Tag Archives: plea agreement

How 2255 Motions Get Decided (And How to Write Them) – Update for August 17, 2026

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After almost two weeks off on vacation – and having enjoyed four grandkids, two leg injuries and one concussion – we’re back.

We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

4TH CIRCUIT DECISION IS THOUGHTFUL PRIMER ON 2255 LITIGATION

Curt Flood faced a life sentence when indicted in 2003. His lawyers kicked around the idea of a plea agreement with the government, but an impasse quickly became apparent: the government would come off the life sentence only if he cooperated. Curt told them that he had no interest in doing that.

Curt went to trial instead and, after he lost, he was sentenced to life. In 2011, after the Supreme Court decided Missouri v. Frye and Lafler v. Cooper – two cases that defined a prisoner’s right to effective representation where a plea offer was concerned – Curt filed a motion under 28 USC § 2255.

After 14 years of fits and starts, the 4th Circuit last week upheld the denial of his § 2255 motion. The decision is a primer on how § 2255 motions are judged at different levels of review, as well as guidance on what a prisoner must claim to succeed and should be required reading for everyone who intends to file one.

Under Rule 4 of the Rules Governing § 2255 Proceedings, a district judge must first decide whether the motion and the trial court record “conclusively foreclose[] relief” despite the 2255’s claims. For example, if a 2255 claim was that the prisoner never signed his plea agreement, the court could safely dismiss the § 2255 motion without further ado by looking at the document and the transcript of the change-of-plea hearing. If, on the other hand, the record does not contain a signed plea agreement and the prisoner was not asked whether he had seen and agreed to its terms, Rule 8 would require the court to order additional briefing and the collection of evidence. Based on that additional record, the court may find that an evidentiary hearing is needed.

The standards by which the 2255 claims are reviewed at each stage have always seemed squishy. What is “conclusively?” And what standard applies to a court’s decision to hold an evidentiary hearing after Rule 8 briefing? Last week’s 4th Circuit decision addressed those questions, comparing Rules 4 and 8 to civil litigation and providing structure to 2255 proceedings that should benefit serious movants.

“When we review a district court’s denial of a § 2255 motion at the Rule 4 stage,” the Circuit ruled, “we are guided by the principles governing review of a [Fed.R.Civ.P.] 12(b)(6) dismissal. So we ‘accept a petitioner’s well-pleaded allegations as true,’ and ask whether the record conclusively forecloses relief notwithstanding those allegations. And when a district court denies a § 2255 motion at the Rule 8 stage—after receiving additional briefing and evidence, but without holding an evidentiary hearing—’we treat the district court’s decision like a grant of summary judgment.’ So we will affirm a district court’s denial of relief without a hearing when the record leaves ‘no genuine dispute as to any material fact.’ Fed.R.Civ.P. 56(a). In so doing, we do not weigh evidence or make credibility determinations. And at both the Rule 4 and Rule 8 stages, we draw all reasonable inferences in the movant’s favor.”

The 4th’s opinion illustrates why a 2255 movant has to ensure that his or her argument is consistent. Curt claimed in his § 2255 motion that his attorneys were ineffective because “they failed to seek a plea agreement… [and] “never even engaged in plea discussions.” But in the same filing, he acknowledged that when the government approached his lawyers about a plea, they met with the prosecutors to discuss it. “In those discussions, the government made clear ‘that in order to receive an offer, Mr. Flood would have to proffer’,” and Curt had already told his attorneys that he would never do so.

However Flood frames counsel’s alleged deficiency, the claim fails. Read as a charge that counsel ‘never even engaged in plea discussions,’ it founders on the record: By Flood’s own admission, his counsel met with the prosecutors and learned that the government’s terms required cooperation. Read instead as a charge that counsel, having met with prosecutors to discuss a plea, should have done something more or pressed harder, it identifies no act or omission that fell outside the wide range of reasonable professional assistance. ‘Try harder’ or ‘do more’ is not a Strickland theory… Absent some specification of counsel’s deficient acts or omissions, the record and filings conclusively show that Flood is not entitled to relief.

Oliver Wendell Holmes, Jr., once said, “The language of judicial decision is mainly the language of logic.” A 2255 movant should spend extra time ensuring that his or her evidence and arguments tell a coherent and substantial story.

