Judge‑Initiated Criminal Contempt and the High Bar for Recusal Under § 455(a): United States v. Medoff (1st Cir. 2025)

I. Introduction

United States v. Medoff, No. 24‑1750 (1st Cir. Nov. 18, 2025), is a significant First Circuit decision at the intersection of three sensitive areas:

• a district judge’s power to initiate criminal contempt proceedings to enforce his own orders under 18 U.S.C. § 401(3) and Fed. R. Crim. P. 42;
• the standards for judicial recusal under 28 U.S.C. § 455(a) when the same judge both issued the underlying civil injunction and then initiates criminal contempt of that injunction; and
• the scope of sentencing discretion, including substantial upward variances, in criminal contempt cases arising out of repeated violations of securities‑law injunctions.

The case arises from a long history of securities‑related misconduct by defendant‑appellant Craig Medoff, including a 1990s SEC case in the Southern District of New York, a related criminal fraud conviction, and, most centrally, a 2016 SEC civil enforcement action in the District of Massachusetts. In that 2016 case, Medoff consented to a ten‑year injunction forbidding him and any entities he owned or controlled from participating in the issuance, offer, or sale of any security. He never paid the ordered penalties and disgorgement—and, according to later findings, he proceeded to flout the injunction almost immediately and for years, using an alias while running a financial services firm, Nova Capital International LLC.

When the SEC moved in 2023 for civil contempt of the 2016 judgment, the presiding judge (Judge Mark L. Wolf, who had also overseen the civil case) concluded that further civil remedies might be futile and instead initiated criminal contempt proceedings sua sponte under Rule 42, appointing the U.S. Attorney’s Office to prosecute. Medoff eventually pled guilty. The district court determined a Guidelines Sentencing Range (GSR) of 4–10 months but imposed a 20‑month term of imprisonment—an upward variance of 10 months—plus a $20,000 fine and three years of supervised release.

On appeal, Medoff pressed two claims:

1. Recusal: He argued that Judge Wolf should have recused himself from the criminal contempt case under 28 U.S.C. § 455(a) because his impartiality might reasonably be questioned, in light of the judge’s role in initiating the criminal case, his comments during the SEC civil proceedings, his handling of scheduling and pleas, and his strong views about enforcing his own orders.
2. Sentencing: He argued that the 20‑month sentence was both procedurally and substantively unreasonable.

The First Circuit (Judge Aframe, joined by Judges Montecalvo and Howard) affirmed in full. The opinion does several important things:

• It holds that merely because a judge initiates criminal contempt proceedings to enforce his own prior injunction, and manages those proceedings firmly, does not create a reasonable appearance of partiality requiring recusal under § 455(a).
• It clarifies that appellate review of § 455(a) rulings remains highly deferential: the “objective observer” test is applied within an abuse‑of‑discretion framework, not de novo.
• It underscores that criminal contempt of an injunction is itself “criminal conduct” for purposes of deterrence and public‑protection considerations under 18 U.S.C. § 3553(a)(2).
• It affirms a significant upward variance in a criminal contempt sentence based on a long pattern of defiance of court orders, extensive unscored criminal behavior, and dishonesty while on pretrial release.
• It pointedly avoids, on grounds of waiver, the broader structural question (raised in Donziger) whether judge‑initiated contempt prosecutions without Executive Branch agreement raise separation‑of‑powers or due process concerns.

II. Summary of the Opinion

A. Factual and Procedural Background

1. Medoff’s prior securities history

The opinion recounts an extensive, nearly three‑decade saga:

• 1993 SEC case (S.D.N.Y.): Medoff and his company settled fraud charges related to the offer of unregistered securities. He agreed to a permanent injunction against violating antifraud provisions, a civil penalty, and disgorgement—but never paid.
• 1995 SEC administrative sanctions: He accepted an associational bar from the securities industry (brokers, dealers, advisers, etc.).
• 1995 criminal case (S.D.N.Y.): He pled guilty to two conspiracies to commit securities fraud. Remarkably, he was not sentenced until 2009: three years’ probation and a $6,000 fine, which he again did not fully pay, and he spent about 17 months incarcerated between 2011–2014 for probation violations.

2. The 2012–2016 SEC/Biochemics case in Massachusetts

In 2012, the SEC brought a civil enforcement action in the District of Massachusetts (assigned to then‑Chief Judge Wolf) against Medoff, Biochemics, and others for a fraudulent scheme involving Biochemics securities. This complaint flagged the 1993 and 1995 orders and bars.

In that case:

• Biochemics consent judgment (2015): Judge Wolf rejected a first draft order that required rapid payment of a huge disgorgement sum that all parties knew Biochemics could not pay, remarking that he does not issue orders he does not intend to enforce. A revised order imposed a schedule; Biochemics paid the civil penalty but not disgorgement.
• 2016 Medoff consent judgment: On May 25, 2016, the court entered a final consent judgment against Medoff:
  • ten‑year bar on him and any entity he owned or controlled “from participating in the issuance, offer, or sale of any security”;
  • $100,000 civil penalty plus disgorgement with prejudgment interest.
  He paid none of it.

