THE SUPREME COURT, STATE OF WYOMING
2026 WY 95
APRIL TERM, A.D. 2026
August 25, 2026
DILLINGER’S LLC, a Wyoming limited liability company and RYAN CLEMENT, an individual
Appellants (Defendants), S-25-0296
v.
CR-GTD, LLC and EFTI, LLC, a Wyoming limited liability company,
Appellees (Plaintiffs).
Appeal from the District Court of Laramie County The Honorable Nathaniel S. Hibben, Judge
Representing Appellant:
John G. Knepper of Law Office of John G. Knepper, LLC, Cheyenne, Wyoming. Argument by Mr. Knepper.
Representing Appellee:
Holly L. Tysse and Bobbi K. Owen of Crowley Fleck PLLP, Casper, Wyoming. Argument by Ms. Owen.
Before BOOMGAARDEN, C.J., and GRAY, FENN, JAROSH, and HILL, JJ.
NOTICE: This opinion is subject to formal revision before publication in Pacific Reporter Third. Readers are requested to notify the Clerk of the Supreme Court, Supreme Court Building, Cheyenne, Wyoming 82002, of any typographical or other formal errors so that correction may be made before final publication in the permanent volume.
FENN, Justice.
[¶1] Appellants, Dillinger’s, LLC (Dillinger’s), and Ryan Clement, seek relief from a preliminary injunction granted by the district court to Appellees, Cowboy Racing, LLC (Cowboy Racing),1 and EFTI, LLC (EFTI), during an underlying lawsuit relating to the management and ownership of Cowboy Racing. Appellants assert the district court improperly resolved a central dispute regarding the propriety of Mr. Clement’s removal as a Manager and the interpretation of the Operating Agreement at the preliminary injunction stage, before the parties had an opportunity for notice and discovery. We affirm.
ISSUE
[¶2] Appellants raise two issues, which we consolidate and rephrase as follows:
Did the district court improperly and definitively resolve questions about the management of Cowboy Racing at the preliminary injunction stage?
FACTS
[¶3] Ryan Clement is the sole member of Dillinger’s. EFTI is owned and operated by members of the Edwards family and managed by William Edwards. On October 20, 2023, EFTI and Dillinger’s executed an Operating Agreement to form and govern Cowboy Racing. EFTI held a 51% interest in Cowboy Racing, and Dillinger’s held the remaining 49%. Cowboy Racing hosts live horse races and operates off-track betting locations in Wyoming.
[¶4] The Operating Agreement appointed Mr. Edwards and Mr. Clement as the “initial Managers” of Cowboy Racing. It also authorized the appointment of additional Managers and contained two provisions governing the removal of a Manager. Section 5.4 states in relevant part:
5.4 Limitations on Authority – Majority Interest. Notwithstanding any other provision of this Operating Agreement, until such time as (i) all outstanding debts of Company due to EFTI, LLC or Affiliates of EFTI, LLC are paid in full, and (ii) the Company is operating profitably for at least six (6) consecutive months, no Manager shall cause or commit the Company to do any of the following without the express written consent of Members holding at least a Majority Interest.
1 While this appeal was pending, Cowboy Racing changed its name to CR-GTD, LLC.
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p. cause Ryan Clement to be removed as a Manager for any reason other than for cause . . . .
[¶5] Section 5.11 states:
5.11 Removal. At a meeting called expressly for that purpose, any Manager may be removed at any time for gross negligence, fraud, deceit or intentional misconduct which had a material adverse effect on the Company, or if the Manager is adjudicated incompetent by a [c]ourt of competent jurisdiction. The removal of a Manager who is also a Member shall not affect the Manager’s rights as a Member and shall not constitute a withdrawal of a Member.