United States v. Flood, Case No. 23-7032, 2026 U.S. App. LEXIS 24462 (4th Cir. Aug. 13, 2026)

~ Thomas L. Root

5th Circuit Emasculates SCOTUS Hunter Decision – Update for August 4, 2026

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We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

WE’RE OUTTA HERE

One week a year, we take a break from the newsletter. That will be next week, while we are abused by our grandkids on vacation.  THERE WILL BE NO NEWSLETTER ON AUGUST 10, 2026. We will be back on August 17th.

THE ORANGUTANS SPEAK?

A little more than a month ago, the Supreme Court ruled that appeal and collateral attack waivers contained in plea agreements were not rigid but instead should be found to be “unenforceable when it would result in a miscarriage of justice — meaning, when it would leave in place the kind of egregious sentencing error that would bring the judicial system into disrepute.”

The decision, Hunter v. United States, reversed a 5th Circuit policy that refused to set aside waivers for any error whatsoever. SCOTUS held that the error in the sentencing must be obvious, not one that a judge could reasonably make.” The high court ruled that “[t]he point of the miscarriage-of-justice limit… is to offer a safety valve for extreme cases—a way out of waiver when the system’s integrity is at stake.”

The Court further explained the types of situations that would qualify for the miscarriage-of-justice exception:

A defendant may appeal a sentence exceeding what the relevant statute allows—most commonly, a term of years above the maximum prescribed. Second, a defendant may appeal a sentence infected with a blatant constitutional error, such as when a judge takes account of a constitutionally impermissible factor (like race) or imposes a constitutionally infirm condition of supervised release (like barring a defendant from becoming pregnant). And third, a defendant may appeal if his sentence was imposed without some minimum of civilized procedure, as in, yes, the [trial by] twelve orangutans case—or less extravagantly, one in which the judge refused to hold a hearing consonant with basic principles of law.

SCOTUS said other more “uncertain or ordinary” errors would not override an appeal waiver. It observed that “mistakes” in “the detailed calculation of a Sentencing Guidelines range and the mandatory consideration of multiple sentencing factors” are “unfortunate but inevitable… and  cannot cancel an appeal waiver.”

In the Hunter case, defendant Munson – convicted of a white-collar offense – was ordered to get mental health therapy while on supervised release and to take whatever medication his mental health provider told him to take. Munson was uninterested in downing the drugs some psychiatric doc ordered. He did not appeal his sentence but rather the mental health condition in his supervised release, making a 5th Amendment argument that he couldn’t be told to dope himself up by the court.

The Supreme Court did not settle the matter for Munson. It just told the 5th Circuit that it couldn’t automatically reject the appeal without testing the waiver provision against a miscarriage of justice standard.

Last week, the 5th Circuit applied the new standard but unsurprisingly found against Munson once again. The Circuit held that a court order that a defendant be doped up against his will is normal and acceptable, because “there is a nexus between the Medication Condition and the government’s interests in promoting Hunter’s health and reducing his likelihood of re-offending.” Plus, he could always appeal to the District Court if a “dispute” arose about Hunter’s taking particular medication, and “the probation officer can’t resolve the dispute,” and, anyway, the meds will be prescribed by a physician who, the Court assumes, will not “prescribe mental health medication against Hunter’s medical interest.”

Additionally, the Medication Condition “does not rise to the level of ‘egregious” constitutional error that would ‘bring the judicial system into disrepute’ because the same condition has been “broadly imposed” by federal district courts “as a ‘stock’ special condition” of supervised release.” Finally, the condition is nothing like the Hunter opinion’s examples of race-based or gender-based terms that would be “blatantly unconstitutional.” Such errors would “stem from extreme animus or prejudice,” the Circuit said, “which are never appropriate considerations in sentencing. In contrast, there is no suggestion here that the district court imposed the Medication Condition for such invidious purposes.”

No one expected the 5th to roll over after the SCOTUS Hunter opinion slapped down its “waivers-are-bulletproof” policy. However, its quick and dubious defense of a district court’s decision to practice psychiatric medicine on a white-collar defendant – complete with anodyne justifications that could fit any case – suggests that SCOTUS has a lot more oversight to apply to appeals waiver enforcement.