3. The 2023 SEC civil contempt motion

In September 2023, the SEC moved for an order to show cause why Medoff should not be held in civil contempt of the 2016 judgment for his involvement with Nova Capital International LLC, a financial services company he apparently owned/controlled, through which he had engaged in the offer and sale of securities since at least 2021. The SEC sought coercive relief, including disgorgement of earnings from the violation and additional civil penalties.

Judge Wolf responded with an October 13, 2023 memorandum:

• He found “ample evidence” to justify civil contempt proceedings.
• But he also questioned whether criminal contempt proceedings might be more appropriate, given Medoff’s history of violating orders and non‑payment: another civil order might be “futile.”
• He set a hearing to consider whether to pursue civil contempt, criminal contempt, or both, and ordered the presence of the U.S. Attorney’s Office and potential criminal defense counsel.

Over the next several months:

• The SEC emphasized it could seek only civil contempt, though it shared concerns about futility; it also noted that in practice U.S. Attorneys would not prosecute contempt without a court order.
• The court repeatedly advised Medoff of his potential criminal exposure and rights (jury trial, counsel, pretrial release standards).
• The parties negotiated a civil resolution of the SEC’s motion, culminating in a December 1, 2023 order requiring, among other things, cessation of prohibited conduct, disclosures to Nova Capital clients, and detailed asset/accounting disclosures. Importantly, the order and the court’s directions were expressly “without prejudice” to the court’s authority to initiate criminal contempt proceedings based on past violations.

4. Discovery reveals extensive violations; court initiates criminal contempt

By early February 2024, after robust discovery under the December order, the SEC reported:

• Medoff had controlled Nova Capital since 2016 and engaged in the offer and sale of securities in clear violation of the 2016 bar;
• Nova Capital had received roughly $1.8 million in fees, of which Medoff’s net benefit was estimated at $1.675 million;
• He had used an alias (“Alexander Carlin”) to conceal his involvement;
• He had essentially no net worth but was beneficiary of a $920,000 family trust that paid him monthly income;
• The SEC would seek civil contempt and disgorgement, but Medoff’s ability to pay was doubtful.

On February 6, 2024, the court issued an order stating that this record suggested criminal contempt might be “most appropriate,” mainly because further disgorgement in civil contempt could again be futile. He ordered submissions on Medoff’s ability to pay. After reviewing those, and after a February 9 hearing at which Medoff admitted long‑term drug use and ongoing Nova Capital work under an alias, the judge announced he would initiate criminal contempt.

On February 12, 2024, the court:

• served Rule 42(a)(1) notice of prosecution for criminal contempt under 18 U.S.C. § 401(3), charging that Medoff “knowingly and willfully” violated the 2016 judgment by participating in the offer and sale of securities through Nova Capital;
• set trial for April 1, 2024;
• determined that potential incarceration exceeding six months meant Medoff was entitled to a jury trial (citing Codispoti v. Pennsylvania);
• appointed the U.S. Attorney to prosecute under Rule 42(a)(2);
• explained that criminal contempt, unlike civil contempt, is punitive and intended to protect the public and the courts’ authority, and that criminal sanctions should be used when civil remedies are inadequate (citing Shillitani, Yates, and Marquado).

5. Pretrial proceedings, recusal motion, and plea negotiations

Medoff received appointed counsel (CJA) and the U.S. Attorney’s Office accepted appointment, filing an appearance without objecting to prosecution.

The case then saw rapid litigation:

• The initial April 1 trial date was continued at defense request; subsequent dates were reset multiple times; trial was eventually set for May 20, 2024.
• A March 12 joint status report signaled that Medoff might move to recuse the judge and to dismiss on estoppel grounds.
• On March 20, Medoff filed a motion for recusal under 28 U.S.C. § 455(a), and a motion to continue the trial.

The recusal motion argued that a reasonable observer would doubt the judge’s impartiality based on:

1. the judge’s repeated references to likely criminal contempt;
2. raising criminal contempt sua sponte when the SEC had sought only civil sanctions;
3. initially scheduling trial only weeks after initiating contempt;
4. suggesting Medoff might be a “danger” to the community and a candidate for detention;
5. alleged “sandbagging” by initiating criminal proceedings after encouraging cooperation in the SEC’s civil contempt process.

The government filed a neutral response on recusal, taking “no position” and “deferring to the Court.”

On April 9, 2024, the judge held a hearing and orally denied recusal, explaining why the asserted grounds did not reach the high bar for bias under Liteky. He characterized the recusal motion as “frivolous” and as an effort to delay or “judge shop,” though defense counsel disclaimed any intent to seek a different judge and candidly admitted that “maybe righteous delay” was part of the objective.

Meanwhile, the parties twice tried to resolve the case through binding plea agreements under Rule 11(c)(1)(C):

• First C plea: 0–3 months imprisonment and 12 months supervised release. The court rejected it, finding that such a downward variance from the 4–10 month GSR lacked “justifiable reasons” under U.S.S.G. § 6B1.2(c)(2), particularly given the court’s earlier conclusion that a sentence beyond 6 months might be required.
• Second C plea: a sentence within the 4–10 month range, with the government recommending 4 months and 36 months supervised release. The court also rejected this, concerned that:
  • Medoff’s post‑charge conduct (especially his late pleas and the government’s heavy trial preparation) undermined the basis for acceptance‑of‑responsibility credit;
  • without that credit, the proper GSR would be 8–14 months, making a 4‑month sentence an unjustified downward variance; and
  • Medoff’s criminal history category of II might understate his true criminal record and risk of recidivism.