[¶6] On February 11, 2025, “the Majority Membership of Cowboy Racing” held a special meeting to “remove and replace a Manager,” pursuant to Section 5.11 of the Operating Agreement. At this meeting, EFTI decided to remove Mr. Clement as a Manager ostensibly “in response” to his unilateral decision to incur attorney’s fees. Mr. Clement’s removal was confirmed through a resolution dated June 2, 2025. This resolution recognized Mr. Clement had been removed at the February 2025 Special Meeting due to his “unilateral and unauthorized expenditures[.]” However, it also indicated EFTI did not need cause to remove Mr. Clement as a Manager, and it stated: “IT IS HEREBY RESOLVED AND REAFFIRMED that [EFTI], the Majority Interest holder of [Cowboy Racing], has exercised its right to remove and replace Mr. Clement as a Manager of [Cowboy Racing] as of February 11, 2025, with or without ‘cause[.]’” Although Mr. Edwards informed Mr. Clement on multiple occasions that Mr. Clement had no authority to bind Cowboy Racing to any agreement or contract, Mr. Clement continued to contact third parties purportedly acting on behalf of Cowboy Racing, and he made representations to those third parties regarding the development of a sports complex as part of Cowboy Racing’s operations.
[¶7] In July 2025, Cowboy Racing and EFTI filed suit against Dillinger’s and Mr. Clement seeking: a declaration Mr. Clement had no right to act on behalf of Cowboy Racing; a declaration EFTI had a contractual right to purchase Dillinger’s interest in Cowboy Racing either under the automatic call provision of the Operating Agreement or a letter of intent (LOI) that had been signed by the parties on March 13, 2025; damages for the alleged breach of the LOI by Dillinger’s; an alternative claim for breach of the duty of good faith and fair dealing; and a preliminary injunction precluding Mr. Clement from holding himself out as a Manager or someone with authority to make decisions on behalf of Cowboy Racing until the court ruled on the declaratory judgment claim. Cowboy
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Racing and EFTI also filed a motion for preliminary injunction, arguing “[i]njunctive relief [was] required to prevent further and irreparable injury to Cowboy Racing, its investments, reputation, goodwill, and overall business.”
[¶8] In his response to the motion for a preliminary injunction, Mr. Clement asserted Mr. Edwards’s actions were “without legal basis,” and he admitted “he continues to describe himself informally as an owner of Cowboy Racing.” He denied attempting to negotiate contracts on behalf of the company without Mr. Edwards’s involvement. Mr. Clement argued Cowboy Racing and EFTI’s reference to a potential loss of goodwill was “speculative and conclusory” and was not enough to constitute irreparable harm under the “high bar” needed for preliminary injunctions. Although EFTI and Cowboy Racing framed its request as a motion for a preliminary injunction, Mr. Clement asserted they were actually asking the district court to determine they had correctly interpreted the Operating Agreement and properly removed Mr. Clement as a Manager before he had the opportunity to engage in discovery and present evidence in support of his position. He denied his behavior was sufficient to justify a for cause removal and argued Cowboy Racing and EFTI’s proposed interpretation of the Operating Agreement created a conflict between Section 5.4 and Section 5.11.
[¶9] In reply, Cowboy Racing and EFTI asserted they had alleged sufficient facts to demonstrate irreparable harm. They claimed Mr. Clement’s actions posed a direct and substantial threat to Cowboy Racing’s “good will and business reputation” and could cause the Company to lose its license, which would prevent it from being able to operate. They also argued they had demonstrated a clear showing of probable success on the merits because Mr. Clement had either been removed for cause under Section 5.11 of the Operating Agreement, or EFTI could remove him without cause under Section 5.4.
[¶10] The district court held an evidentiary hearing on the motion for preliminary injunction on October 22, 2025. After considering the evidence presented at that hearing, the district court granted the preliminary injunction.2 In the written order issued after the hearing, the district court found Cowboy Racing and EFTI “made a probable showing of irreparable injury to support a preliminary injunction.” The district court found they had “demonstrated probable loss of reputation, good will, and injury to the ongoing course of business if injunctive relief [was] not granted.” The district court also found Cowboy Racing and EFTI had “shown [a] high probability of success on the merits of their declaratory judgment claim against [Mr.] Clement regarding his status as a Manager of [Cowboy Racing].” The district court “conclude[d] the Operating Agreement [was] clear.
2 This hearing was not reported, and the Appellants did not prepare a statement of the evidence adduced at that hearing pursuant to Rule 3.03 of the Wyoming Rules of Appellate Procedure. We will presume the order entered after the hearing accurately sets forth the district court’s oral ruling. See Olsen v. Olsen, 2011 WY 30, ¶ 8, 247 P.3d 77, 80 (Wyo. 2011) (“Lacking a properly authenticated transcript, or an appropriate substitute for the transcript, the reliability of the district court’s decision and the competency of the evidence upon which that decision is based must be presumed.”)