United States v. Hunter, Case No 24-20211, 2026 U.S. App. LEXIS 22637 (5th Cir. July 29, 2026)

~ Thomas L. Root

Hunting for ‘Miscarriages of Justice’ in Hunter – Update for July 14, 2026

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We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

SCOTUS WAIVER CASE IGNITES ARGUMENT OVER WHAT CONSTITUTES A ‘MISCARRIAGE OF JUSTICE’

A Supreme Court decision from last term, Hunter v United States, may seem to be a yawner to many federal prisoners. But some legal commentators are suggesting that the decision, while “murky,” may be “the most important criminal case of the term.”

The importance of Hunter, which held that appellate and collateral attack waivers in plea agreements may not be enforced by the government where to do so would lead to a miscarriage of justice, has already led to a number of Supreme Court GVRs. (A ‘GVR’ is a single SCOTUS order that grants certiorari (the ‘G’), vacates the lower court decision (the ‘V’) and remands the case (the ‘R’) for consideration in light of a new Supreme Court decision that addresses the same issue that the GVR case raises).

An appellate waiver, in which a defendant waives his or her rights to appeal or file a collateral attack except in very limited cases, is a feature of virtually all of the 94% or so of federal criminal cases resolved each year by plea bargain. Some are bare bones. Others are breathtakingly expansive, waiving rights to direct appeal, habeas corpus under 28 USC 2241 and 2255, compassionate release motions, and even retroactive Guidelines changes.

Last month’s GVR list of 17 cases – an unusually large number – suggests that a lot of appellate cases will be exploring the limits of what constitutes a “miscarriage of justice” sufficient to set aside a plea agreement appellate waiver.

Last week, Ohio State University law professor Doug Berman listed “a notable group of early test cases for the ‘miscarriage of justice’ limit on the enforceability of sentencing appeal waivers” provided to him by a law professor reader of his blog:

    • A claim that the sentencing judge imposed sex offender registration for a non-registrable offense;
    • A claim that a restitution order was not supported by sufficient evidence;
    • A claim that the sentencing judge failed to give the defendant much less credit for substantial assistance to law enforcement than the government recommended;
    • A claim that defense counsel was ineffective in stipulating that a prior state conviction was a serious violent felony (increasing the federal sentence exposure), even though the ineffectiveness did not affect plea negotiations;
    • A claim that the defendant’s guilty plea to an offense (such as possessing a firearm as a drug user) after SCOTUS decisions (such as Hemani) undercut the constitutionality of the crime;
    • A claim that the sentencing judge erred in applying a Guidelines career offender enhancement to the defendant, which increased his guideline range by 60% or more; and
    • A claim that the sentencing judge imposed a substance abuse testing special condition on a defendant’s supervised release which delegated the frequency of testing to the Probation Office.

The Supreme Court did little more than say that a “miscarriage of justice” was something so outside the bounds of conscience as to call the entire “judicial system into disrepute.” William Otis, a former Assistant U.S. Attorney (and ex officio member of the Sentencing Commission) – a serial antagonist of Prof. Berman on the Sentencing Law and Policy blog site – complained, “I was an appellate lawyer in a big USAO for about 20 years, and I can tell you how many sentences fit that description — pretty darn close to zero.”

Being familiar with Mr. Otis’s positions over the years, I am hardly surprised that he never saw a draconian sentencing issue that shocked his conscience.

Another commentator observed that Hunter seemed to confirm validity of appeal waivers while noting problems with the “contract analogy” – the judicial fiction developed over years of plea agreement jurisprudence that such deals – including the defendant’s waiver of appellate and collateral rights – are just contracts between parties to be judged by the well-developed common law of contracts (leavened by some nod to the fact that the defendant is surrendering constitutional rights while the government is merely forgoing the chance to heap more punishment on its target).

Whether the Hunter “miscarriage of justice” is just a restatement of an existing standard or the dawn of an era where the fundamental balance between a defendant on the one hand and the might of the government on the other is, for now, as “murky” as Prof. Berman and Jonathan Wroblewski suggest it is in their excellent analysis of Hunter.

No doubt, we will see a lot of case-specific litigation in the coming years over when Hunter will let a defendant walk away from an appellate waiver.