6. Drug use, pretrial release violations, and guilty plea

The district court became concerned that Medoff was again using drugs after observing his behavior at an April 9 hearing. It added drug testing and possible treatment as conditions of release. A same‑day test revealed marijuana and cocaine; later tests showed additional cocaine use. Medoff admitted to recent use and to having been dishonest about it.

In May 2024, after a probation petition and further violations, he moved to plead guilty without a plea agreement. On May 16, the court accepted his guilty plea to criminal contempt, raised concerns about the accuracy of his financial affidavit (used to obtain CJA counsel) in light of the trust and Nova Capital revenues, and imposed a gag order regarding a suspected asset‑shielding associate. The court narrowly decided to continue release pending sentencing but eventually revoked release on June 3, 2024, after continued cocaine use and dishonesty.

7. Sentencing

A presentence report calculated:

• total offense level 8 (including a two‑level acceptance‑of‑responsibility reduction);
• criminal history category II;
• GSR of 4–10 months, and a fine range $2,000–$20,000.

Prior to the August 7, 2024 sentencing, the judge issued an order signaling consideration of a substantial upward variance, possibly to 30 months, based on:

• whether acceptance‑of‑responsibility credit remained appropriate given Medoff’s lies about drug use;
• whether criminal history category II materially understated his criminal record and risk of future crimes;
• the significance of the estimated $1.675 million he received for conduct that violated the 2016 injunction, combined with his failure to pay any of the fine or disgorgement.

At sentencing:

• The court, despite misgivings, granted the two‑level acceptance‑of‑responsibility reduction, in part due to his cooperation with the SEC, leaving the GSR at 4–10 months.
• SEC counsel took no position on sentence but emphasized the importance of injunctions as tools to protect investors.
• The government recommended 10 months (top of GSR), acknowledged that its recommendations had become more severe as it learned more about Medoff’s history, and did not oppose an upward variance.
• Defense counsel sought a time‑served sentence (~3 months), stressing that no investor losses were shown and framing the conduct as driven by drug addiction now under control.

The court imposed:

• 20 months’ imprisonment (a 10‑month upward variance),
• 36 months’ supervised release,
• a $20,000 fine and $100 assessment.

The court explained that it had considered a 30‑month sentence but deemed 20 months “sufficient, but not greater than necessary” under 18 U.S.C. § 3553(a). It found:

• Medoff’s criminal history category II substantially under‑represented his real record and the likelihood of future crimes, given decades of defiance and unscored criminal conduct;
• the seven years of ongoing, deliberate contempt (starting almost immediately after the 2016 order) and use of an alias were serious aggravators;
• Medoff had repeatedly lied to the court and probation regarding his drug use while on release;
• he had obtained roughly $1.675 million for conduct that was itself criminal contempt, yet none of that financial benefit was captured by the sentencing guidelines calculation;
• criminal contempt and repeated violation of securities injunctions posed a danger to the public and to the integrity of judicial orders.

B. Holdings on Appeal

1. Recusal

Medoff advanced two conceptual strands under § 455(a):

1. that a judge cannot constitutionally or fairly initiate a criminal contempt prosecution of his own orders without referral to and decision by the Executive Branch (raising separation‑of‑powers and due process concerns); and
2. that, in any event, the judge’s conduct and comments created an appearance of partiality.

The First Circuit:

• Waiver of structural/separation‑of‑powers challenge. It held that Medoff had waived any challenge to the very fact of judge‑initiated prosecution because he never objected below to the procedure (e.g., by insisting on referral to the U.S. Attorney for independent charging or grand jury indictment), and he did not argue plain error on appeal. The court therefore declined to address the unresolved constitutional / structural questions flagged in Donziger v. United States (Gorsuch, J., dissenting from denial of certiorari) and Justice Scalia’s concurrence in Young v. Vuitton.
• No abuse of discretion under § 455(a). Focusing on the “appearance of partiality” claim, the court reaffirmed the Liteky standard:
  • judicial rulings and in‑court remarks are almost never grounds for recusal;
  • opinions and attitudes formed on the basis of the litigation record (not extrajudicial sources) require “deep‑seated favoritism or antagonism that would make fair judgment impossible” to warrant recusal;
  • recusal decisions are reviewed for abuse of discretion: the appellate court will sustain the denial unless it “cannot be defended as a rational conclusion supported by a reasonable reading of the record.”

Applying these principles, the court rejected, one by one, the multiple grounds Medoff cited—court’s interest in enforcing its orders, repeated mention of potential criminal contempt, brisk scheduling, critical remarks about defense delay or government neutrality, rejection of plea deals, concerns about drug use and dangerousness, and doubts about financial eligibility for CJA appointment—as normal case management and sentencing considerations, not wrongful bias. The opinion concludes that the case does not present the “rarest circumstances” where, without any extrajudicial source, judicial conduct manifests the sort of entrenched antagonism required by Liteky.

