rely on different legal theories, that alone does not bar the application of res

judicata under South Dakota law.” Fox, 572 F. Supp. 3d at 744. In so holding, the

district court cited to this Court’s opinion in Farmer v. South Dakota Department of

Revenue & Regulation, where we held:

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When examining whether the question in one action was the same as in a subsequent action, our review is not restricted to whether the specific question posed by the parties in both actions was the same or whether the legal question posed by the nature of the suit was the same. Rather, we review whether the claims asserted in both suits arose out of a single dispute and whether one claim has been brought to a final judgment on the merits.

781 N.W.2d 655, 660 (S.D. 2010) (citation omitted).

[¶62.] We, therefore, conclude that the first element of our claim preclusion

test is satisfied because the issue raised by Bret in his motion to dismiss the

petition for dissolution—the ownership of HRI—was the same issue adjudicated in

several previous cases. The second element is likewise satisfied because the district

court in Healy III dismissed the ownership claim on the merits, which was affirmed

on appeal,11 and also in the actions preceding Healy III. See Healy II, 2022 S.D. 43,

¶¶ 52–53, 978 N.W.2d at 801 (“For purposes of res judicata, the term has come to be

applied to some judgments . . . that do not pass upon the substantive merits of a

claim. Our decision in [Healy I] determined that Bret’s legal rights were no longer

enforceable and that the various defendants faced no liability under the claims

asserted. Though the decision may not have examined the substantive merits of the

various claims, it was nonetheless a final judgment on the merits entitled to

preclusive effect because it settled the rights and obligations of the respective

parties.”) (citation modified).

[¶63.] For the third element of claim preclusion—the parties in the two

actions must be the same or in privity—we “look beyond the nominal parties” and

11. Healy v. Sup. Ct. of S.D., No. 24-1996, 2025 WL 999468 (8th Cir. April 3, 2025).

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treat “those whose interests are involved in the litigation and [those] who conduct

and control the action or defense” as the real parties who are bound by “any

judgment that may be rendered.” Matter of Guardianship of Janke, 500 N.W.2d

207, 209 (S.D. 1993) (citations omitted). Here, Bret was either a named plaintiff or

was acting as plaintiff and controlled the action for or on behalf of HRP. The other

parties to the present action—HRI, Bryce, and Barry—were parties within the

definition above in Healy I, Healy II, and Fox. The third element of the res judicata

test has been met.

[¶64.] The fourth and final element—a full and fair opportunity to litigate the

issues in the prior adjudication—has also been satisfied. The Court in Healy II

explained: “For a claim to be barred by res judicata, the claim need not have been

actually litigated at an earlier time. Rather, the parties only need to have been

provided ‘a fair opportunity to place their claims in the prior litigation.’” 2022 S.D.

43, ¶ 56, 978 N.W.2d at 802 (citation omitted). As we noted in Healy II, Bret was

aware of facts necessary to assert a greater ownership interest in the Ranch, in

Healy I, but he instead “elected to pursue different claims and remedies” and was,

therefore, foreclosed from asserting the ownership issue in subsequent cases. Id. at

¶ 59.

[¶65.] In sum, the basis for Bret’s challenge to the dissolution—the claimed

ownership of HRI—has been decided against him several times previously based on

judicial estoppel and res judicata, and such an argument is again precluded under

our settled principles of claim preclusion. The circuit court did not err in so

concluding. We must next determine whether the circuit court erred in determining

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Bret’s advancement of this precluded claim is sanctionable conduct under SDCL 15-

6-11(b)(1).

[¶66.] The circuit court found that Bret’s assertion of ownership of HRI via

his motion to dismiss the dissolution petition was not motivated by a belief in a

supported legal claim because such claim has been previously rejected as precluded.

The court thus found that Bret was instead motivated by a desire to harass or cause

unnecessary delay or needlessly increase the costs of litigation. Bret argues the

court erred in determining his motion to dismiss was motivated by an improper

purpose. We afford no presumption that this finding is correct. SDCL 15-6-11(e).