Hunter v. United States, 608 U.S. —, 146 S. Ct. 1702, 2026 U.S. LEXIS 2558, 2026 LX 319193, 31 Fla. L. Weekly Fed. S 811 (June 18, 2026)

Sentencing Law and Policy, Early efforts in the hunt to understand Hunter’s new limits on the enforceability of sentencing appeal waivers (July 8, 2026)

Supreme Court, Order List (June 29, 2026)

Berman and Wroblewski, The Supreme Court Draws a Murky Line; The Sentencing Commission Should Help Clarify It  (June 22, 2026)

 ~ Thomas L. Root

Defendants Waiving The Waiver – Update for June 23, 2026

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SCOTUS HOLDS APPELLATE WAIVERS AREN’T ALWAYS IRONCLAD

Just about the last thing any defendant is concerned with when signing a plea agreement with the federal government is the fine print in which she waives the right to appeal or file a post-conviction 28 USC § 2255 petition or a related motion. The agreed-upon sentence, Guideline factors, dismissed counts, and the US Attorney’s promise not to prosecute for anything else are the important questions. Technicalities like waiving appeal and collateral rights, restitution, supervised release… those provisions are usually just so much noise to a defendant who is negotiating away freedom while trying to minimize the pain.

The appellate and collateral attack waiver is not important.

Until it is.

That is, until the parties’ agreement that the Guideline sentence should be between 33-41 months runs into a judge who thinks the statutory maximum sentence of 20 years is more appropriate. The right to appeal such craziness then becomes vitally important. And that’s when the government waves the waiver at the court of appeals, demanding that your appeal be tossed because, after all, you agreed not to appeal.

In 2024, Munson Hunter III signed a plea deal to plead guilty to aiding and abetting wire fraud. The agreement included the standard appeal waiver. The government dismissed nine other counts as part of the package in exchange for Munson’s agreement to a 51-month sentence.

At sentencing, the court accepted the deal, imposing a 51-month sentence. However, concerned that Munson exhibited conduct that suggested some mental issues, the court added a condition that Munson get mental health treatment while on supervised release and take whatever meds the mental health provider prescribed.

Munson was uninterested in spending his supervised release in a drug-induced stupor and tried to appeal, claiming a 5thAmendment right not to be forced to take pills. The 5th Circuit ruled that his appeal waiver barred him from doing so.

Last week, the Supreme Court reversed the Circuit.  Writing for the majority, Justice Elena Kagan explained that “an agreement not to appeal a sentence is unenforceable when it would result in a miscarriage of justice—meaning, when it would leave in place the kind of egregious error that would bring the judicial system into disrepute.”

The result was not a watershed moment.  After all, eight Circuits already recognize the “miscarriage of justice” exception. But the opinion is notable for the explanation of what constitutes a “miscarriage of justice,” which up to now has been largely an “I can’t define it, but I know it when I see it” standard.

The 8-1 opinion described “miscarriage of justice” as being where

the sentence is marred by the kind of egregious error that would bring the judicial system into disrepute. The error must be obvious—not one a judge could reasonably make. And it must be of the type that would undermine public confidence in the judiciary. Sentencing is a complex affair in our criminal justice system, involving for example the detailed calculation of a Sentencing Guidelines range and the mandatory consideration of multiple sentencing factors. In that endeavor, it is unfortunate but inevitable that mistakes will occur. Such standard-fare errors in misapplying sentencing law cannot cancel an appeal waiver. Were they to do so, the utility of waivers in plea negotiations could plummet: such a provision would have less value to the Government, and so might induce fewer concessions to a defendant. And still more to our point, that kind of standard error is not likely to discredit the judiciary’s commitment to law. But some faults in sentencing can…The point of the miscarriage-of-justice limit, as many appellate courts have properly applied it, is to offer a safety valve for extreme cases—a way out of a waiver when the justice system’s basic integrity is at stake.

Armed with this definition, a well-prepared defendant in many cases may be able to make a compelling showing to get around an appeal waiver. Expect that many cases will follow that include detailed arguments to set aside appeal and post-conviction waivers.

Hunter v. United States, Case No. 24-1063, 2026 US LEXIS 2558 (June 18, 2026)

~ Thomas L. Root

Guilty Pleas Are Solid and Eternal – Update for February 10, 2026

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DIAMONDS AREN’T FOREVER – BUT PLEA AGREEMENTS ARE

When I was a kid, I learned in grade school that diamonds are formed by immense pressure over immense time, and that humanity would never be able to make diamonds because we couldn’t begin to duplicate nature’s processes.

It turns out that Mrs. McGinnis – my 6th grade teacher – was wrong. The diamond business is being upended because factories can now crank out the glistening lab-grown stones, making diamonds’ rarity commonplace and prices plummet.

So James Bond was wrong, too.  Diamonds are not forever.

