United States v. Medoff

• Court: Court of Appeals for the First Circuit
• Decided: November 18, 2025
• Docket: 24-1750
• Status: Published

Opinion

United States Court of Appeals For the First Circuit

No. 24-1750

UNITED STATES OF AMERICA,

Appellee,

v.

CRAIG MEDOFF,

Defendant, Appellant.

APPEAL FROM THE UNITED STATES DISTRICT COURT FOR THE DISTRICT OF MASSACHUSETTS

[Hon. Mark L. Wolf, U.S. District Judge]

Before

Montecalvo, Howard, and Aframe, Circuit Judges.

Amy Barsky, with whom Fick & Marx LLP was on brief, for appellant. Donald C. Lockhart, Assistant United States Attorney, with whom Leah B. Foley, United States Attorney, was on brief, for appellee.

November 18, 2025 AFRAME, Circuit Judge. In 2016, following approximately

four years of litigation in a civil securities fraud enforcement

action brought by the Securities and Exchange Commission ("SEC"),

defendant-appellant Craig Medoff agreed to the entry of a judgment

that, for ten years, barred him and any entity he owned or

controlled "from participating in the issuance, offer, or sale of

any security."

In 2024, Medoff pleaded guilty to criminal contempt of

this judgment, see 18 U.S.C. § 401(3); Fed. R. Crim. P. 42(a), and

was sentenced to twenty months of imprisonment, a variance of ten

months above the top of the applicable guidelines sentencing range

("GSR"). He now seeks vacatur of his sentence on two grounds. He

principally argues that the sentencing judge should have recused

himself from presiding over the criminal contempt proceeding

because his impartiality might reasonably have been questioned.

See 28 U.S.C. § 455(a). Alternatively, he contends that his

sentence was procedurally and substantively unreasonable. We

reject his arguments and affirm.

I.

Medoff has a long history of violating federal

securities laws and being involved in related criminal and civil

proceedings. We provide a detailed account of this history to

place Medoff's recusal arguments in context. The following facts

are undisputed.

- 2 - A.

On September 7, 1993, Medoff settled an SEC civil

enforcement action, brought in the Southern District of New York,

that charged him and the company of which he was president with

fraudulently offering unregistered securities. In settling the

case, Medoff consented to the entry of a permanent injunction that

barred him from violating the anti-fraud provisions of the federal

securities laws; required him to pay a civil penalty of $95,500;

and ordered him to disgorge money he had obtained through his

fraudulent conduct. On January 6, 1995, in a related

administrative action, Medoff also agreed to an offer of settlement

that barred him from associating with any securities broker,

dealer, investment advisor, investment company, or municipal

securities dealer. Medoff neither paid the civil fine nor complied

with the disgorgement order. Nor, as we shall see, did he abide

by the terms of the prohibitory orders that regulated his conduct

with respect to securities.

On April 26, 1995, in a criminal action that was also

instituted in the Southern District of New York, Medoff pleaded

guilty to a sealed information charging him with two counts of

conspiracy to commit fraud in connection with the offer and sale

of securities. On October 20, 2009, more than fourteen years after

his guilty plea, Medoff was sentenced to three years of probation

and a $6,000 fine, which he did not fully pay. From 2011 to 2014,

- 3 - Medoff was twice incarcerated for a total of about seventeen months

on probation violations for failing drug tests and not making

payments towards the fine.

B.

On December 14, 2012, while Medoff's troubles in the

Southern District of New York were ongoing, the SEC instituted a

civil enforcement action in the District of Massachusetts against

Medoff; Biochemics, Inc. ("Biochemics"); and two additional

individuals. The complaint alleged, among other things, that

Medoff had participated in a fraudulent scheme to sell Biochemics

securities to investors. It also highlighted the 1993 and 1995

judicial and regulatory orders that barred Medoff from violating

the antifraud provisions of the federal securities laws and

associating with any securities broker, dealer, investment

advisor, investment company, or municipal securities dealer. The

case was assigned to then-Chief Judge Wolf.

On March 18, 2015, the SEC submitted a proposed consent

judgment for defendant Biochemics to the district court. The

judgment contained language stating that the company would have to

pay a substantial fine and disgorgement order within fourteen days

of its entry. The court rejected this proposed judgment,

apparently because all parties agreed that Biochemics would be

unable to pay the disgorgement order and fine within the short

- 4 - time specified. The court stated that it would not issue an order

that it did not intend to enforce.

A few days later, on March 25, 2015, the district court

entered a revised judgment for defendant Biochemics that obligated

the company to disgorge $17,147,884 (including prejudgment

interest) and to pay a civil penalty of $750,000. The revised

judgment contained a schedule requiring payment of the fine within

seven months and thereafter requiring payment of the disgorgement

order, with interest, in five consecutive monthly payments.

Biochemics paid the fine but did not make any of the disgorgement

payments. During the litigation that ensued, the court repeatedly

reiterated its unwillingness to issue orders that it did not intend

to enforce.

On May 25, 2016, the district court entered a final

consent judgment against Medoff that, for a period of ten years,

prohibited him and any entity that he owned or controlled "from

participating in the issuance, offer, or sale of any security."

The judgment also ordered Medoff to pay a $100,000 civil penalty

and to disgorge $14,370.20 (including prejudgment interest). As

in the Southern District of New York litigation, Medoff did not

satisfy any of these obligations.

On September 27, 2023, the SEC sought an order for Medoff

to show cause why he should not be held in civil contempt for

failing to comply with the 2016 consent judgment. In a memorandum

- 5 - supporting its motion, the SEC stated that, in violation of the

2016 consent judgment, since at least 2021, Medoff "had involvement

with, and likely ownership and/or control of, a financial services

company . . . [named] Nova Capital International LLC" ("Nova

Capital"). The SEC attached to its memorandum affidavits and

exhibits supporting its allegations about Medoff's involvement

with Nova Capital and detailing Medoff's history of securities

fraud and non-compliance with court orders. It requested, among

other things, an order directing Medoff to cease violating the

2016 consent judgment and to disgorge all money earned through its

violation. It also requested "[a]n order imposing such other

sanctions as the Court deems appropriate, including additional

civil penalties, to ensure Medoff's future compliance."

On October 13, 2023, the district court issued a

responsive memorandum and order stating that the SEC had provided

"ample evidence to justify the initiation" of civil contempt

proceedings. The court also stated that the SEC's evidence "raises

the question of whether it would be appropriate for the court to

initiate criminal contempt proceedings instead." The court

elaborated: "In view of Medoff's proven history of violating court

orders, conducting proceedings that could only result in another

order that could be violated might be futile. Therefore, [a] civil

remedy may be inappropriate and criminal contempt proceedings may

be justified."

- 6 - In the memorandum, the district court also scheduled a

hearing for October 23, 2023, "to address whether [it] should

initiate civil or criminal contempt [proceedings] for the

violations of its May 25, 2016, [consent judgment] alleged by the

SEC . . . ." And it further ordered that a representative from

the U.S. Attorney's Office attend the hearing, as well as any

counsel Medoff retained to handle a possible criminal prosecution.

The court also stated that, if Medoff wished to have counsel

appointed from the Criminal Justice Act ("CJA") panel, he should

file an appropriate financial affidavit with the court in time for

appointed counsel to attend the hearing.

Medoff did not request the appointment of counsel -- he

instead attempted to secure private counsel -- but counsel from

the CJA panel nonetheless attended the hearing as an observer.