[¶67.] From our review of the facts of this case and the extensive history of

the litigation involving Bret, the circuit court’s conclusion that Bret violated SDCL

15-6-11(b)(1) was not clearly erroneous. For nearly a decade, Bret has battled with

his mother and brothers regarding the ownership of HRI and the Ranch. Bret has

asserted the same or similar claims of such ownership in five actions in both state

and federal courts and has appealed those courts’ decisions to this Court and the

Eighth Circuit. Each time these courts ruled against him, Bret reframed the issues

and his arguments and produced additional and sometimes contradictory evidence

in an attempt to resurrect the same claims of ownership.

[¶68.] Considering this history and the various courts’ decisions

unmistakably determining that Bret’s ownership claims were precluded many times

over, the circuit court could find that Bret asserted these actions for improper

purpose. See Crowley v. Spearfish Indep. Sch. Dist., 445 N.W.2d 308, 313 (S.D.

1989) (affirming a sanction award against a party after finding that “harassment

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was undertaken” by a party who had abused the court system by “continu[ing] to

use the courts to decide matters which have already been decided or which they

failed to urge in previous proceedings”); Kountze, 536 F.3d at 819 (affirming

sanctions where the district court determined that the prior action against a

particular named party was dismissed with prejudice, naming the same party “in

the current action must have been for an improper purpose” (citing Fed. R. Civ. P.

11(b)(1))); Buster, 104 F.3d at 1190, as amended on denial of reh’g (Mar. 26, 1997)

(holding the district court did not abuse its discretion in concluding that Buster’s

action “was brought to harass the Trustees,” noting it has held that “‘successive

complaints based upon propositions of law previously rejected may constitute

harassment under Rule 11’” (citation omitted)); Stone v. Baum, 409 F. Supp. 2d

1164, 1171 (D. Ariz. 2005) (holding that because plaintiffs were “repeatedly

informed that such repetitive suits are barred by res judicata, there can be no

conclusion except that Plaintiffs filed this case for an improper purpose, such as to

harass Albertsons and/or cause Albertsons undue litigation costs. Rule 11 sanctions

are warranted.”).

[¶69.] Based upon the number and frequency of the cases filed by Bret

against family members and others, the circuit court could reasonably find that

Bret’s unrelenting efforts to relitigate the same issues served no purpose other than

to harass or cause unnecessary delay or needlessly increase the cost of litigation.

The circuit court’s finding that Bret violated SDCL 15-6-11(b)(1) was not clearly

erroneous.

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b. Whether Bret’s reliance on the advice of counsel absolves him of responsibility.

[¶70.] Bret claims he relied “in good faith on at least a half dozen attorneys

and other experts regarding the sufficiency of HRP’s claims” and that he should not

be personally sanctioned. In support, Bret cites to Scanning Electron Microscopy

Inc. v. Institute For Scientific Information, Inc., where the plaintiff submitted an

affidavit detailing his discussions with his attorney and his attorney’s legal

research into the allegations. No. 81 C 01781, 1990 WL 36766, at *1 (N.D. Ill. Mar.

2, 1990). The court in that case noted there was no evidence offered “to rebut this

evidence that plaintiff relied in good faith on the advice of its attorney” nor was

there any evidence that “plaintiff misrepresented any facts” to his attorney. Id.

The court, therefore, held that it was “not a situation where a plaintiff, at little

expense to itself, has filed a ‘nuisance’ suit in an effort to obtain a quick settlement.

Rather, plaintiff’s conduct tends to indicate that it believed it had a good case. That

belief was based upon its lawyers’ advice.” Id. at *2. Here, neither Bret nor his

attorney have submitted any affidavits like in the case on which Bret relies.