Last week, however, two Circuits reminded us that plea deals and guilty pleas last longer and are more solid than any chunk of compressed carbon shining on your beloved’s finger.

Waivers Are Forever – Brandi Appleton pled guilty to drug distribution and a felon-in-possession charge. Her plea agreement included the usual waiver of her right to appeal the sentence. Although the Guidelines recommended 41 to 51 months given Brandi’s offense level and criminal history, the district court sentenced her to five years of probation due to her difficult childhood, drug addiction, and the fact that she would probably lose her parental rights if she was locked up. The court was impressed by Brandi having completed a residential drug treatment program and her employment history while on pretrial release.

But Brandi’s good fortune didn’t last. Six weeks into the probation, she was arrested for possession of personal use drugs. The court revoked her probation and gave her 44 months.

Brandi appealed the sentence, but last week, the 6th Circuit threw out the appeal because of her plea agreement waiver.

Brandi argued that the waiver no longer counted because the imprisonment was imposed only after a probation-revocation hearing. The 6th, however, ruled that “revocation sentences are part and parcel of the sentence underlying the original conviction, not a freestanding, unrelated sentence.” Brandi’s initial probation depended on compliance with the terms of supervision, so that her “subsequent term of imprisonment following the revocation of probation was a sentence for the same underlying offense addressed in [the] initial sentence. It follows that Appleton’s appeal waiver applies to the sentence imposed at her probation revocation hearing.”

Unlike diamonds, plea waivers are forever.

Answers Are Forever – Steve Boria took medications for sleeping problems and bipolar disorder the night before he pled guilty to a drug conspiracy and gun charge. During the plea hearing, the district court learned that Steve had taken these medications and asked several follow-up questions to confirm that he understood the proceedings and felt “clearheaded.” Steve decided to challenge his conviction and sentence on appeal despite an appeal waiver in his plea agreement, arguing that the district court violated F.R.Crim.P. 11 and his constitutional rights because it did not ask enough about the impact of his medications.

Last week, the 2nd Circuit disagreed. The judge asked what he had taken, when he had taken it, and whether he understood what was going on in court. Steve said he did. The Court said Steve’s “conduct during the plea hearing raised no red flags,” so the district court fulfilled its Rule 11 obligation to “explore on the record defendant’s ability to understand the nature and consequences of his decision to plead guilty” by confirming that Steve understood the proceedings and felt clearheaded.

Steve’s clear answers to the Judge’s clear questions were binding.

Steve’s additional problem was that his lawyer did not object at the time that the Court had not asked enough, so Steve had to show “plain error,” that is, an obvious mistake that raised a reasonable probability that Steve would not have pled guilty but for the alleged error. This is a great example of the reason for F.R.Crim.P. 52(b) “plain error.” If Steve’s lawyer had objected at the time, the judge probably would have postponed the plea hearing, thus solving the medication problem.

United States v. Appleton, Case No. 25-5051, 2026 U.S.App. LEXIS 3687 (6th Cir., February 5, 2026)

United States v. Boria, Case No. 24-1871, 2026 U.S.App. LEXIS 3472 (2d Cir. February 4, 2026)

~ Thomas L. Root

SCOTUS Will Decide When a Waiver Has Been Waived  – Update for October 14, 2025

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WAVING GOODBYE TO WAIVER CONFUSION?

The Supreme Court last Friday granted review to a federal criminal case asking whether a plea agreement appeal waiver binds a defendant where the judge advised him that he had the right to appeal.

Munson Hunter pled guilty to aiding and abetting wire fraud. He signed a plea agreement that, among other things, provided that he was giving up his right to appeal.

At sentencing, a the judge imposed a mental health condition over the defendant’s objection and then told the defendant, “You have a right to appeal.”

Munson appealed the mental health condition to the 5th Circuit, which – pointing to his appeal waiver – dismissed the appeal.

SCOTUS will address two issues:

Whether the only permissible exceptions to a general appeal waiver are for claims of ineffective assistance of counsel or that the sentence exceeds the statutory maximum.

Whether an appeal waiver applies when the sentencing judge advises the defendant that he has a right to appeal, and the government does not object.

A Circuit split exists on the issue. In the 9th Circuit, if a sentencing judge advises a defendant of a right to appeal and the government fails to object, the appeal waiver in the plea agreement has no effect.

The Supreme Court will now settle the issue.