So, too, did an assistant U.S. attorney. At the hearing, the

district court reiterated its concern that issuing another civil

contempt order would be futile. Speaking to counsel for the SEC,

the court explained why it was considering criminal contempt:

I don't issue orders that I don't expect are going to be obeyed and my concern is . . . that if I just order [Medoff] not to . . . engage in the securities business, I don't know why I would have any confidence he's going to obey the order the third time when he, according to you, didn't obey the 2016 order at all. And if he's in the securities business, he's continuing to present a danger.

- 7 - Counsel for the SEC responded that the SEC only has the authority

to move for civil contempt, not criminal contempt; that the agency

shared the court's futility concerns; but that, in its view, a

targeted civil contempt order could nonetheless be effective.

Counsel added: "If I'm wrong, then the recourse to criminal

contempt remains."

At the end of the hearing, the district court agreed to

give Medoff additional time to secure funds to hire private

counsel. The court also deferred deciding whether to institute a

criminal contempt proceeding while the parties explored a possible

resolution of the SEC's motion to show cause. But the court made

clear that it was then inclined towards initiating criminal

contempt proceedings. The court also advised Medoff of his right

to remain silent, and that, if a criminal case were initiated

against him, he might be entitled to a jury trial; appointed

counsel; and pretrial release, if there were a combination of

conditions that would protect the community from any danger he

posed. Two days later, on October 25, 2023, two privately retained

lawyers appeared for Medoff.

On November 17, 2023, the parties filed a joint status

report notifying the district court that they had reached an

agreement to resolve the SEC's motion to show cause. The

agreement, which outlined several civil sanctions to be imposed on

Medoff, was subject to his providing the SEC with certain

- 8 - information and documentation. The joint status report also

stated: "[I]n light of Medoff's agreement to comply and supporting

documentation [sic], the SEC does not recommend sanctions beyond

those outlined above to ensure future compliance." By order dated

November 22, 2023, the court directed the parties to file a jointly

proposed order implementing their agreement and including "a

provision stating that [the agreement] is without prejudice to the

court's authority to initiate criminal contempt proceedings for

any possible violation of prior orders and/or the proposed order."

Six days later, the parties filed the proposed order.

On December 1, 2023, the district court held a hearing

on the proposed order, which contained the required language

regarding criminal contempt and also, among other things,

obligated Medoff to cease engaging in conduct violative of the

2016 consent judgment; to provide the SEC with certain information

about Nova Capital's clients; to provide Nova Capital clients with

curative notice of his "disciplinary history"; and to provide

detailed accountings of his and Nova Capital's assets and

liabilities. At the hearing, the court asked counsel for the SEC

what it meant by its statement in the November 16, 2023, status

report that it did not recommend sanctions beyond those outlined

in the report. SEC counsel replied:

I think there may have been some confusion there, and I apologize if that was unclear to the Court. What we were referring to there

- 9 - is with respect to civil contempt. So part of our original motion contemplated that there may be penalties or other sanctions entered by your Honor to enforce the 2016 judgment. This is just speaking to any further civil contempt.

At the close of the hearing, the court stated that it would issue

the proposed order and again deferred deciding whether to institute

criminal contempt proceedings until after Medoff produced the

remaining discovery contemplated by the order.

On February 5, 2024, after discovery closed, the SEC

filed a status report summarizing what it had learned from Medoff's

production of information and documents. The SEC reported, among

other things, that Medoff had produced all the information that he

was required to produce by the December 1, 2023, order; that Medoff

was in the process of producing additional documents sought by the

SEC based on what it learned in discovery; that Medoff had, since

2016, controlled Nova Capital and, through it, had engaged in the

offer and sale of securities in violation of the 2016 consent

judgment; that Medoff had used the alias "Alexander Carlin" in

connection with his Nova Capital work; that Nova Capital had

received approximately $1.8 million in fees in violation of the

2016 consent judgment; that Medoff's personal net benefit from the

$1.8 million in fees was worth approximately $1.675 million; that

the SEC subsequently would be moving for a final order of civil

contempt; and that the SEC would be seeking, among other things,

- 10 - that Medoff disgorge the money that he obtained from violating the

2016 consent judgment.

On February 6, 2024, the district court responded with

an order stating that the SEC's February 5, 2024, status report

"suggests that promptly initiating criminal contempt proceedings

for [Medoff's alleged violations of the 2016 consent judgment] may

be most appropriate for several reasons, including but not limited

to the risk that an order of disgorgement if Medoff is held in

civil contempt may be futile." Therefore, the court directed the

SEC to file a memorandum and affidavit addressing whether Medoff

had the ability to pay $1.675 million, or any other substantial

sum, if ordered to do so. The court also invited, but did not

require, Medoff to do the same.

The next day, the SEC filed the required memorandum and

affidavit. These documents represented that Medoff had received

approximately $200,000 annually for work he performed through Nova

Capital from June 2016 through November 2023; that Medoff had spent

or distributed all that money and had a negative net worth; that

Medoff was the beneficiary of a family trust with approximately

$920,000 in liquid assets; that the trust presently paid Medoff

approximately $2,200 per month; that the SEC did not include the

trust assets in assessing Medoff's net worth because Medoff did

not possess or exercise control of those assets; and that Medoff

had informed the SEC that he had a possible opportunity for future

- 11 - non-securities-related income that he could use to pay down a

monetary penalty.

The day after the SEC's filing, Medoff filed his own

affidavit, which stated that he was "deeply apologetic to the Court

[for failing] to comply with the 2016 [consent judgment]." The

affidavit also stated that Medoff had paid $10,000 toward the

disgorgement and civil penalties owed from that judgment; that he

did not have a "current ability to pay a substantial disgorgement

or civil penalty" but was "in the process of arranging three

separate revenue streams that, if successful, [would] enable [him]

to pay the disgorgement penalties over time"; and that, going

forward, he was willing to pay the SEC twenty percent of his

quarterly income from the trust and other sources.

On February 9, 2024, the district court convened another

hearing on whether it should institute criminal contempt

proceedings against Medoff. At that hearing, counsel for the SEC

confirmed its earlier representation that the SEC does not have

the authority to seek criminal contempt. In doing so, SEC counsel

acknowledged that, on a couple of occasions, the SEC had "weighed

in" with a U.S. attorney's office about that office initiating a

criminal contempt proceeding but had been told that the office

could not act without a court order. SEC counsel also represented

that the SEC believed that Medoff had a negative net worth of

approximately $200,000; that he lacked any assets to pay the fine

- 12 - imposed in the 2016 consent judgment or any order of disgorgement;

but that he was no longer engaging in conduct prohibited by the

Medoff's counsel opposed the initiation of criminal

contempt proceedings by emphasizing that Medoff had been

cooperative with the SEC over the preceding several months.

Medoff's counsel also reiterated statements in his client's

affidavit that Medoff would apportion twenty percent of his

personal income to pay down his debt and that Medoff had some

potential income streams that he could earn consonant with the

2016 consent judgment. Medoff's counsel concluded by stating: "I

think we've demonstrated Mr. Medoff's intent to cooperate

and . . . just ask . . . for a little bit more time to prove it."

The district court next heard from Medoff himself, who

attributed his violation of the 2016 consent judgment to

"confusion" because he was an "active drug addict" when the

judgment was entered. The court asked Medoff when he had stopped

using drugs, and Medoff responded "[t]hree years ago, Your Honor."

The court followed up by asking whether, during the three years

since he stopped using drugs, Medoff had continued to work on

behalf of Nova Capital using an alias. Medoff confirmed that he

had. The court then announced its intention to issue a written

order requiring Medoff to show cause why he should not be held in

criminal contempt. No party objected to the court initiating

- 13 - criminal contempt proceedings without referral to the U.S.

Attorney's Office for evaluation and, if appropriate, a grand jury

indictment.