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[Cowboy Racing and EFTI] have demonstrated that [Mr.] Clement was removed as a Manager by [EFTI] under Section 5.4 of the Operating Agreement . . . .” The district court held “the Operating Agreement permits [Mr.] Clement to be removed as Manager by [EFTI] without cause.” The district court’s order stated:
ORDER OF THE COURT
The [c]ourt hereby issues an injunction finding [Mr.]
Clement has been lawfully removed as a Manager of [Cowboy Racing]. [Mr.] Clement is enjoined from holding himself out as a Manager or other individual with authority to bind [Cowboy Racing].
The [c]ourt makes no findings or conclusions regarding [Mr.] Clement or [Dillinger’s]’s interest in Cowboy Racing. Based on the evidence presented at the preliminary hearing, the [c]ourt makes no findings or conclusions that whether [sic] [Mr.] Clement has interfered with [Cowboy Racing]’s business dealings. Further, this [c]ourt’s [o]rder does not restrain [Mr.] Clement’s First Amendment right to speak about [Cowboy Racing], so long as he does not do so as a purported Manager or decision[ ]maker for the company. [Mr.] Clement is not restrained from expressing any disagreements he may have with the Edwards family, or his disagreements with this [c]ourt’s ruling.
The [c]ourt finds that pursuant to Wyo. R. Civ. P. 65(c), a bond of $1,000 is sufficient and proper to provide security to pay possible costs and damages sustained by [Mr.] Clement in the event he is found to have been wrongfully enjoined or restrained.
WHEREFORE, IT IS HEREBY ORDERED: [Mr.]
Clement is enjoined from acting or holding himself out as a Manager or decision[ ]maker for [Cowboy Racing].
IT IS FURTHER ORDERED: Plaintiffs shall deposit a $1,000 bond with the Clerk of District Court for the First Judicial District within two (2) business days of entry of this Order.
This Preliminary Injunction Order shall remain in place throughout this litigation or until such time as terminated by
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the [c]ourt.
This appeal timely followed.
STANDARD OF REVIEW
[¶11] Although a preliminary injunction is authorized by statute,“[b]y its nature, however, it remains a form of equitable relief. We therefore review an order granting a preliminary injunction for an abuse of discretion.” Degenfelder v. Wyo. Educ. Ass’n, 2026 WY 54, ¶ 19, 589 P.3d 346, 353–54 (Wyo. 2026) (citation modified); Wyo. Stat. Ann. § 1-28-102 (2025). We review the district court’s factual findings for clear error and its conclusions of law de novo. Brown v. Best Home Health & Hospice, LLC, 2021 WY 83, ¶ 9, 491 P.3d 1021, 1026 (Wyo. 2021). “A finding of fact is clearly erroneous when, although there is evidence to support it, the reviewing court on the entire evidence is left with the definite and firm conviction that a mistake has been committed.” Id. (quoting Pagel v. Franscell, 2002 WY 169, ¶ 7, 57 P.3d 1226, 1229 (Wyo. 2002)). “[W]e review the evidence in the light most favorable to the prevailing party.” Id. (citing Wyo-Ben, Inc. v. Van Fleet, 2015 WY 146, ¶¶ 20, 31, 361 P.3d 852, 858, 861 (Wyo. 2015)).
[¶12] The purpose of a preliminary injunction is to preserve the status quo during pending litigation until the merits of the action can be determined. Degenfelder, 2026 WY 54, ¶ 20, 589 P.3d at 354 (quoting Brown, 2021 WY 83, ¶ 7, 491 P.3d at 1026). A preliminary injunction will be granted only “upon a clear showing of probable success on the merits of the suit and possible irreparable injury to the plaintiff, lest the proper freedom of action of the defendant be circumscribed when no wrong has been committed.” Id. “An injury is irreparable where it is of a peculiar nature, so that compensation in money cannot atone for it.” Brown, ¶ 7, 491 P.3d at 1026 (citation omitted).