[¶71.] Bret also relies on Taylor v. Collins, where the court held sanctions

were not warranted against the plaintiff, where the attorney admitted “that at all

times, [client] relied on [attorney’s] advice as to the legal and factual sufficiencies of

the action.” 493 S.E.2d 475, 480 (N.C. Ct. App. 1997). The court held, “[i]n light of

this evidence, we find that [client] in good faith relied on [attorneys] regarding the

legal sufficiency of his claims and thus met his duty of making a ‘reasonable

inquiry.’” Id. The North Carolina Supreme Court explained, however, that while

“good faith reliance on an attorney’s advice” may preclude sanctions against the

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party “under the legal sufficiency prong,” the court has “made it clear . . . that this

limitation applied only to the legal sufficiency prong and not the improper purpose

prong of Rule 11. That distinction was based on the belief that a represented party

should ‘be held responsible if his evident purpose is to harass, persecute, otherwise

vex his opponents, or cause them unnecessary cost or delay.’” Brooks v. Giesey, 432

S.E.2d 339, 342–43 (N.C. 1993) (citations omitted).

[¶72.] Here, beyond a bare assertion that Bret relied on the advice of counsel,

there is no evidence in the record to support his claimed reliance. While we do not

question Bret’s claim that he has expended over $300,000 in legal fees, in light of

the numerous prior decisions in which courts have ruled that his claims are time-

barred and precluded by res judicata, and the repeated sanctions accompanying

such rulings, we view Bret’s continued quest to disprove ownership of HRI and/or

the Ranch to be nothing short of harassing. As we determined above, the apparent

purpose behind Bret’s relitigation of these issues is to harass, cause unnecessary

delay, or needlessly increase the cost of litigation. As such, Bret’s purported

reliance on counsel is not a shield that he can hide behind to avoid the consequences

of his own active participation in the numerous lawsuits in which he continues to

make claims that have been rejected on several occasions. Under these

circumstances, the circuit court did not abuse its discretion in holding Bret

accountable for the harassing and improper sanctionable conduct under SDCL 15-6-

11(c).

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c. Whether the $240,000 monetary sanction is excessive.

[¶73.] Bret did not directly challenge or address the amount of the sanction in

his opening appellate brief, but instead waited until his reply brief to do so.

Accordingly, we doubt whether the issue is properly before us. See Weiland v.

Bumann, 2025 S.D. 9, ¶ 50, 18 N.W.3d 148, 160 (where issue was not raised in an

opening brief, we questioned whether the argument was properly before us);

Ellingson v. Ammann, 2013 S.D. 32, ¶ 10, 830 N.W.2d 99, 102 (“A party may not

raise an issue for the first time on appeal, especially in a reply brief when the other

party does not have the opportunity to answer.”). Nevertheless, the importance of

the issue and amount of the sanction warrant exercising our discretion to address it.

[¶74.] In determining whether the sanction imposed by the circuit court was

an abuse of discretion, we are guided both by statute and other principles. SDCL

15-6-11(c)(2) directs that “[a] sanction imposed for violation of this rule shall be

limited to what is sufficient to deter repetition of such conduct or comparable

conduct by others similarly situated.” See also Smizer, 2016 S.D. 3, ¶ 18, 873

N.W.2d at 703 (“We have said that the purpose of sanctions under SDCL 15-6-11 is

to deter abuse by parties and counsel.” (citation omitted)). Evidence of bad faith is

not required. Id. Subject to some limitations, the sanction may consist of or include

a nonmonetary sanction, such as filing restrictions, an order to pay a penalty into

court, or under specific circumstances, an order directing payment of reasonable

attorney fees and other expenses incurred as a direct result of the violation. SDCL

15-6-11(c)(2).

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[¶75.] When imposing sanctions, SDCL 15-6-11(c)(3) requires that the court

“describe the conduct determined to constitute a violation of this rule and explain

the basis for the sanction imposed.” This requirement “facilitate[s] effective

appellate review.” Smizer, 2016 S.D. 3, ¶ 18, 873 N.W.2d at 703 (citations omitted).