On February 12, 2024, the district court issued the

contemplated order. The order invoked section 401(3) of title 18,

which, in pertinent part, empowers a court to punish contempt of

its authority through "[d]isobedience or resistance to its lawful

writ, process, order, rule, decree, or command." The order also

invoked Federal Rule of Criminal Procedure ("Rule") 42(a)(1),

which provides that a person prosecuted for criminal contempt shall

receive notice from the court of the time and place of trial,

reasonable time to prepare a defense, a statement of the essential

facts constituting the charged criminal contempt, and a

description of it as such. The order charged Medoff with

"knowingly and willfully violating . . . the 2016 [consent

judgment] by engaging in the alleged offer and sale of securities

by his conduct related to Nova Capital International LLC."

Pursuant to Rule 42(a)(2), the district court appointed

the U.S. Attorney for the District of Massachusetts to prosecute

the case.1 The court also set the trial for April 1, 2024, and,

1 By its terms, Rule 42(a)(2) obligates the court to "request" that the criminal contempt proceeding be prosecuted by an attorney for the government and contemplates a discretionary decision by the government whether to accept the request. But no party objected to the court's appointment of the government without

- 14 - pursuant to Rule 42(a)(3), released Medoff pending a hearing on

whether he should be detained pending trial. Because the court

determined that incarceration for a period of more than six months

might be necessary to serve the purposes of sentencing, it ruled

that Medoff was entitled to a jury trial. See Codispoti v.

Pennsylvania, 418 U.S. 506, 512, 516-17 (1974) (indicating that

the jury-trial right attaches to a criminal contempt charge

potentially resulting in a sentence of more than six months in

prison); Rule 42(a)(3) ("A person being prosecuted for criminal

contempt is entitled to a jury trial in any case in which federal

law so provides"). And because the alleged contempt did not

involve disrespect toward or criticism of the court personally,

the court stated that it would preside in the contempt proceeding.

See Rule 42(a)(3) ("If the criminal contempt involves disrespect

toward or criticism of a judge, that judge is disqualified from

presiding at the contempt trial or hearing unless the defendant

consents.").

In its order, the district court further elaborated on

why it had chosen to initiate a criminal contempt proceeding. The

court started by observing that civil and criminal contempt

proceedings serve different purposes. See United States v.

such a request or, as we shall describe, to the government's tacit acceptance of the appointment by timely entering an appearance and subsequently prosecuting the case.

- 15 - Marquado, 149 F.3d 36, 39 (1st Cir. 1998). It explained that

sanctions for civil contempt are meant to coerce compliance with

court orders, while sanctions for criminal contempt are meant to

punish violations of, and to deter future violations, of such

orders. See id. at 39–40; Yates v. United States, 355 U.S. 66, 75

(1957). After acknowledging that a court should resort to criminal

sanctions only after determining, for good reason, that civil

sanctions would be insufficient, the court identified two reasons

for charging Medoff with criminal contempt. See Shillitani v.

United States, 384 U.S. 364, 371 n.9 (1966).

First, the district court stated that "holding Medoff in

civil contempt would be futile" because Medoff lacked the means to

pay an appropriate penalty or disgorgement order, and because

Medoff's history of flouting court orders even after serving jail

time suggested that fear of prison would not deter him from

disobeying a civil contempt order.2 Second, the court stated:

[T]here is far more than probable cause to believe that Medoff knowingly, willfully, and repeatedly disobeyed the 2016 [consent judgment]. There is, therefore, reason to be concerned that Medoff may continue to present a danger of committing crimes and that his incarceration may be necessary to protect the public. In any event, it is important to the

2 Despite its concerns about futility, the court authorized the SEC to continue exploring the possibility of disgorgement and other civil sanctions pursuant to its motion to show cause in the civil action. But the court also stated that it "intend[ed] to resolve the criminal charge before conducting civil contempt proceedings." The civil action remains ongoing.

- 16 - administration of justice to demonstrate that court orders cannot be violated with impunity. If proven, or admitted, a criminal sanction for contempt will be justified to punish Medoff, to protect the public, and to deter him and others from engaging in comparable conduct in the future. See Yates, 355 U.S. at 74.

C.

We now reach the criminal contempt proceedings that give

rise to this appeal. The case began with a flurry of pretrial

activity. On February 12, 2024, the district court issued a

pretrial order reiterating that trial would commence on April 1,

2024; directing the parties to confer and report by February 20,

2024, whether they had either reached an agreement to resolve the

case or would like a continuance until February 27, 2024, to

attempt to do so; and setting deadlines for various pretrial

disclosures.

On February 21, 2024, the district court issued an order

permitting Medoff's counsel in the 2016 civil enforcement action

to withdraw, granting Medoff's request for the appointment of CJA

counsel (which was supported by the required financial affidavit),

and appointing Attorney Peter Horstmann to serve as CJA counsel.

On February 22, 2024, Assistant U.S. Attorney {"AUSA") Leslie

Wright appeared for the government. Again, as we have mentioned,

at no point did the government indicate an unwillingness to accept

the court's appointment to prosecute the case. Cf. Fed R. Crim.

- 17 - P. 42(a)(2) ("The court must request that the contempt be prosecuted

by an attorney for the government, unless the interest of justice

requires the appointment of another attorney. If the government

declines the request, the court must appoint another attorney to

prosecute the contempt.").

Five days after his appointment, Attorney Horstmann

filed an assented-to motion to extend the relevant deadlines and

continue the trial. The motion stated that Attorney Horstmann

needed more time to prepare and had other trials scheduled to begin

on April 1, 2024, and June 17, 2024. The motion also stated that

AUSA Wright had a trial scheduled to start on July 15, 2024. The

motion requested that trial be continued to an unspecified,

mutually convenient date. The next day, on February 27, 2024, the

parties filed a joint status report requesting additional time to

confer about potentially resolving the case.

On February 28, 2024, a magistrate judge ordered Medoff

released on conditions pending trial. The conditions did not

include drug testing or drug treatment. The day following Medoff's

release, the district court issued an order granting the

assented-to motion to extend deadlines and continue the trial; it

also extended until March 12, 2024, the parties' deadline to report

whether they had reached an agreement to resolve the case. This

order did not set a new trial date.

- 18 - On March 12, 2024, the parties filed a joint status

report stating that they did not anticipate resolving the case and

that a trial would last one or two days. The report also stated

that Medoff would file discovery motions and might request the

district court to recuse itself and to dismiss the criminal

contempt proceeding based on collateral and/or judicial estoppel.

On March 14, 2024, the district court filed a responsive

order asking Attorney Horstmann to report whether he still expected

his trial scheduled for April 1, 2024, to begin on that date. The

order further directed Medoff to file any recusal motion by March

20, 2024. It also ordered Medoff to include with any such motion

a memorandum addressing (1) why disqualification was warranted

considering that the alleged criminal contempt did not involve

disrespect or criticism of the court, see Fed. R. Crim. P.

42(a)(3); and (2) if the motion to recuse were to be based in whole

or in part on section 455(a) of title 28, which requires the court

to recuse where the court's "impartiality might reasonably be

questioned," to discuss the legal standards for applying the

statute. Finally, the order stated that trial would begin on April

22, 2024, if the court were to deny any motion to recuse.