2. Sentencing

The court treats Medoff’s sentencing challenge as twofold:

• Procedural reasonableness: whether the court improperly treated his conduct as “criminal” for purposes of deterrence/public‑protection factors in § 3553(a)(2)(B)–(C), and whether it “entirely dismissed” national sentencing statistics for similarly scored defendants.
• Substantive reasonableness: whether the 20‑month sentence was “greater than necessary” in light of the GSR, the plea proposals, government recommendation, sentencing statistics, and his prior custodial history.

The First Circuit held:

• Procedurally reasonable.
  • Violating an injunction in a manner that constitutes criminal contempt is itself a crime under § 401(3); the district court did not err in treating Medoff’s conduct as “criminal” for deterrence and incapacitation purposes.
  • The court did not ignore sentencing statistics. It explicitly discussed the SEC’s cited figures showing an average 3‑month sentence for defendants with the same guideline scores but reasonably concluded that Medoff’s case presented an “exceptional” set of aggravating factors. Disagreeing with the weight afforded to comparatives is not a procedural error.
• Substantively reasonable.
  • Upward variances require a “plausible sentencing rationale and a defensible result.” Here, the court provided an extensive and coherent explanation rooted in the § 3553(a) factors.
  • Key aggravators—longstanding, repeated defiance of court orders; unscored criminal behavior; the size of the financial benefit from the contempt; use of an alias; violations and deception while on pretrial release—justified placing the sentence above the GSR.
  • The fact that the government recommended 10 months and that the Guidelines and national averages were much lower did not render 20 months outside the “universe of reasonable sentencing outcomes.” The government ultimately agreed that aggravating factors were present and did not oppose an upward variance.

Accordingly, the sentence was affirmed.

III. Analysis

A. Precedents and Authorities Considered

1. Liteky v. United States and the recusal standard

The backbone of the recusal analysis is Liteky v. United States, 510 U.S. 540 (1994). The Supreme Court in Liteky clarified:

• Section 455(a) requires disqualification when a judge’s impartiality “might reasonably be questioned,” but not every negative judicial impression or strongly worded comment qualifies.
• Bias or prejudice generally must derive from an “extrajudicial source”—i.e., something outside the proceedings. When impressions are formed through case proceedings, they warrant recusal only if they reflect a “deep‑seated favoritism or antagonism that would make fair judgment impossible.”
• “Judicial rulings alone almost never constitute a valid basis for a bias or partiality motion”; they are, instead, grounds for appeal.
• Critical or hostile remarks toward counsel or parties are ordinarily insufficient unless they evince that extreme, enduring antagonism.

Medoff faithfully applies this framework. The First Circuit quotes and relies on Liteky (and Justice Kennedy’s concurrence) to reinforce that:

“[P]artiality” does not refer to all favoritism, but only to such as is, for some reason, wrongful or inappropriate.

It then characterizes Judge Wolf’s remarks—calling the recusal motion “frivolous,” criticizing the government’s neutrality, warning of delay and manipulation—as classic examples of in‑court, record‑based, case‑related observations that fall well short of Liteky’s extreme standard.

2. Caperton v. A.T. Massey Coal Co.

Caperton, 556 U.S. 868 (2009), was cited primarily to reinforce Liteky’s “deep‑seated favoritism or antagonism” standard and to underscore that constitutional recusal (under the Due Process Clause) is reserved for highly extreme circumstances (e.g., when a litigant’s massive campaign contributions raise a “serious risk of actual bias”). Medoff is far from that zone.

3. Contempt cases: Yates, Shillitani, Codispoti, Marquado

The opinion carefully distinguishes civil and criminal contempt, leaning on:

• Yates v. United States, 355 U.S. 66 (1957): emphasizing that criminal contempt is punitive and aims to vindicate the court’s authority and deter future violations.
• Shillitani v. United States, 384 U.S. 364 (1966): noting that criminal sanctions should be reserved for situations where civil sanctions are insufficient—an idea the district court expressly invoked in choosing criminal contempt after concluding civil remedies would be futile.
• Codispoti v. Pennsylvania, 418 U.S. 506 (1974): establishing that, when a criminal contempt sentence may exceed six months, the defendant is entitled to a jury trial. This drove the judge’s early determination that a jury right attached here.
• United States v. Marquado, 149 F.3d 36 (1st Cir. 1998): a First Circuit case cited for the basic civil/criminal contempt purposes and classifications.

These precedents anchor the district court’s decision to switch from prospective civil coercion to retrospective criminal punishment once the futility of civil remedies had been revealed by Medoff’s history and financial condition.

4. Donziger v. United States and Young v. Vuitton: separation of powers and private prosecutors

The First Circuit flags but does not resolve an important structural issue:

• In Young v. United States ex rel. Vuitton et Fils S.A., 481 U.S. 787 (1987), the Supreme Court condemned the use of interested private counsel to prosecute criminal contempt and, in Justice Scalia’s concurrence, questioned whether Article III permits judges to function as initiators of prosecutions at all.
• In Donziger v. United States, 143 S. Ct. 868 (2023) (Gorsuch, J., dissenting from denial of cert.), Justices Gorsuch and Kavanaugh expressed deep concern about judge‑appointed prosecutors proceeding even after the Executive declined to prosecute, characterizing that arrangement as potentially infringing separation of powers and due process by blending “accuser and decisionmaker.”