While a court’s “inherent powers must be exercised with restraint and discretion,” a

“primary aspect of that discretion is the ability to fashion an appropriate sanction

for conduct which abuses the judicial process.” Schlafly v. Eagle F., 970 F.3d 924,

936–37 (8th Cir. 2020) (citation omitted). The courts’ sanctioning power should be

used “sparingly.” Cromer v. Kraft Foods N. Am., Inc., 390 F.3d 812, 817 (4th Cir.

2004).

[¶76.] Bret first argues the amount of the monetary sanction is excessive

because his conduct “was neither improper nor negligent.” We disagree for all the

above reasons we have found justifying sanctions.

[¶77.] Bret also relies on the fact that he was represented by counsel. While

we have determined this fact does not insulate Bret from being sanctioned for his

own purposeful harassing conduct, whether he was acting on the advice of legal

counsel may be a relevant factor when considering the amount of sanction needed to

deter further conduct of this nature. Cf. Navarro-Ayala v. Nunez, 968 F.2d 1421,

1426 n.4 (1st Cir. 1992) (concluding that reliance on counsel “is a factor to be

considered in determining what sanction may be appropriate”).

[¶78.] The circuit court based its sanctions against Bret on the fact that he

had previously been sanctioned over $120,000, which the court found “had no effect”

on Bret. The court stated, “It is the intent of this [c]ourt to impress upon Mr. Healy

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that his actions have consequences and should not continue, and it is the finding of

this [c]ourt that the doubling of his past sanctions will do so.”

[¶79.] The circuit court’s finding that past sanctions have had no effect on

Bret is entirely accurate, and the court was fully justified in its attempt to impress

upon Bret that his actions have consequences. See Willhite v. Collins, 459 F.3d 866,

869 (8th Cir. 2006) (concluding the amount of the monetary sanction was

“substantial, but not unwarranted”). In Willhite, the court concluded that although

an award of sanctions should be “no greater than sufficient to deter future

misconduct by the party,” a large award was necessary to deter similar misconduct,

noting that the sanctioned attorney had been sanctioned multiple times in the past.

Id. (citation omitted). See also In re Kunstler, 914 F.2d 505, 525 (4th Cir. 1990)

(holding the court could increase a sanction if there had been previous sanctions

“because such conduct might indicate that the previous sanction was not enough to

deter the repetition of the offense”). Cf. Giangrasso v. Kittatinny Reg’l High Sch.

Dep’t of Educ., 865 F. Supp. 1133, 1141 (D.N.J. 1994) (holding “the enormity of this

situation demands extraordinary sanctions,” noting the plaintiff “abused the legal

system to harass defendants” and that previous attempts at deterrence were

unsuccessful). For many of the same reasons, a substantial monetary sanction may

be warranted here. Despite prior sanctions and efforts to deter Bret’s conduct, he

has continued to abuse our legal system by asserting claims that have been raised

or rejected in several prior proceedings.12

12. The dissent finds disproportionality in the sanction imposed on Bret “relative to the one imposed on his lawyer whose education, training, and professional (continued . . .) -41- #30666

[¶80.] However, while deterrence is one of several factors that should be

considered, a sanctioning court should also consider the party’s ability to pay the

sanction and which “sanction constitutes the least severe sanction that will

adequately deter the undesirable conduct.” Pope v. Fed. Express Corp., 974 F.2d

982, 985 (8th Cir. 1992) (citation omitted); Kunstler, 914 F.2d at 523 (holding the

court should consider the minimum amount to deter party’s conduct and party’s

ability to pay); 61A Am. Jur. 2d Pleading § 533 (noting failure to consider equitable

factors such as the ability to pay could amount to an abuse of discretion and that

“although Rule 11 sanctions should be severe enough to deter future violations, they

should not be financially ruinous”).