On March 20, 2024, Medoff filed two motions: a motion to

recuse under section 455(a) and an assented-to motion to continue

the trial date from April 22, 2024, to an unspecified, mutually

convenient date. The recusal motion argued that the following

- 19 - rulings and conduct gave rise to an appearance of bias that would

cause a reasonable observer to question the district court's

impartiality: (1) the court had shown a "fixation" with initiating

criminal contempt proceedings by repeatedly mentioning its

likelihood of doing so in the months following the filing of the

SEC's motion to show cause; (2) the court had raised the

possibility of charging Medoff with criminal contempt without the

SEC requesting that it do so; (3) the court had rushed the

proceedings by initially scheduling a trial date for just more

than six weeks after their initiation; (4) the court had expressed

an unfounded concern, based on Medoff's prior conduct, that he

constituted a "danger" to the community and was a candidate for

pretrial detention; and (5) the court had sandbagged Medoff by

initiating the criminal case after leading Medoff to believe that

he could avoid criminal liability by cooperating with the SEC to

resolve the motion to show cause.3

3 Medoff later raised this sandbagging argument in an April 18, 2024, motion captioned "Motion in Limine to Dismiss Criminal Case or to Suppress Involuntary Statements Induced by Promissory Estoppel." In an April 23, 2024, memorandum and order, the district court denied the motion, noting that, in affording Medoff the opportunity to resolve the SEC's motion to show cause, the court had repeatedly advised him that it was doing so "without prejudice to its right to institute criminal contempt proceedings." Medoff does not challenge this ruling or otherwise raise sandbagging as a concern on appeal. Therefore, we will say nothing more on the issue.

- 20 - On March 25, 2024, the district court entered a

memorandum and order denying the assented-to motion to continue

the trial. The order stated: "Both the motion for a lengthy

continuance of the trial date and Medoff's motion to recuse suggest

that [Medoff's] counsel . . . may not understand the elements of

criminal contempt." The order directed the parties' counsel to

file by March 28, 2024, affidavits stating whether they had

reviewed all the pleadings, hearing and deposition transcripts,

and documents produced to the SEC since the filing of the SEC's

motion to show cause. By way of explanation, the court stated:

"The information is necessary for the court to make a properly

informed decision on whether any further continuance of the trial

date is justified." The parties' counsel timely complied.

Meanwhile, on March 26, 2024, the government filed a

response to Medoff's recusal motion under section 455(a). The

response stated:

[I]n an abundance of caution -- and because the Court has itself referred this matter to the government for prosecution -- the government defers to the Court as to whether, in the unique circumstances in which a court has sua sponte initiated criminal contempt proceedings, the various defense contentions in this case meet the "high threshold . . . required to satisfy" the [section] 455(a) recusal standard . . . based on the need to avoid the "objective appearance" of partiality.

- 21 - (ellipses in original) (quoting Liteky v. United States, 510 U.S.

540, 558 (1994) (Kennedy, J., concurring)). On appeal, the

government remains neutral on the recusal question and accordingly

has declined to respond to Medoff's argument in this Court.

On April 9, 2024, the district court convened a hearing

on Medoff's motion to recuse. At the outset, the court expressed

displeasure that the U.S. Attorney's Office had taken no position

on the motion and doubt that it intended to properly prosecute the

criminal contempt case. After hearing from Medoff's counsel, the

court denied the motion. In doing so, the court reiterated its

reasons for initiating a criminal contempt action, recited the

applicable legal standards, and rejected the specific arguments

made in Medoff's motion. The court emphasized that, in its view,

there was no basis for a reasonable person to question its

impartiality.

In particular, the district court stated (1) that what

Medoff described as its "fixation" on the likelihood of a criminal

contempt proceeding was better understood as its effort to protect

Medoff's rights and to allow him to make informed decisions about

whether and how to cooperate in the civil case; (2) that the SEC's

failure to recommend criminal contempt was meaningless because, as

the agency explained, it lacked the authority to do so; (3) that

the initially contemplated April 1, 2024, trial date was

appropriate given the uncontested facts, the months of warnings

- 22 - that the court had given about the likelihood of criminal contempt

proceedings, and then-counsel's knowledge of the case;4 and (4)

that the statement regarding Medoff's possible pretrial detention

was nothing more than a statement of what the law requires when a

court initiates a criminal contempt proceeding, see 18

U.S.C. § 3142; Fed. R. Crim. P. 42(a)(3), 46.

The district court concluded the hearing by stating that

Medoff's motion to recuse "appears . . . frivolous" and "to be an

effort to . . . further delay the trial." The court added: "It

is, in my view . . . an effort to manipulate the system for

strategic purposes, perhaps to obtain another judge who would have

to do a great deal of work to prepare and, as I say . . . to

further delay this matter." Medoff's counsel responded: "I would

just like to say that there's no judge shopping going on here.

There's absolutely none. . . . I'm not shopping for a better

judge." The court replied: "Okay, maybe for delay . . . ." To

which Medoff's counsel responded: "Maybe. Maybe righteous delay."

The court then delayed the trial date for another week, to April

29, 2024.5

4 On February 12, 2024, the date on which the district court set April 1, 2024, as the trial date, counsel in the civil action had not yet withdrawn. As noted above, Attorney Horstmann was not appointed CJA counsel until February 21, 2024. 5 On April 23, 2024, Medoff filed a notice of appeal of the district court's April 9, 2024, order denying his motion to recuse. Perhaps recognizing that this interlocutory order was not

- 23 - On April 16, 2024, Medoff filed an assented-to

"emergency" motion for a hearing on a proposed Rule 11(c)(1)(C)

plea agreement. The motion sought an expedited hearing because of

the impending trial date and filing deadlines. This binding plea

agreement, if accepted, would have required the district court to

sentence Medoff to zero to three months in prison followed by

twelve months of supervised release.

The following day, the district court issued a written

memorandum and order denying the motion and rejecting the plea

agreement. The court explained that, based on its understanding

of Medoff's criminal history, a zero-to-three-month sentence would

involve a downward variance, as the applicable GSR called for a

sentence of four to ten months. But, in the court's view, there

were likely no justifiable reasons for such a downward variance.

See U.S.S.G. § 6B1.2(c)(2) (stating that a court may accept a

Rule 11(c)(1)(C) plea requiring a sentence outside the applicable

guideline sentencing range only if "(A) the agreed sentence is

outside the applicable guideline range for justifiable reasons;

and (B) those reasons are set forth with specificity in the

statement of reasons form"). In reaching this conclusion, the

subject to immediate appeal, see 28 U.S.C. § 1292, Medoff subsequently withdrew the notice, and, on May 8, 2024, filed a petition for a writ of mandamus in this Court. The petition sought, inter alia, the district court's recusal. About a week later, we denied Medoff's petition.

- 24 - court noted that, given its prior ruling that Medoff had a

jury-trial right because a six-month sentence might not be

sufficient to serve the interests of sentencing, the parties should

have foreseen that the court would reject a plea agreement

requiring the imposition of a sentence of not more than three

months. And the court also opined that, considering the case's

travel, the proposed plea agreement may have been submitted for

purposes of delay.

On April 23, 2024, citing medical reasons, the district

court rescheduled a pretrial conference (previously scheduled for

April 26, 2024) to April 29, 2024, and rescheduled the trial to

May 20, 2024. On April 26, 2024, the court issued a memorandum

and order directing that Medoff attend the pretrial conference and

that the parties be prepared to address whether Medoff's conditions

of release should be amended to include drug testing and, if

appropriate, drug treatment. The court explained that it was

raising the issue because Medoff's appearance and conduct at the

April 9, 2024, hearing on the recusal motion had caused it concern

that Medoff once again was using illegal drugs.

Meanwhile, also on April 26, 2024, the parties filed a

joint motion for leave to file a motion for a hearing on a second

proposed Rule 11(c)(1)(C) plea agreement. This time the proposed

plea agreement would have bound the court to impose a sentence in

the four-to-ten months range, followed by thirty-six months of

- 25 - supervised release, and carried with it a government

recommendation for a four-month sentence.