DISCUSSION
[¶13] To obtain a preliminary injunction, EFTI and Cowboy Racing had to show a likelihood of success on the merits of their declaratory judgment claim and that they would suffer irreparable harm if the district court did not issue the injunction. Degenfelder, 2026 WY 54, ¶ 42, 589 P.3d at 358; Brown, 2021 WY 83, ¶ 7, 491 P.3d at 1026. Unlike most appeals from the grant of a preliminary injunction, Mr. Clement does not allege Appellees failed to demonstrate irreparable harm or a likelihood of success on the merits. Instead, he claims the district court’s ruling was “procedurally irregular” because, rather than granting a preliminary injunction, the district court effectively issued “a legal ruling on the meaning of conflicting provisions within the company’s Operating Agreement.” Mr. Clement claims it was improper for the district court to “definitively resolve any questions about the management of Cowboy Racing by interpreting the LLC’s Operating Agreement as a matter of law.” He asserts the district court “resolve[d] a key disagreement in this case without notice and without discovery[,]” by issuing an injunction which “holds that Mr.
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Clement can be lawfully removed from his position as co-manager of Cowboy Racing by [Appellees] without cause.”
[¶14] Appellees assert the district court “was well within its authority to interpret the Operating Agreement and make a preliminary ruling based upon the arguments and evidence presented at [that] stage in the proceedings.” They assert nothing in the district court’s order precludes Appellants from “engag[ing] in the typical discovery, motions practice, and presentation of evidence and theories at trial.”3
[¶15] “Generally, a preliminary injunction will not be awarded where its effect is to give the principal relief plaintiff seeks without bringing the cause to trial.” Simpson v. Petroleum, Inc., 548 P.2d 1, 3 (Wyo. 1976) (citations omitted). Under Rule 65(a)(2) of the Wyoming Rules of Civil Procedure (W.R.C.P.), the district court may order the trial on the merits to be “advanced and consolidated” with the hearing on the application for the preliminary injunction either “[b]efore or after beginning the hearing on a motion for a preliminary injunction . . . .” Although there is nothing in the language of W.R.C.P. 65(a)(2) describing the type of notice that is required prior to the district court ordering such a consolidation, our case law interpreting W.R.C.P. 65(a)(2) and the case law interpreting its federal counterpart unmistakably requires “some form of notice” to be given. See Simpson, 548 P.2d at 2 (stating “the parties must have some form of notice” that a hearing on a preliminary injunction has been consolidated with a trial on the merits); Univ. of Texas v. Camenisch, 451 U.S. 390, 395, 101 S. Ct. 1830, 1834, 68 L. Ed. 2d 175 (1981) (stating before the court may order consolidation of a preliminary injunction and “an expedited decision on the merits” under F.R.C.P. 65(a)(2), the parties should “receive clear and unambiguous notice of the court’s intent to consolidate the trial and the hearing either before the hearing commences or at a time which will still afford the parties a full opportunity to present their respective cases.”). There is nothing in the record to indicate the district court ever notified the parties of its intent to consolidate the proceedings in this case. Therefore, the parties “appeared at the hearing expecting to defend only against the granting of a preliminary injunction.” Simpson, 548 P.2d at 2. They did not expect to “walk away from that hearing saddled with” an order that resolved the declaratory judgment claim regarding the interpretation of the removal provisions of the Operating Agreement. Id.
[¶16] Although the proceedings had not been consolidated, the district court phrased its order as a final conclusion Mr. Clement was lawfully removed as a Manager of Cowboy Racing. It should not have done so. See Brown, 2021 WY 83, ¶ 12, 491 P.3d at 1027 (holding it was improper for the district court to phrase its preliminary injunction ruling as a final conclusion on the interpretation of a non-compete agreement when there had been 3 At oral arguments, Appellees again stated the district court’s order was only a “preliminary ruling” on the interpretation of the Operating Agreement, and the declaratory judgment claim remains subject to discovery while proceedings are ongoing. Appellees further conceded they would not attempt to argue the district court had made a final ruling regarding the interpretation of the Operating Agreement that had become the law of the case.