[¶81.] Further, a monetary sanction is not the only option. The court in

Doering v. Union County Board of Chosen Freeholders, held that courts are

encouraged to “consider a wide range of alternative possible sanctions for violations

of [Rule 11].” 857 F.2d 191, 194 (3d Cir. 1988). The sanction is “appropriate when

it is the minimum that will serve to adequately deter the undesirable behavior.” Id.

“The language of Rule 11 evidences the critical role of judicial discretion” to craft a

sanction to fit the situation. Id. Further, where the court “decides to award a

________________________ (. . . continued) role placed him in a far superior position to judge the viability and efficacy of Bret’s legal positions.” But, this ignores that Bret was the driving force behind these actions, both before and after Volesky’s representation of him. Further, in addition to the monetary sanction against him, Volesky was reported to the State’s disciplinary board, underwent the scrutiny of disciplinary proceedings, including a public hearing, and his license to practice law in this state was ultimately suspended for 90 days. Volesky’s role as lawyer and adviser to Bret is reflected in the differing type of sanctions imposed on him, which also, by their nature, carried a significant financial penalty from lost income.

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monetary sanction, . . . the total amount of such a sanction (as well as the initial

decision whether to impose such a sanction) should be guided by equitable

considerations.” Id. at 195.

[¶82.] We have not previously required that the courts consider the ability to

pay when fashioning an appropriate sanction for violation of SDCL 15-6-11(b), nor

have we expressly stated that the courts should consider non-monetary sanctions.

Therefore, we find no fault in the circuit court’s failure to do so here. However, it is

the Court’s opinion that the ability to pay a monetary sanction is an important

consideration and that non-monetary sanctions should also be considered.

Accordingly, we affirm the circuit court’s conclusion that Bret violated SDCL 15-6-

11(b), that sanctions can be imposed against him personally, and that sanctions are

warranted. However, we remand to the circuit court for consideration of an

appropriate sanction, be it monetary, non-monetary, or some combination of the

two, and taking into account all the considerations discussed herein.

Appellate Attorney Fees

[¶83.] HRI requests appellate attorney fees and costs in the amount of

$9,330.88 pursuant to SDCL 15-17-51. Under SDCL 15-26A-87.3, appellate

attorney fees may be awarded “only where such fees are permissible at the trial

level.” Matter of Fred Petersen Land Tr., 2023 S.D. 44, ¶ 41, 995 N.W.2d 84, 93

(citation omitted). SDCL 15-17-51 provides that where a party’s “requested relief is

denied and if the court determines that it was frivolous or brought for malicious

purposes, the court shall order the party whose claim, cause of action, or defense

was dismissed or denied to pay part or all expenses incurred by the party defending

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the matter, including reasonable attorneys’ fees.” Given our disposition on appeal,

we conclude Bret’s appeal was not frivolous or filed for malicious purposes.

Therefore, we decline to award HRI its appellate attorney fees.

Conclusion

[¶84.] The issue that the circuit court found was falsely sworn to and that

was the basis for the imposition of sanctions—the ownership of HRI—has been

repeatedly addressed by both state and federal courts which have determined that

Bret’s claims are precluded. The circuit court did not clearly err in finding that

when raising the same claims in an effort to dismiss the petition for supervised

dissolution, Bret was motivated by an improper purpose, in violation of SDCL 15-6-

11(b)(1). The circuit court did not abuse its discretion when determining that Rule

11 sanctions were warranted under the circumstances. We therefore affirm this

determination. However, because we hold that a sanctioning court should also

consider non-monetary sanctions and the ability to pay a monetary sanction, we

vacate the circuit court’s imposition of monetary sanctions and remand to the circuit

court to reconsider an appropriate sanction against Bret.

[¶85.] Affirmed in part, vacated in part, and remanded for further

proceedings consistent with this opinion.

[¶86.] JENSEN, Chief Justice, and MYREN, Justice, concur.

[¶87.] SALTER and DEVANEY, Justices, dissent.