At the April 29, 2024, pretrial conference, the district

court denied the motion for a hearing on the second proposed plea

agreement and rejected the agreement. In doing so, the court

questioned whether the voluminous filings that the government was

forced to prepare and submit in getting ready for trial following

the rejection of the first proposed plea agreement should lead

Medoff to lose the two-level downward adjustment for acceptance of

responsibility that the parties had agreed to in predicting the

applicable GSR. See U.S.S.G. § 3E1.1, cmt. n.1(H) (stating that

"the timeliness of the defendant's conduct in manifesting the

acceptance of responsibility" should be accounted for in

evaluating whether to give a downward adjustment). If Medoff were

not given this adjustment, his GSR would be eight to fourteen

months, and the government's recommended sentence of four months

would involve a downward variance for which there might not be

justifiable reasons. The court also expressed concern that

Medoff's criminal history -- which included unscored criminal

history -- might under-represent the risk that he would engage in

future criminal conduct. If this were so, the court indicated, it

might be inclined to give an above-guidelines sentence.

court also addressed Medoff's release conditions. The court

- 26 - explained that it had become concerned that Medoff might be using

drugs again because, at the April 9, 2024, hearing, Medoff had

placed his head on the table for a long period of time, knocked

over a glass of water, and was then permitted to leave the

courthouse, at counsel's request, before the hearing concluded.

Medoff's counsel advised the district court that Medoff

was ill at the April 9, 2024, hearing and argued against imposing

additional release conditions. At one point during his counsel's

argument, and against the advice of counsel (who repeatedly urged

Medoff to remain silent), Medoff interrupted to advise the court

that he is "a documented freebase cocaine addict"; that his drug

of choice "is freebase cocaine, not heroin, not opiates, not

anything that would make [him] sleepy"; that he had a severe chest

cold at the earlier hearing; and that if he had been using cocaine,

he would have been frenetic and not lethargic.

After hearing argument and Medoff's comments, the

district court ordered that drug testing and, if appropriate, drug

counseling be incorporated into Medoff's release conditions. The

court also ordered an immediate drug test to set a baseline. The

test indicated Medoff's use of marijuana and cocaine. Afterwards,

Medoff admitted to having consumed marijuana edibles that morning.

The court did not revoke Medoff's pretrial release, but it warned

him that he faced a substantial risk of revocation if he were to

test positive again.

- 27 - Finally, the district court concluded the April 29,

2024, pretrial conference by questioning whether it had been

appropriate to appoint CJA counsel for Medoff. The court expressed

concern about Medoff's representation of indigency and failure to

make any fine or disgorgement payments given that he was the

beneficiary of a trust holding more than $900,000 for his benefit

and had received more than $1.6 million for conduct that violated

the 2016 consent judgment.

On May 14, 2024, the probation department filed a

petition to issue a summons for Medoff to appear because he had

tested positive for cocaine use on three additional occasions

following his initial positive test. The following day, Medoff

filed a motion to enter a guilty plea, without any agreement with

the government. See Fed. R. Crim. P. 11(a)(1). On May 16, 2024,

the district court convened a hearing to address these filings.

At the hearing, Medoff admitted that he had violated the 2016

consent judgment and pleaded guilty to the charge of criminal

contempt. The court accepted Medoff's plea and scheduled

sentencing for August 7, 2024. The court also again raised

questions about the accuracy and completeness of the financial

statement that Medoff had filed in support of his request for CJA

counsel and placed a gag order on Medoff to preclude him from

communicating with one Mark Levy, a person to whom Medoff allegedly

owed money and who the court suspected of hiding assets for Medoff.

- 28 - In addition, the district court continued Medoff's

release on conditions prior to sentencing. The court said it was

a close question whether to order that Medoff be taken into custody

and stated that it was not sure whether it was correct to find by

clear and convincing evidence, as it did, that Medoff was unlikely

to flee or to pose a danger to the safety of any other person.6

The court did, however, impose several additional conditions on

Medoff's release. In any event, on May 31, 2024, after additional

drug tests showed continued cocaine use, and after Medoff sent the

probation department an email making clear that he had been

dishonest about his drug use, the department again petitioned the

court to issue a summons for Medoff to appear. On June 3, 2024,

following a hearing on the petition, the court revoked Medoff's

supervised release.

On August 5, 2024, after reading the presentence report

("PSR") prepared by the probation department for Medoff's

sentencing, the district court issued a memorandum and order

directing the parties to be prepared to discuss at sentencing

several issues bearing on whether it should impose a variant

sentence above the applicable GSR, which the PSR set at four to

ten months in prison. In particular, the court intended to explore

6 The record contains evidence of unscored criminal conduct involving violent and threatening behavior by Medoff over the years.

- 29 - whether Medoff should be entitled to a two-level reduction for

acceptance of responsibility (as the PSR recommended with the joint

agreement of the parties), notwithstanding that he had repeatedly

lied to the court and the probation department about his drug use;

whether Medoff's criminal history category of II substantially

understated the seriousness of his criminal history and the

likelihood that he would commit future crimes; and whether it

should attach significance to the fact that, although Medoff was

not shown to have caused any victim to suffer a loss, he had

nonetheless received approximately $1.675 million for violating

the 2016 consent judgment and had never paid the fine or

disgorgement ordered in that judgment. The court indicated that

it was considering an upward variant sentence of thirty months.

On August 7, 2024, the district court conducted Medoff's

sentencing hearing. Despite its previous reservations, the court

agreed to award Medoff a two-level reduction for acceptance of

responsibility, citing his cooperation with the SEC after it filed

its motion to show cause and stating that it would instead consider

Medoff's lying in the context of deciding whether to impose an

upward variance. This led the court to agree with the PSR that

Medoff's total offense level was eight; his criminal history

category was II; his GSR was four to ten months in prison followed

by twenty-four to sixty months of supervised release; and his fine

- 30 - range was $2,000 to $20,000 (with a maximum of $250,000) plus a

$100 special assessment.

The district court then invited counsel to speak.

Counsel for the SEC took no position on what sentence should be

imposed but stated that the injunctive relief that Medoff flouted

"is one of the tools that the SEC uses to achieve its aim of

protecting investors." Government counsel recommended a sentence

of ten months -- the high end of the GSR. In doing so, government

counsel expressed agreement with the court that civil contempt

would have been an insufficient remedy. Government counsel also

explained that, because this was not a case that the government

investigated or charged, the government's understanding of the

facts evolved considerably as the case proceeded. As a result,

and as the government learned more about Medoff's behavior and

history, its sentencing recommendations grew more severe.

Government counsel did not express opposition to a variance above

the GSR and agreed with the court's suggestion that the case

involved aggravating factors not accounted for by the GSR.

Medoff's counsel argued for a time-served sentence,

which would have amounted to about three months in prison.

Medoff's counsel emphasized that his conduct had not caused anyone

harm and was fueled by a now-controlled drug addiction. Medoff's

counsel also contended that Medoff's violation of the 2016 consent

- 31 - judgment was not in and of itself dangerous to any purchaser of

securities.

Ultimately, the district court imposed an upward

variance and sentenced Medoff to twenty months in prison and

thirty-six months of supervised release. The court also imposed a

$20,000 fine, to be paid starting immediately, and a $100 special

assessment.

In imposing this sentence, the district court stated

that it had considered a sentence of thirty months but decided

that twenty months was sufficient and not more than necessary to

serve the purposes of sentencing. See 18 U.S.C. § 3553(a) (setting

forth the factors to be considered in imposing a sentence). The

court observed that, even after crediting Medoff's cooperation

with the SEC as a mitigating factor, an upward variance was

warranted because a criminal history category of II substantially

underrepresented both the seriousness of Medoff's criminal

history -- which included a considerable amount of uncharged and

unscored criminal conduct -- and the likelihood that he would

commit future crimes. The court also explicitly discussed each of

the section 3553(a) sentencing criteria to explain how they

required the court to account for several aggravating factors that

militated in favor of an above-guidelines sentence. Medoff raised

no objections to the court's sentencing analysis when afforded an

opportunity to do so.