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no consolidation). “When ruling on a request for a preliminary injunction, the court does not make a final decision on the merits; it considers whether the petitioner has clearly shown it is likely to succeed in proving its claim.” Id. Although the district court should not have phrased its order as a final conclusion, this does not merit automatic reversal. See id. Instead, our task on appeal is to determine whether the district court could have reasonably concluded Cowboy Racing and EFTI were likely to succeed on the merits by proving Mr. Clement had been lawfully removed as a Manager. See id. at ¶ 13, 491 P.3d at 1027.
[¶17] To determine whether EFTI and Cowboy Racing were likely to succeed on the merits, the district court necessarily had to interpret the Operating Agreement. See, e.g., Brown, 2021 WY 83, ¶¶ 10–31, 491 P.3d at 1027–32 (interpreting a non-compete provision in a contract to determine if plaintiff was likely to succeed on the merits or its request for a preliminary injunction enjoining defendants from working for competitors while the litigation was pending); Lengyel-Fushimi v. Bellis, 242 A.D.3d 727, 730–32 (N.Y. App. Div. 2025) (interpreting a company’s operating agreement to determine if the plaintiff was likely to succeed on the merits of his request for a preliminary injunction enjoining the other members from removing him as a manager); Apple Glen Crossing, LLC v. Trademark Retail, Inc., 784 N.E.2d 484, 488–90 (Ind. 2003) (interpreting a company’s operating agreement to determine if plaintiff was likely to succeed on the merits of its request for a preliminary injunction enjoining its removal as a manager). In undertaking that analysis, the district court first had to determine whether the Operating Agreement was ambiguous. See, e.g., Van Vlack v. Van Vlack, 2023 WY 104, ¶ 20, 537 P.3d 751, 757 (Wyo. 2023). The district court concluded the Operating Agreement was unambiguous, and Section 5.4 authorized EFTI and Cowboy Racing to remove Mr. Clement without cause. Mr. Clement argues the district court erred and the Operating Agreement is ambiguous because it contains conflicting provisions regarding whether he can be removed without cause.
[¶18] “Contract interpretation is a matter of law which we consider de novo.” Jones v. Young, 2025 WY 130, ¶ 44, 580 P.3d 1026, 1038 (Wyo. 2025) (citation omitted). A contract is ambiguous if its meaning is obscure “because of indefiniteness of expression, or because a double meaning is present.” Id. at ¶ 46, 580 P.3d at 1038 (quoting Van Vlack, ¶ 20, 537 P.3d at 757). Our standard for interpreting contracts is well known:
the words used in the contract are afforded the plain meaning that a reasonable person would give them. When the provisions in the contract are clear and unambiguous, the court looks only to the “four corners” of the document in arriving at the intent of the parties. In the absence of any ambiguity, the contract will be enforced according to its terms because no construction is appropriate.
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Id. at ¶ 45, 580 P.3d at 1038 (quoting Morrison v. Hinson-Morrison, 2024 WY 96, ¶ 16, 555 P.3d 944, 952 (Wyo. 2024). “If two provisions of the same contract irreconcilably conflict with each other, the language of the contract is ambiguous.” Larson v. Burton Constr., Inc., 2018 WY 74, ¶ 37, 421 P.3d 538, 549 (Wyo. 2018) (Kautz & Davis, JJ., dissenting) (quoting Klapp v. United Ins. Grp. Agency, Inc., 468 Mich. 459, 467, 663 N.W.2d 447, 453 (2003)). However, we construe the contract as a whole, attempting to avoid rendering any portion meaningless, and “[w]e strive to reconcile by reasonable interpretation any provisions which apparently conflict before adopting a construction which would nullify any provision.” Purcella v. Purcella, 2011 WY 124, ¶ 14, 258 P.3d 730, 734–35 (Wyo. 2011) (citation omitted).
[¶19] In this case, Section 5.4 prohibits a “Manager” from “caus[ing] Ryan Clement to be removed as a Manager for any reason other than cause” “without the express written consent of Members holding at least a Majority Interest” until certain debts have been paid and Cowboy Racing has been operating profitably for at least six months. Section 5.2 of the Operating Agreement appointed Mr. Edwards and Mr. Clement as the “initial Managers,” but allowed the number of Managers to be changed “by the affirmative vote of Members holding a Majority Interest . . . .” Each Manager would “hold office until . . . removed pursuant to Section 5.[11]4.” As discussed above, Section 5.11 allows a Manager to be removed “for gross negligence, fraud, deceit or intentional misconduct” at a meeting that is called expressly for the purpose of removing that Manager.