[¶88.] GUSINSKY, Justice, not having been a member of the Court at the

time this action was considered by the Court, did not participate.

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SALTER, Justice (dissenting).

[¶89.] I believe the circuit court lacked authority under SDCL 15-6-11 (Rule

11) to impose a non-compensatory monetary sanction on a represented party under

the circumstances here. I would vacate the Rule 11 sanction against Bret and

respectfully offer this explanation.

[¶90.] A Rule 11 sanction must be based upon a presentation to the court of a

pleading, written motion, or other paper that does not meet one or more of the

certification requirements in Rule 11(b). The basis of the circuit court’s Rule 11

sanction against Bret here was his statement concerning the ownership of HRI, an

issue that is somewhat obfuscated by the shifting sands of his litigation strategies

in the ongoing dispute over the Healy Ranch. As the Court’s opinion acknowledges,

the difficulty Bret confronted in this case, and in others, is less about factual

inaccuracy and more about a legal impediment—the inability to litigate his factual

claims about HRI, HRP, and the ownership of Healy Ranch due to the claim

preclusion aspects of res judicata.

[¶91.] “[B]ecause Rule 11 carefully assigns responsibility between

represented parties and their counsel, only attorneys may be held liable where the

basis of a sanctions award is the frivolousness of a party’s legal position.” Dearborn

St. Bldg. Assocs., LLC v. Huntington Nat’l Bank, 411 F. App’x 847, 852 (6th Cir.

2011) (unpublished) (citing Fed. R. Civ. P. 11(c)(5)(A)). Consequently, Volesky alone

was responsible for making legal arguments, and he was, for this reason,

appropriately subject to the sanction the circuit court imposed.

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[¶92.] But a court’s ability to impose a non-compensatory monetary sanction

upon a represented party, like Bret, is different. Bret was not responsible for the

legal arguments in this case; his lawyer, Volesky, was. The circuit court’s finding

that Bret violated Rule 11(b)(1) is a corollary of Volesky’s advocacy. This is

apparent from the court’s explanation:

Objectively and on its face this action is frivolous defined. No rational argument exists to support it, no basis to argue for change has any chance of success, and no reasonable person should expect a favorable ruling. It is clear and the finding of this [c]ourt that Mr. Healy is motivated to bring this action not by any belief in a supported legal claim, as those have all been turned away at the courthouse steps, but rather a clear and continuing effort to harass or cause unnecessary delay or needlessly increase the cost of litigation.

[¶93.] Bret’s purpose was deemed improper precisely because it was founded

upon a frivolous legal position that his lawyer should have counseled against,

making the court’s Rule 11(b)(1) finding for Bret and its frivolous finding for

Volesky effectively one and the same. And although Bret may bear his share of

responsibility for the outcomes over the course of the previous litigation, he cannot

be sanctioned for a frivolous legal position taken in this action without contravening

Rule 11(c)(2)(A).

[¶94.] But even if this were not the case, it is at least true that the sanction

imposed on Bret is disproportionate relative to the one imposed on his lawyer whose

education, training, and professional role placed him in a far superior position to

judge the viability and efficacy of Bret’s legal positions. This imbalance is

particularly stark in light of the principle underlying Rule 11(c), which provides

that “the ability to sanction a [represented party] is derivative, in part,” to the

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party’s attorney violating Rule 11(b)’s certification requirement. 5A Wright &

Miller’s Federal Practice & Procedure § 1336.2, Westlaw (database updated Sept.

2025). But this rule becomes inverted in this case with a punitive Rule 11 sanction

for a represented party that is twenty-four times more severe than the monetary

sanction imposed on his lawyer.

[¶95.] The better course here is, in my view, to vacate the monetary sanction

against Bret and remand the case to allow the circuit court to consider other types

of sanctions, such as a compensatory award of attorney fees.

[¶96.] DEVANEY, Justice, joins this writing.

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