- 32 - II.

As we noted at the outset, Medoff presents two arguments

on appeal. Primarily, he contends that the district court erred

in denying his motion to recuse. Alternatively, he asserts that

his sentence should be vacated because it was both procedurally

and substantively unreasonable. We begin with recusal.

A.

Medoff's challenge to the district court's denial of his

motion to recuse proceeds along two lines. The first contests the

lawfulness of the district court's decision to initiate a criminal

proceeding on its own rather than referring the case to the U.S.

Attorney's Office for evaluation and, if appropriate, indictment

by a grand jury. The second focuses on the court's rulings and

comments following the SEC's filing of its motion to show cause in

the civil case and argues that, when viewed collectively by a

reasonable observer, the observer would conclude that the court's

actions gave rise to an appearance of "partiality" requiring

recusal under section 455(a).

Medoff has waived his first argument for recusal. As

previously noted, Medoff never suggested below that the district

court lacked the authority to initiate a criminal contempt

proceeding absent a prior referral to the U.S. Attorney's Office

for evaluation and, if appropriate, a grand jury indictment. Nor

does Medoff argue on appeal that the court plainly erred in

- 33 - proceeding as it did. We therefore decline to take up Medoff's

first line of argument and confine our analysis to Medoff's

argument that the court's rulings and comments required recusal

under section 455(a) because of an appearance of partiality. See,

e.g., United States v. Feleciano-Candelario, 128 F.4th 5, 16 (1st

Cir. 2025) (failure to argue that an unpreserved issue involved

plain error waives any claim for relief based on that issue).7

The showing that Medoff must make to prevail on this

argument is formidable. Again, section 455(a) requires that a

judge "disqualify himself in any proceeding in which his

impartiality might reasonably be questioned." Therefore, a judge

7 Two members of the United States Supreme Court have suggested, in the related but not identical context where a trial court appointed prosecutors under Rule 42(a)(2) after the government declined its request to prosecute, that a trial court's decision to prosecute anyway, without executive branch approval, may raise separation of powers concerns and violate a defendant's due process rights. See Donziger v. United States, 143 S. Ct. 868, 869-70 (2023) (Gorsuch, J., joined by Kavanaugh, J., dissenting from the denial of a writ of certiorari) ("By interpreting Rule 42 as authorizing courts to make their own decision to initiate a prosecution -- and even to override a contrary decision by the Executive Branch -- the [decision below] not only arrogated a power to the Judiciary that belongs elsewhere. It allowed the district court to assume the 'dual position as accuser and decisionmaker' -- a combination that violates the due process rights of the accused." (quoting Williams v. Pennsylvania, 579 U.S. 1, 9 (2016))); see also Young v. United States ex. rel. Vuitton et Fils, S.A., 481 U.S. 787, 815-25 (1987) (Scalia, J., concurring in the judgment) (arguing in a case involving court-appointed, private prosecutors that the Article III judicial power does not permit federal judges to seek out violators of court orders in order to punish them). For the reasons stated, we do not engage this complex and unsettled issue.

- 34 - considering a motion to recuse must ask whether "the facts asserted

'provide what an objective, knowledgeable member of the public

would find to be a reasonable basis for doubting the judge's

impartiality.'" In re Boston's Children First, 244 F.3d 164, 167

(1st Cir. 2001 (quoting In re United States, 666 F.2d 690, 695

(1st Cir. 1981)). It is true, as Medoff notes, that "doubts

ordinarily ought to be resolved in favor of recusal." In re United

States, 441 F.3d 44, 56 (1st Cir. 2006) (quoting In re United

States, 158 F.3d 26, 30 (1st Cir. 1998)). But the Supreme Court

has provided guidance, which we summarize immediately below, on

what does and does not give rise to objectively reasonable doubts

about a judge's partiality. Medoff's brief does not mention, let

alone endeavor to apply, this guidance.

As a threshold matter, as the Supreme Court explained in

Liteky, "judicial rulings alone almost never constitute a valid

basis for a bias or partiality motion." 510 U.S. at 555. "Almost

invariably, [such rulings] are proper grounds for appeal, not for

recusal." Id. Moreover, a judge's opinions that are, as here,

premised on "facts introduced or events occurring in the course of

the current proceedings, or of prior proceedings," and not on a

source outside of judicial proceedings (known as an "extrajudicial

source"), "do not constitute a basis for a bias or partiality

motion unless they display a deep-seated favoritism or antagonism

that would make fair judgment impossible." Id.; see id. at 558

- 35 - (Kennedy, J., concurring in the judgment)

("[U]nder [section] 455(a), a judge should be disqualified only if

it appears that he or she harbors an aversion, hostility[,] or

disposition of a kind that a fair-minded person could not set aside

when judging the dispute."); see also Caperton v. A.T. Massey Coal

Co., 556 U.S. 868, 889 (2009) (quoting Liteky, 510 U.S. at 558

(Kennedy, J., concurring in the judgment)). Consequently,

judicial remarks "that are critical or disapproving of, or even

hostile to, counsel, the parties, or their cases, ordinarily do

not support a [section 455(a)] bias or partiality challenge."

Liteky, 510 U.S. at 555.8

8 In Liteky, the Supreme Court provided the following extensive explanation for the demanding showing one must make to establish a judge's partiality. We quote in its entirety because of its relevance to our evaluation of Medoff's recusal argument: Not all unfavorable disposition towards an individual (or his case) is properly described by [the words "bias" or "prejudice," which constitute the elements of section 455(a) partiality, see id. at 552]. One would not say, for example, that world opinion is biased or prejudiced against Adolf Hitler. The words connote a favorable or unfavorable disposition or opinion that is somehow wrongful or inappropriate, either because it is undeserved, or because it rests upon knowledge that the subject ought not to possess (for example, a criminal juror who has been biased or prejudiced by receipt of inadmissible evidence concerning the defendant's prior criminal activities), or because it is excessive in degree (for example, a criminal juror who is so inflamed by properly admitted evidence of a defendant's prior criminal activities

- 36 - Moreover, whether a judge's impartiality might

reasonably be questioned is a determination ultimately committed

to the discretion of the district court. In re United States, 666

F.2d at 695. Given that reasonable minds may differ on this

matter, we review a court's decision not to recuse under the highly

deferential abuse-of-discretion standard. See United States v.

Torres-Estrada, 817 F.3d 376, 380 (1st Cir. 2016). In applying

that he will vote guilty regardless of the facts). . . . The judge who presides at a trial may, upon completion of the evidence, be exceedingly ill disposed towards the defendant, who has been shown to be a thoroughly reprehensible person. But the judge is not thereby recusable for bias or prejudice, since his knowledge and the opinion it produced were properly and necessarily acquired in the course of the proceedings, and are indeed sometimes (as in a bench trial) necessary to completion of the judge's task. As Judge Jerome Frank pithily put it: "Impartiality is not gullibility. Disinterestedness does not mean child-like innocence. If the judge did not form judgments of the actors in those court-house dramas called trials, he could never render decisions." Also not subject to deprecatory characterization as "bias" or "prejudice" are opinions held by judges as a result of what they learned in earlier proceedings. It has long been regarded as normal and proper for a judge to sit in the same case upon its remand, and to sit in successive trials involving the same defendant. . . . "Partiality" [within the meaning of section 455(a)] does not refer to all favoritism, but only to such as is, for some reason, wrongful or inappropriate. Liteky, 510 U.S. at 550-52 (explaining why a finding of partiality ordinarily must be premised on an "extrajudicial source") (citation omitted) (emphasis in original).