Medoff acknowledges those concerns in a footnote but explicitly does not engage them because:

• the U.S. Attorney’s Office accepted the court’s appointment without objection;
• Medoff never argued below that the judge could not initiate the case without prior Executive consent or an indictment; and
• on appeal, he did not press a plain‑error argument.

This is a significant procedural holding: even profound constitutional objections can be waived if not preserved and properly framed on appeal.

5. First Circuit recusal and sentencing cases

The opinion cites a string of First Circuit authorities for two core propositions.

a. Recusal: In re United States, Boston’s Children First, Torres‑Estrada, Caramadre

• In re Boston’s Children First, 244 F.3d 164 (1st Cir. 2001): articulates the § 455(a) standard: recusal is required when an objective, fully informed observer would find a reasonable basis to question impartiality.
• In re United States, 666 F.2d 690 (1st Cir. 1981); 441 F.3d 44 (1st Cir. 2006): emphasizes that, although doubts are “ordinarily” resolved in favor of recusal, appellate review remains deferential; recusal is entrusted to the discretion of the district court.
• United States v. Torres‑Estrada, 817 F.3d 376 (1st Cir. 2016): confirms that abuse‑of‑discretion is the applicable standard.
• United States v. Caramadre, 807 F.3d 359 (1st Cir. 2015): upheld a trial judge’s sharp criticism of a party’s motion as “entirely meritless, bordering on frivolous,” and as a manipulative tactic, as within the bounds of Liteky and not grounds for recusal—closely analogous to Judge Wolf’s “frivolous” characterization here.

Importantly, Medoff refines the earlier “objective observer” language by explicitly reminding readers that this test must be nested within abuse‑of‑discretion review: it is not enough that a hypothetical reasonable person could question impartiality; as long as the district court’s decision can be defended as rational on the record, it stands.

b. Sentencing: Waithe, Flores‑Nater, Montero‑Montero, Clogston, Díaz‑Lugo, Reyes‑Barreto

• United States v. Waithe, 150 F.4th 16 (1st Cir. 2025): clarifies that appellate courts may bypass preservation disputes when, even under the more forgiving standard, there is no abuse of discretion.
• United States v. Flores‑Nater, 62 F.4th 652 (1st Cir. 2023), and United States v. Montero‑Montero, 817 F.3d 35 (1st Cir. 2016): establish that when a court varies from the GSR, it must offer a more substantial explanation as the degree of deviation increases.
• United States v. Clogston, 662 F.3d 588 (1st Cir. 2011): articulates the concept of a “universe of reasonable sentencing outcomes,” within which any sentence supported by a plausible rationale is upheld.
• United States v. Diaz‑Lugo, 963 F.3d 145 (1st Cir. 2020): reinforces the “plausible rationale and defensible result” standard for substantive reasonableness.
• United States v. Reyes‑Barreto, 24 F.4th 82 (1st Cir. 2022): holds that an appeal is not moot even after the custodial term is completed if success could lead to reduction in supervised release—relevant because Medoff had finished his imprisonment by the time of appeal.

B. The Court’s Legal Reasoning

1. Recusal: Why judge‑initiated contempt did not require disqualification

a. Waiver of the structural challenge

Medoff’s first line of attack—that the judge could not lawfully initiate a criminal contempt prosecution (without Executive Branch initiation or a grand jury)—raises serious questions that the Supreme Court has not definitively answered. However, the First Circuit declines to reach that issue, not by resolving it, but by finding it waived.

Crucially:

• Medoff did not object when the court, rather than the SEC or U.S. Attorney, initiated contempt proceedings under Rule 42.
• He did not contest the court’s appointment of the U.S. Attorney as prosecutor.
• On appeal, he did not argue for review under plain‑error standards.

The panel invokes its own recent precedent (Feleciano‑Candelario) for the proposition that failure to meaningfully raise an unpreserved issue as plain error waives it altogether. This is a strong reminder that even sophisticated structural issues must be preserved and properly framed—or they are lost.

b. The § 455(a) “appearance of partiality” analysis

Turning to the second, preserved argument, the First Circuit applies § 455(a) as interpreted in Liteky and its own precedents.

The key analytic steps are:

1. Source of alleged bias. All the allegedly biased behaviors arose from the judge’s management of the civil and criminal proceedings themselves—comments about futility of civil remedies, interest in criminal contempt, skepticism about plea deals, concerns about drug use and dangerousness, etc. None derived from extrajudicial information. Under Liteky, such case‑based views are presumptively legitimate unless they reflect deep‑seated antagonism.
2. Abuse‑of‑discretion overlay. The panel emphasizes that recusal determinations belong primarily to the district judge. As long as the denial of recusal “can be defended as a rational conclusion supported by a reasonable reading of the record,” it must be upheld, even if another judge might have chosen to recuse.
3. Characterization of the judge’s conduct. The court reframes many of the points that Medoff labeled as “fixation” or bias as:
   • consistent concern about enforcing court orders and the futility of civil sanctions;
   • careful efforts to protect Medoff’s rights by giving early notice of potential criminal exposure and his right to counsel, silence, and a jury;
   • ordinary case‑management decisions about scheduling and continuances;
   • strong but not improper language criticizing what the judge saw as strategic delay and an unfounded recusal motion;
   • legitimate concern for public safety and future crimes, given a documented pattern of securities violations and unscored violent behavior;
   • appropriate scrutiny of drug use and honesty during pretrial supervision; and
   • reasonable questions about CJA eligibility where the defendant enjoyed trust‑fund benefits and had generated substantial unlawful income.
4. No “deep‑seated antagonism.” Viewed as a whole, the court finds that Judge Wolf’s remarks and decisions do not reveal an animus that would make fair judgment impossible. Rather, they show a judge deeply troubled by a decades‑long pattern of defiance and a perceived institutional issue (SEC willingness to stipulate to unenforceable consent judgments), but still acting within normal judicial functions.

The panel also notes that:

• the judge repeatedly sought to inform all parties of his thinking, giving transparency rather than hiding the ball;
• the SEC’s failure to “recommend” criminal contempt was legally irrelevant, given that the agency itself admitted it lacked authority to seek criminal contempt in the first place;
• the government’s neutrality on recusal does not imply it believed the judge was biased; it simply took no position.

On this record, the court concludes the case does not present “the rarest circumstances” requiring recusal in the absence of an extrajudicial source of bias.

2. Sentencing: Procedural and substantive reasonableness

a. Procedural reasonableness

A sentence is procedurally unreasonable if, for example, the judge:

• relies on clearly erroneous factual findings;
• miscalculates the Guidelines;
• fails to consider the § 3553(a) factors; or
• fails to address non‑frivolous arguments or relevant data.

Medoff argued two procedural errors:

1. treating his conduct as “criminal conduct” for deterrence and public protection purposes under § 3553(a)(2)(B)–(C); and
2. “entirely dismissing” the nationwide statistics about similarly scored defendants.

The First Circuit rejects both.

• Criminal conduct. Criminal contempt under § 401(3) is a crime. Violating the injunction “knowingly and willfully” in a manner that warranted criminal contempt was itself criminal. There was no legal error in invoking deterrence and public‑safety rationales on that basis. The argument appears to confuse the civil nature of the original SEC case with the criminal nature of the contempt proceeding.
• Sentencing statistics. The court notes that Judge Wolf:
  • explicitly acknowledged the need to avoid unwarranted disparities under § 3553(a)(6);
  • recognized that the average sentence for defendants with similar Guidelines scores was three months; yet
  • reasonably discounted the probative weight of anonymous aggregate data because he did not know whether those other cases involved criminal contempt, comparable histories, unscored conduct, deception on release, or massive financial gain from contemptuous conduct.
  This is not refusal to consider the data; it is a reasoned decision that the data are not determinative in an atypical case.

b. Substantive reasonableness

Substantive reasonableness asks whether the sentence, viewed holistically in light of the § 3553(a) factors, is “greater than necessary” and whether it lies outside the permissible range of choices, not simply whether the appellate court might have chosen differently.

Medoff contended the 20‑month sentence was too harsh when measured against:

• the two rejected C pleas (0–3 months, and 4–10 months);
• the GSR (4–10 months);
• the government’s top‑of‑range recommendation (10 months);
• the three‑month national average for similarly scored defendants; and
• the twelve‑plus months he had earlier served on probation violations.

The First Circuit emphasizes that none of these datapoints is binding. The Guidelines and statistics are advisory; plea agreements had been rejected; and prior prison time for different violations does not preclude a harsher sentence where new conduct and history justify it. What matters is whether the district court’s rationale was plausible and the sentence defensible.

The panel endorses the district court’s explanation, highlighting:

• Magnitude and duration of contempt: Seven years of deliberate, knowing violation of a clear injunction; starting almost immediately after entry.
• Financial benefit from contempt: Roughly $1.675 million gained through prohibited securities activity, none of which was reflected in the offense level calculation.
• Pattern of defiance: A multi‑decade history of ignoring SEC orders, criminal sanctions, disgorgement orders, and fines.
• Use of deception: Use of an alias to conceal Nova Capital activities; lying to the court and probation about ongoing drug use while on pretrial release.
• Unscored criminal history: Evidence of violent and threatening conduct that did not factor into the Guidelines criminal history score but bore directly on recidivism risk and dangerousness.
• Need for deterrence and respect for law: Specific deterrence of Medoff and general deterrence of other litigants who might otherwise treat injunctions as empty words.

The court’s explicit consideration of every § 3553(a) factor, coupled with a reasoned explanation for deviating from the GSR and from statistical norms, easily satisfies the “plausible rationale and defensible result” standard.

C. Impact and Significance

1. Recusal doctrine in judge‑initiated contempt cases

Medoff is particularly important for clarifying how § 455(a) applies when:

• the same judge presides over an underlying civil enforcement action and later initiates and tries a criminal contempt prosecution for violating his own injunction; and
• the judge is vocal about his intent to enforce his orders and skeptical of the efficacy of civil remedies.