[¶20] Contrary to Mr. Clement’s assertion, these provisions do not irreconcilably conflict or render the Operating Agreement ambiguous. The Operating Agreement can be given a reasonable interpretation that reconciles any apparent conflict between these provisions. See Purcella, 2011 WY 124, ¶ 14, 258 P.3d at 734–35. Under Section 5.11, any Manager could call a special meeting for the purpose of removing another Manager “for gross negligence, fraud, deceit or intentional misconduct.” However, if a Manager, like Mr. Edwards, wanted to remove Mr. Clement as a Manager for reasons other than those listed in Section 5.11, then under Section 5.4, he (or she) needed the “express written consent of Members holding at least a Majority Interest.” When these provisions are read together, the Operating Agreement provides two alternative methods for removing Mr. Clement, and these provisions do not irreconcilably conflict with each other. The district court did not err in its preliminary determination that the Operating Agreement is unambiguous.
[¶21] The district court’s order only discusses Appellees’ likelihood of success on the merits under its preliminary interpretation of Section 5.4.5 When viewed in a light most 4 This portion of the Operating Agreement refers to Section 5.9, which pertains to indemnification of Managers and employees. This appears to be a typographical error, and it is Section 5.11 that relates to the removal of Managers. 5 When viewed in a light most favorable to Appellees, the record also supports a conclusion Cowboy Racing and EFTI were likely to succeed on the merits of proving Mr. Clement had been removed for cause under
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favorable to Appellees, the record supports a conclusion Cowboy Racing and EFTI were likely to succeed on the merits of proving Mr. Clement had been removed with the express written consent of the Members holding a Majority Interest under Section 5.4. The record shows EFTI holds a 51% interest in Cowboy Racing and represented the majority membership. It further shows EFTI held a special meeting in February 2025 with the express purpose of removing Mr. Clement as a Manager. At that meeting, EFTI voted to remove Mr. Clement. Further, both the minutes of the February 2025 Special Meeting and the June 2025 Resolution were signed by Mr. Edwards on behalf of EFTI. Therefore, there are two documents containing the “express written consent” of the “Member holding the Majority Interest” to Mr. Clement’s removal as a Manager as required by Section 5.4 of the Operating Agreement. Based on this evidence, the district court could reasonably conclude EFTI and Cowboy Racing were likely to succeed on the merits of their claim that Mr. Clement had been lawfully removed as a Manager.
[¶22] Despite any purported finality in the phrasing of the district court’s order, this is a preliminary ruling that applies only to the Appellees’ request for a preliminary injunction. It is not a decision on the merits of Appellees’ declaratory judgment claim. The parties may present additional evidence regarding the propriety of Mr. Clement’s removal and any alternative interpretations of the Operating Agreement at the trial on the merits. See Brown, 2021 WY 83, ¶ 12, 491 P.3d at 1027.
CONCLUSION
[¶23] The district court did not abuse its discretion when it granted the preliminary injunction. Appellees established they were likely to succeed on the merits of their claim regarding the lawfulness of Mr. Clement’s removal as a Manager of Cowboy Racing. Although the district court incorrectly phrased its preliminary injunction order as a final conclusion on the interpretation of the Operating Agreement when there had been no consolidation as allowed by W.R.C.P. 65(a)(2), the parties may present additional evidence regarding the lawfulness of Mr. Clement’s removal and any alternative interpretations of the Operating Agreement at the trial on the merits. Affirmed.
Section 5.11. EFTI held a special meeting in February 2025 with the express purpose of removing Mr. Clement as a Manager, as required by Section 5.11 At that meeting EFTI voted to remove Mr. Clement due to his “unilateral authorization” of attorney’s fees that had not been approved by any other member. This evidence provides this Court an alternative reason to affirm the district court’s decision. See, e.g., Blair v. State, 2022 WY 121, ¶ 22, 517 P.3d 597, 602 (Wyo. 2022) (stating the Court “can affirm an evidentiary ruling ‘on any legal ground appearing in the record’”).