- 37 - this standard, we "will sustain the district court's ruling unless

we find that it cannot be defended as a rational conclusion

supported by a reasonable reading of the record." Id. (alteration

omitted) (quoting United States v. Pulido, 566 F.3d 52, 62 (1st

Cir.2009)).9

When evaluated against the substantive law and our

standard of review, Medoff's argument for recusal is unconvincing.

Medoff advances nine reasons why the district court abused its

discretion in denying his recusal motion. Medoff says, first,

that the district court exhibited partiality by initiating a

criminal contempt proceeding even though the government had not

done so and even though the SEC took the position that such a

proceeding was unnecessary. But any suggestion that the

government's failure to initiate a criminal contempt proceeding

reflected disagreement with the court about the propriety of such

a proceeding is belied by its acceptance, without objection, of

9 We have at times described the applicable appellate standard of review as asking whether an "objective, reasonable member of the public, 'fully informed of all the relevant facts,' would fairly question the trial judge's impartiality." In re United States, 441 F.3d at 56-57 (quoting In re United States, 158 F.3d at 31). This formulation should not be understood to require reversal if a single, objectively reasonable person could fairly question a judge's impartiality. Rather, consistent with how abuse-of-discretion review operates, the denial of a recusal motion will be upheld if, as we have just stated, reasonable minds may differ about the judge's ruling.

- 38 - the court's appointment to prosecute Medoff, and its subsequent

prosecution of him. Cf. Fed. R. Crim. P. 42(a)(2) (expressly

contemplating government denial of a court's request to prosecute

a criminal contempt).10

Moreover, Medoff misreads the record in twice suggesting

that the SEC opined that a criminal contempt proceeding was

unnecessary. As we have noted, the SEC counsel disclaimed any

authority to initiate a criminal contempt proceeding. SEC counsel

also clarified that, in stating that further sanctions were

unnecessary in the November 23, 2023, joint status report, the

agency intended only to say that it regarded further civil

sanctions as unnecessary. The agency never expressed a view on

the district court's conclusion that a criminal contempt

proceeding was appropriate.

Medoff next contends that the district court's status as

"the party aggrieved" by Medoff's violation of its 2016 consent

10 In his reply brief, Medoff states that the government "express[ed] the view that criminal contempt was not warranted." Medoff also states that the district court "dismiss[ed] the government's view of recusal," implying that the government tacitly agreed with him that recusal was appropriate. Neither statement is supported by the record. As to the former statement, the record contains no "express" indication from the government that a criminal contempt prosecution was unwarranted. Indeed, as we have just noted, the government's acceptance of the court's appointment and subsequent prosecution of the case would seem, if anything, to reflect a contrary view. As to the latter statement, we have no basis to disregard the government's statement that it had no position on Medoff's motion. There was thus no "government view" of the recusal issue for the district court to dismiss.

- 39 - judgment rendered it insufficiently detached to maintain

impartiality. In support of the argument, Medoff points to the

court's repeated statements that it does not issue orders that it

does not intend to enforce; its description of Medoff's recusal

motion as "frivolous"; its chastisement of the government for not

opposing Medoff's motion; and its related concern that the

government would not properly prosecute the case.

We note preliminarily that the frustration expressed in

these statements was directed at counsel for their conduct in the

civil and criminal cases, and not at Medoff himself. Moreover, as

we have noted, Medoff does not argue, let alone demonstrate, that

there is reason for treating these statements as outside the rule

that "remarks during the course of a trial that are critical or

disapproving of, or even hostile to, counsel, the parties, or their

cases, ordinarily do not support a bias or partiality challenge."

Liteky, 510 U.S. at 555; see also United States v. Caramadre, 807

F.3d 359, 374-75 (1st Cir. 2015) (concluding that judge's actions

"did not cross the Liteky line" though judge, inter alia,

characterized party's motion as "entirely meritless, bordering on

frivolous" and "an incredibly cynical and disturbing effort to

manipulate the court and the criminal justice system").

Medoff's third ground supporting recusal highlights the

speed with which the district court sought to hold the criminal

contempt trial and the court's repeated expressions of concern

- 40 - that Medoff's counsel was attempting to unduly delay it. Medoff

notes that the court set a trial date fewer than forty-five days

from the date on which it instituted the criminal proceeding and

states: "When defense counsel objected and requested a

continuance -- with the government's assent -- the district court

denied the request." This argument again misstates the record.

As we have explained, on February 29, 2024, the court granted newly

appointed Attorney Horstmann's February 26, 2024, motion to

continue the trial date. Subsequently, after setting trial for

April 22, 2024, and initially denying Medoff's motion to continue

trial further, the court continued the trial date twice more: to

April 29, 2024, and then to May 20, 2024. Medoff's remedy for

these case-management "judicial rulings" was "appeal,

not . . . recusal." Liteky, 510 U.S. at 555.11

The remaining grounds that Medoff asserts in support of

his motion for recusal stem from events and comments that

post-dated the motion's filing and resolution. Medoff would have

us infer partiality from the district court's rejections of the

two proposed Rule 11(c)(1)(C) plea agreements; doubts the court

expressed about Medoff's entitlement to credit for acceptance of

11 To the extent that Medoff seeks to have us infer partiality from the district court's repeated assertions that counsel was attempting to unduly delay the trial, we note that counsel acknowledged to the court that Medoff's recusal motion was "maybe" motivated, at least in part, by a "righteous" desire for delay.

- 41 - responsibility before awarding the credit and the adequacy of

Medoff's criminal history score, given his unscored criminal

history; concerns the court expressed about whether Medoff's

punishment should be enhanced because of his dishonesty with the

court and the probation department about his drug use; concerns

the court expressed about Medoff's dangerousness, given his

history of violating securities laws and court orders; and concerns

the court expressed about whether Medoff was hiding assets to avoid

paying prior fines and disgorgement orders and to secure

court-appointed counsel.

Because these grounds post-dated the filing and

disposition of Medoff's motion to recuse, they were, of course,

not considered by the district court. Thus, they cannot themselves

directly ground a ruling that the court abused its discretion in

denying the motion. Yet even assuming their relevance to the

court's state of mind during the criminal case, they do not affect

our judgment. Medoff treats the wrongfulness of these actions and

comments as largely self-evident. See Liteky, 510 U.S. at 552

(explaining that that a judge's predisposition towards a litigant

must be "wrongful or inappropriate" to constitute partiality

within the meaning of section 455(a)). But in our view, these

actions and comments, whether they are considered individually or

in combination, do not suggest a wrongful predisposition against

Medoff, which (again) the Supreme Court has defined as a

- 42 - "deep-seated . . . antagonism" on the part of the court "that

would make fair judgment impossible." Liteky, 510 U.S. at 555.

The record, which we have described in detail,

demonstrates that the district court regarded Medoff's extensive

history of flouting judicial orders as requiring a serious and

prompt response for which additional civil sanctions would be

inadequate. It also reveals a court troubled by a perceived

tendency on the part of the SEC to enter into unenforceable

settlement agreements and, consequently, committed to ensuring the

enforceability of the orders it issued. Neither view strikes us

as wrongful, inappropriate, or partial. Moreover, throughout the

civil and criminal proceedings, the court advised Medoff of, and

respected, his rights. Indeed, much of the court's commentary

offered transparency to the parties about the court's thinking,

which provided useful information on how the parties might go about

resolving the case. In sum, this case does not involve the "rarest

[of] circumstances" where a court shows "the degree of favoritism

or antagonism required" for recusal under section 455(a) "when no

extrajudicial source is involved." Liteky, 510 U.S. at 555. We

therefore conclude that the district court acted within its

discretion in denying Medoff's motion to recuse.