Hunter v. Texas, Case No 24-1063 (certiorari granted October 10, 2025)

SCOTUSBlog, Court grants criminal case on right to appeal (October 10, 2025)

~ Thomas L. Root

An Offer You Can’t Refuse – Update for May 21, 2025

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We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

LET’S MAKE A DEAL

letsmakeadeal250522Bad, bad Leo Brown… Well, maybe not so bad, but in bad trouble. In October 2016, Edwin Leo Brown was indicted on four counts of possession with the intent to distribute crack cocaine and a fifth count for being an 18 USC § 922(g)(1) felon in possession (F-I-P) of a gun. Leo was looking at a maximum sentence of 20 years’ imprisonment on each of the four drug charges, and up to 10 more on the F-I-P count.

Leo’s lawyer, Frank Harper, negotiated with the government, ultimately getting two plea agreements—one of which called for Leo to cooperate with the Feds and one of which did not—that both called for Leo to plead guilty only to the F-I-P count. That meant that taking either deal would limit Leo’s sentence to ten years. Harper advised Leo that he should take one of the plea agreements or the other, but Leo was skeptical. When Leo told Harper that he felt like the lawyer could have gotten him a better deal than 10 years, Harper apparently responded in exasperation, “It’s not my fault why you’re facing ten years.”

That offended Leo, who “from that moment” did not “trust [Harper’s] judgment” and told him so. The relationship deteriorated, and Harper subsequently withdrew as counsel.

Enter affable lawyer Brett Wentz. Leo liked Wentz, who agreed that Leo would face a firm sentence of 10 years if he took either plea deal, but told him that even if he did not–instead just entering an “open plea” to all counts without any–Leo’s sentencing guideline range would be the same. “In other words,” as the 4th Circuit described it, “Wentz advised Brown that he would be facing a statutory maximum of ten years’ imprisonment regardless of whether he accepted a plea offer or not.”

Leo really wanted to preserve his right to appeal, which he would have to waive under either version of the plea agreement. So after Wentz told him he’d get no more than 10 years with or without a plea deal, Leo thought it was a no-brainer. He rejected the plea offers and entered a guilty plea to all counts without benefit of a plea agreement.

harper250522At his change-of-plea hearing, the judge told Leo that he faced up to 20 years’ imprisonment on each of the four drug charges. At that point, Leo and lawyer Wentz conferred off the record. Leo then told the court he understood the penalties. The judge proceeded to tell Leo that he faced 10 years on the F-I-P. Leo again talked to Wentz off the record before telling the court he understood that potential penalty, too.

Unless there’s a plea deal that requires a particular sentence, the judge always tells a defendant during a change-of-plea hearing that even if defense counsel had given him an estimate of what the sentence might end up being, that estimate is not binding on the court. Leo’s judge told him this, but Leo “affirmed that he understood and subsequently entered an open guilty plea as to all five counts.”

You can see where this is headed, but Leo couldn’t. At sentencing a few months later, the court hammered Leo with 210 months’ imprisonment—17½ years—on all counts, an upward departure from the advisory guideline sentencing range of 87 to 108 months. Leo was not pleased.

After his sentence was affirmed on appeal, Leo filed a 28 USC § 2255 post-conviction motion arguing that Wentz provided ineffective assistance in giving Leo wrong advice on taking the plea deal.

Relying on the Supreme Court decision in Lee v. United States, the district court ruled that it would “not upset a plea solely because of post hoc assertions from a defendant about how he would have pleaded but for his [counsel’s] deficiencies.” Instead, it would look to “contemporaneous evidence to substantiate a defendant’s expressed preferences.” Based on the record, the district judge found, “even if Wentz had properly advised Brown about his sentencing exposure… Brown would not have signed the non-cooperation plea agreement with an appellate waiver and pleaded guilty to count five pursuant to the plea agreement” because avoiding having to “waivi[e] his right to appeal was more important to Brown than his sentencing exposure.”

On Tuesday, the 4th Circuit reversed the judgment, holding that Lee was the wrong standard to apply and that Leo had “demonstrated a reasonable probability that, but for Wentz’s erroneous advice regarding sentence exposure, he would have accepted the government’s offer.”