The opinion sends several clear signals:

• There is no per se rule requiring recusal simply because a judge initiates contempt proceedings to vindicate his own prior orders (so long as the contempt does not involve personal disrespect or criticism, in which case Rule 42(a)(3) requires reassignment absent consent).
• Being the “aggrieved party” in the sense of having one’s order violated does not inherently create an appearance of bias, so long as the judge’s interest is institutional—enforcing court authority and protecting the public—not personal.
• Firm judicial language about enforceability, skepticism about party strategies, and impatience with perceived delay, when grounded in the case record, are not enough for § 455(a) absent demonstrable deep‑seated antagonism.
• District judges retain broad discretion to decide recusal motions, and appellate courts will not second‑guess those decisions absent clearly unreasonable conclusions.

For defense counsel, this means recusal claims in contempt cases will face a very high bar, and motions that resemble mere disagreement with robust case management or sentencing outlooks risk being labeled “frivolous” and strategic.

2. Preservation of structural challenges to criminal contempt

Medoff also has a strong, if indirect, message about the importance of preservation and framing:

• The opinion explicitly references Justice Gorsuch’s concerns in Donziger and Justice Scalia’s in Young, acknowledging that there may be serious constitutional questions when judges initiate or drive prosecutions.
• But by finding those arguments waived due to lack of objection and the absence of a plain‑error argument, the court signals that even fundamental structural challenges must be:
  • raised in the district court when the judge initiates contempt or appoints prosecutors; and
  • preserved on appeal in the proper doctrinal terms (e.g., as plain error if unpreserved).

In practical terms, parties who wish to challenge judge‑initiated contempt prosecutions on separation‑of‑powers or due process grounds must object early and clearly, or risk forfeiting that argument in the First Circuit.

3. SEC enforcement and the turn to criminal contempt

The case is also notable as a warning in the securities‑law context:

• Consent judgments and injunctions—especially industry bars and activity bans—are not mere paper promises. Systematic violations may attract criminal contempt exposure with meaningful prison time.
• Where a defendant has a history of ignoring civil remedies, a court may conclude, consistent with Shillitani, that civil contempt would be futile and that criminal contempt is appropriate to punish past disobedience and deter future misconduct.
• Even if the SEC itself can seek only civil contempt, the district court can, on its own initiative, transform the matter into a criminal contempt case under Rule 42.

This has implications for how defendants bargain in SEC cases:

• Defendants may face significant criminal exposure down the line if they disregard consent injunctions, even years later.
• Cooperating with civil regulators and complying with orders is not just a regulatory obligation but a practical necessity to avoid future criminal contempt charges.

4. Sentencing practice in contempt and injunction‑violation cases

On sentencing, Medoff underscores several themes:

• Contempt as serious crime: Criminal contempt of a prior injunction is treated as serious “criminal conduct,” not a technicality. Long‑term, knowing violations with significant financial benefit can justify substantial prison time, even when there is no evidence of direct victim monetary loss.
• Upward variances for unscored behavior: Courts may find guideline criminal history categories inadequate where there is substantial unscored misconduct (e.g., earlier violent or threatening behavior) and may respond with upward variances rather than formal departures.
• Impact of pretrial misconduct: Lying to the court and probation, and violating release conditions (such as drug use), may not eliminate acceptance‑of‑responsibility credit in every case, but they can meaningfully support an upward variance and a harsher view of the defendant’s character and risk.
• Limited influence of averages: National sentencing statistics and guideline norms are important but not mechanically controlling. In a highly atypical case, a judge may reasonably conclude that those comparators say little about what is “sufficient, but not greater than necessary.”
• Plea deals are advisory to the court, not binding, absent acceptance: The rejection of two C‑plea arrangements here highlights that the court must independently assess whether a proposed sentence is consistent with § 3553(a) and the Guidelines’ policy statements (such as U.S.S.G. § 6B1.2).

IV. Key Legal Concepts Explained

1. Civil vs. Criminal Contempt

Both civil and criminal contempt involve disobedience of court orders, but they have distinct purposes and procedural frameworks:

• Civil contempt: Coercive or remedial.
  • Aim: To compel compliance with a court order or to compensate a party injured by non‑compliance.
  • Duration: Often conditional—contemnor “carries the keys of his prison in his own pocket” (e.g., jailed until he complies).
  • Procedures: May be more flexible; not necessarily entitled to a jury; sanctions can be lifted upon compliance.
• Criminal contempt: Punitive.
  • Aim: To punish past disobedience and vindicate the court’s authority.
  • Duration: Fixed sentence, not contingent on subsequent compliance.
  • Procedures: Treated like a crime—notice, right to counsel, proof beyond a reasonable doubt, and often the right to a jury trial (especially if potential punishment exceeds six months).

In Medoff, the district court concluded that civil contempt (further monetary orders, coercive fines, etc.) would be ineffective given Medoff’s track record and finances, and thus opted for criminal contempt to punish and deter.