Medoff alternatively argues that the twenty-month

upwardly variant sentence that the district court imposed was both

- 43 - procedurally and substantively unreasonable.12 As to procedure,

Medoff contends that the court made two mistakes: (1) the court

erred in concluding that an upwardly variant sentence was necessary

to deter Medoff from engaging in additional criminal conduct and

to protect the public from further crimes; and (2) the court erred

in "entirely dismissing" national sentencing statistics indicating

that three months was the average sentence for defendants sentenced

under the same guideline and GSR, and in the same criminal history

category, as Medoff. As to substance, Medoff contends that his

twenty-month sentence was longer than necessary when viewed in the

light of various record data points. The government defends the

lawfulness of the sentence, arguing that Medoff has waived his

procedural objections and that, in any event, the sentence was

procedurally and substantively reasonable. Medoff denies waiver

of his procedural reasonableness arguments.

1.

We bypass the issue-preservation dispute because, even

assuming Medoff's procedural reasonableness arguments are properly

before us, they reveal no abuse of discretion. See United States

v. Waithe, 150 F.4th 16, 23 (1st Cir. 2025) (bypassing a dispute

12 Medoff has completed the custodial portion of his sentence. His sentencing claim nevertheless remains a live controversy because, if successful, he could seek an equitable reduction in his supervised-release term. See United States v. Reyes-Barreto, 24 F.4th 82, 86 (1st Cir. 2022).

- 44 - over whether a procedural reasonableness challenge was preserved

where review of the issue, if preserved, would be for abuse of

discretion and where there was no such abuse). Medoff's first

procedural reasonableness argument is that his sentence cannot be

justified under the rationales of deterring "criminal conduct," or

protecting the public from "further crimes," 18

U.S.C. § 3553(a)(2)(B),(C), because his violation of the 2016

civil consent judgment was not itself "criminal conduct" and

because he does not otherwise have a recent criminal conviction.

Medoff's argument proceeds from a faulty premise. Violating the

terms of an injunction in circumstances amounting to criminal

contempt of that injunction is itself a crime -- one to which

Medoff pleaded guilty. See 18 U.S.C. § 401(3). The court did not

commit procedural error in treating the factors specified in sub-

sections 3553(a)(2)(B), (C) as relevant to Medoff's sentence.

Medoff's second procedural reasonableness argument also

proceeds from a faulty premise. The district court did not

"entirely dismiss" the sentencing statistics to which Medoff

refers. Rather, after acknowledging the statutory obligation to

avoid unwarranted sentence disparities, id., § 3553(a)(6), and

after explicitly recognizing that the average sentence for

defendants with the same guidelines scores as Medoff was three

months, the court stated:

- 45 - But every case is unique. I don't know anything about those cases [referenced in the statistics]. I don't know if they're criminal contempt cases, I don't know anything about the history and characteristics of the people, but I doubt that many, if any, have a combination of factors that make this an exceptional case, including decades of flagrantly violating court orders, in some instances federal security laws.

The court did not fail to consider the sentencing statistics; it

justifiably disagreed with Medoff's view of their importance. Here

too there was no abuse of discretion. See Waithe, 150 F.4th at

25.

2.

Medoff's substantive reasonableness argument is that his

twenty-month sentence was longer than necessary and therefore an

abuse of discretion. See id., 150 F.4th at 25 (reviewing for abuse

of discretion a preserved challenge to the substantive

reasonableness of a sentence). This argument is premised on two

underlying assertions. The first is that the district court

erroneously regarded him as a serial violator of federal securities

laws when he had only a single, decades-old criminal conviction

that was accounted for in his GSR and for which he was sentenced

to only probation and a fine. The second is that his twenty-month

sentence was incommensurate when evaluated in light of five

different record data points: (1) the sentences proposed in the

two Rule 11(c)(1)(C) plea deals (zero-to-three months and

- 46 - four-to-ten months) that the court rejected; (2) the applicable

GSR (four-to-ten months); (3) the government's recommended

sentence (ten months); (4) the sentencing statistics showing the

average sentence of defendants with Medoff's guidelines scores

(three months); and (5) the time Medoff served for two probation

violations in connection with the 1995 securities fraud

conviction.13

Medoff's first underlying argument is without merit.

Although the civil actions that the SEC brought against Medoff in

1993 and 2012 did not culminate in criminal convictions, they too

involved admitted "violations" of federal securities laws as that

term is commonly understood. The district court therefore did not

err in regarding them as such. Moreover, we have reviewed the

record with care and see no evidence that the court was unaware

either that the 1995 criminal conviction was accounted for by the

GSR or that Medoff's prior incarcerations were not, at least

directly, for violations of federal securities laws.

In emphasizing the five data points on which his second

underlying argument rests, Medoff does little to engage the

district court's discussion of the section 3553(a) criteria and

why they, in its view, revealed several aggravating factors not

13 Medoff alleges that he served a total of twelve months for these probation violations, and the court appears to have proceeded on the same assumption. The PSR indicates, however, that Medoff served just over seventeen months.

- 47 - accounted for in the GSR and necessitating an upward variance.

These factors included that Medoff had been flouting court orders

"going back to the 1990s [that] restrict[ed] [his] participation

in the securities industry"; that Medoff was convicted on two

counts of security fraud in 1995, then served significant time for

probation violations related to these convictions, but that his

time in prison did not deter him from violating the 2016 consent

judgment; that Medoff had received approximately $1,675,000 for

conduct violative of the 2016 consent judgment, but that these

monies obtained from criminal conduct were not accounted for in

calculating his GSR; that Medoff began violating the 2016 consent

judgment almost immediately after it was entered; that Medoff's

criminal contempt of the 2016 consent judgment involved seven years

of criminal conduct; that Medoff used a false identity to conceal

this criminal conduct; that Medoff repeatedly violated the

conditions of his pretrial release in the criminal case by using

drugs and then lying to the court and probation office about having

done so; that Medoff and others like him need to be deterred from

violating court orders; and that Medoff was a danger to the public,

given his persistent involvement in securities work

notwithstanding multiple court orders barring him from doing so.

"Where, as here, the [sentencing] court imposes an

upwardly variant sentence, it must explain its reasons for doing

so." Waithe, 150 F.4th at 25 (quoting United States v.

- 48 - Flores-Nater, 62 F.4th 652, 655 (1st Cir. 2023)). Moreover, "[t]he

court's burden of explanation 'increases in proportion to the

extent of [its] deviation from the [GSR].'" Id. (quoting United

States v. Montero-Montero, 817 F.3d 35, 37 (1st Cir. 2016)). But

there is no single correct sentence in any case; rather, there is

"a universe of reasonable sentencing outcomes." United States v.

Clogston, 662 F.3d 588, 592 (1st Cir. 2011). And a sentence falls

within that universe if the sentencing court provides a "plausible

sentencing rationale and a defensible result." Flores-Nater, 62

F.4th at 655 (quoting United States v. Díaz-Lugo, 963 F.3d 145,

157 (1st Cir. 2020)).

Here, the district court's thorough explanation of the

aggravating factors that led it to impose an upwardly variant

twenty-month sentence was quite plausible and more than sufficed

to establish the sentence's defensibility. We therefore reject

Medoff's argument that his sentence was substantively

unreasonable. In so ruling, we reiterate that, although the

government recommended a sentence of ten months, it ultimately

agreed with the court that there were aggravating factors not

accounted for by the GSR and expressed no opposition to the

upwardly variant sentence that the court imposed.

III.

For the reasons stated, we affirm defendant-appellant

Craig Medoff's sentence.

- 49 -