2. Fed. R. Crim. P. 42 and court‑initiated contempt

Rule 42 governs criminal contempt:

• Rule 42(a)(1): The court must provide written notice of the contempt charge—time and place of trial, essential facts, and description of contempt as criminal.
• Rule 42(a)(2): The court must “request” an attorney for the government to prosecute, unless the interests of justice require appointing someone else; if the government declines, another attorney must be appointed.
• Rule 42(a)(3): The defendant is entitled to a jury trial where federal law so provides (e.g., when a sentence >6 months is possible); a judge is disqualified if the contempt involved disrespect toward or criticism of that judge, unless the defendant consents.

In Medoff, the judge:

• issued the notice himself, thereby initiating the contempt prosecution;
• appointed (effectively “requested”) the U.S. Attorney’s Office, which accepted the appointment and prosecuted;
• concluded that a sentence beyond six months might be necessary and thus ensured Medoff’s jury‑trial rights.

3. Judicial recusal under 28 U.S.C. § 455(a)

Section 455(a) requires a federal judge to disqualify himself:

in any proceeding in which his impartiality might reasonably be questioned.

Key points:

• The test is objective: Would a reasonable, well‑informed observer doubt the judge’s impartiality?
• However, the judge’s decision is reviewed for abuse of discretion. The question on appeal is not “What would we decide de novo?” but “Is the trial judge’s decision a rational reading of the record?”
• Under Liteky, case‑related comments and rulings rarely suffice unless they show “deep‑seated favoritism or antagonism” making fair judgment impossible.
• Critical remarks, expressed impatience, strong words about perceived manipulation or frivolous motions, and enforcement‑oriented attitudes generally do not require recusal if grounded in the case record.

In Medoff, all asserted grounds for recusal were case‑based; none stemmed from extrajudicial bias. The court therefore applied the demanding Liteky standard and found no abuse of discretion in the denial of recusal.

4. Sentencing Guidelines, GSR, and variances

The U.S. Sentencing Guidelines produce a Recommended Sentencing Range (GSR) based on:

• Offense level (seriousness of the offense plus adjustments like acceptance of responsibility under § 3E1.1); and
• Criminal History Category (I–VI).

But post‑Booker, the Guidelines are advisory. Courts must:

1. Correctly calculate the GSR.
2. Consider the § 3553(a) factors, including:
   • the nature and circumstances of the offense, and the history and characteristics of the defendant;
   • the need for the sentence to reflect seriousness, promote respect for law, provide just punishment, afford deterrence, and protect the public;
   • the need to avoid unwarranted disparities among similarly situated defendants.
3. Decide whether to impose a within‑range sentence, a departure, or a variance, and explain their reasoning.

A variance is a sentence outside the GSR based on § 3553(a) factors, not driven by specific guideline departure provisions. In Medoff, the upward variance from 4–10 months to 20 months was justified by aggravating, non‑Guidelines‑captured factors.

5. Waiver, forfeiture, and plain error

The opinion also illustrates the difference between:

• Forfeiture: Failure to raise an issue at the right time, potentially reviewable for “plain error” if properly framed on appeal.
• Waiver: Intentional relinquishment or abandonment—or, as in the First Circuit’s approach, failure to argue even plain error on appeal—which bars review.

By not objecting below to judge‑initiated prosecution and not arguing plain error on appeal, Medoff was deemed to have waived any claim that the structural arrangement violated separation of powers or due process.

V. Conclusion

United States v. Medoff is an important First Circuit decision that both clarifies and tightens several areas of federal practice.

On recusal, it confirms that:

• District judges may initiate and preside over criminal contempt proceedings to enforce their own civil orders (absent personal disrespect or criticism), without automatic disqualification.
• Case‑based frustration with decades of non‑compliance, skepticism about futility of civil remedies, and strong language about frivolous or tactical motions do not equate to a reasonable appearance of bias under § 455(a).
• Appellate review remains highly deferential: the objective‑observer test is applied through the lens of abuse of discretion, not as a free‑floating de novo standard.

On structural issues and preservation, the case underscores that:

• Serious constitutional objections—such as those raised by Justices in Donziger and Young—can be functionally lost to a litigant who does not timely raise them and who fails to argue plain error on appeal.

On sentencing, the decision reinforces that:

• Criminal contempt is real criminal conduct for § 3553(a) purposes.
• Guideline ranges, plea recommendations, and national averages are only starting points. Where a defendant’s conduct is unusually egregious—long‑term contempt, significant financial benefit, use of aliases, lies to the court, unscored crimes—substantial upward variances may be entirely reasonable.
• Honesty with the court and compliance with pretrial conditions are not minorities; misbehavior in those spheres can have considerable impact on sentence severity.

More broadly, Medoff sends a clear message: injunctions and court orders in securities enforcement cases are serious obligations, not symbolic gestures. Courts in the First Circuit will not hesitate to convert chronic, willful non‑compliance into significant criminal sanctions, and attempts to evade responsibility through recusal maneuvers or incomplete candor will be viewed with skepticism.

For judges, regulators, and practitioners alike, the case affirms the judiciary’s robust authority to enforce its orders through criminal contempt while simultaneously reaffirming a demanding and deferential standard for recusal under § 455(a). It also marks a notable appellate endorsement of meaningful upward variances as a tool to address persistent contempt of regulatory injunctions and to safeguard the integrity of federal court orders.