The 4th held that “the biggest distinction” between Lee and Leo’s case “is that Lee concerned an individual who accepted a guilty plea offer, while the instant appeal concerns an individual who rejected a guilty plea offer.” The Circuit said that the proper standard where a plea deal is rejected is set out in Missouri v. Frye and Lafler v. Cooper, a pair of Supreme Court decisions from 2012 that “articulated a different way to show prejudice” where a plea deal is not accepted, which is the issue in Leo’s case.

coulda250522A defendant who argues he rejected a plea offer because of ineffective assistance of counsel “need not present contemporaneous evidence to support his ineffective assistance claims,” the 4th Circuit said. Instead, a reasonable probability that a defendant would have accepted the plea offer but for counsel’s bad advice was met here by Leo’s testimony that he “would have taken the plea that the Government offered [him]” had he known he was facing a theoretical maximum of 90 years’ imprisonment, and that he believed, based on Wentz’s advice, that his “maximum exposure” when he pleaded to all five counts was “[n]o more than ten years.” The very fact that Leo pled guilty to more serious charges—namely, receiving 17.5 years’ imprisonment when the government’s plea offer offered a max of 10 years—was alone enough to show a “reasonable probability” Leo would have taken the deal, the Circuit said.

The Circuit ordered the case remanded and that Leo be offered the original 10-year deal.

United States v. Brown, Case No. 22-7105, 2025 U.S. App. LEXIS 12211 (4th Cir. May 20, 2025)

Lee v. United States, 582 U.S. 357 (2017)

Missouri v. Frye, 566 U.S. 134 (2012)

Lafler v. Cooper, 566 U.S. 156 (2012)

– Thomas L. Root

Government ‘Dog Whistle’ Called Out by 1st Circuit – Update for January 31, 2025

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UNFORCED ERROR

unforcederror250131Mario Castillo, a 72-year-old grandfather, was convicted of sexually abusing his granddaughter, a federal crime because it happened in post housing at a military installation. His plea agreement with the government let the parties argue for widely divergent sentences: Mario argued that the Guidelines should result in a 78-month sentence. The government said the range was 235-293 months but agreed to ask for a sentence of 180 months.

At his first sentencing, the district court – which itself was not bound by the plea agreement to any limits – imposed a 235-month term. The 1st Circuit then vacated the sentence because of a procedural error in calculating the Guideline range.

At his resentencing, Mario began by acknowledging that the court had the authority to impose a sentence without regard for his 78-month proposal or the Government’s 180-month proposal. He argued, however, that his age, minimal risk of re-offending, and prior difficulties in prison should convince the district court to sentence him leniently.

hammer160509The government was not so constrained. Without any prompting by Mario’s anodyne sentencing arguments or questions from the district judge, repeatedly emphasized that the court had the authority to impose a harsher sentence than the 180-month recommendation that it was bound by the plea agreement to request. The government told the court, for example, that

● “We were bound by [the plea agreement], but we did not bind the court in any kind of agreement, and the court is free to sentence anywhere it wants, and the victims are free to argue for anything that they want as well.”

● “Your Honor stated [at the first sentencing] that the court had considered all of the other sentencing factors… and that neither sentence recommendation… was just… which resulted in… the sentence that you imposed at that time.”

● “This court’s sentence, whatever it is, can aptly be supported by the facts and arguments that the United States made in its sentencing memorandum filed in 2018.”

● “Your Honor is still free and legally unimpeded to sentence to whatever he wants between probation and life. That was true [at the first sentencing], it is true today.”

● “The… Court of Appeals did not… say the original 235-month sentence was an unreasonable sentence… or that it was too harsh a sentence….”

● “We are here on a procedural error that has nothing to do with the running room that Your Honor has to sentence.”

The government also repeatedly suggested that public safety required that Mario never leave prison, even though he would be deported right away to the Dominican Republic. The prosecutor said he was “very fearful for the children” in the Dominican Republic” because – regardless of his age – Mario “will sexually offend against children [because] [h]e is attracted to them, and he is going to act on his attraction whenever the opportunities appear.”

The district court heard the prosecutor’s dog whistle loud and clear, and reimposed the 235-month sentence.

dogwhistle240610Last Tuesday, the 1st Circuit vacated the sentence again, holding that the government breached its plea agreement obligations and violated Mario’s due process rights.

“In our view,” the Circuit said, “the prosecutor’s sentencing presentation constitutes a clear example of paying lip service to the plea agreement while giving a wink and nod to the imposition of a harsher sentence…” The government’s arguments, unprompted by Mario’s sentencing presentation, were an unforced error, “leav[ing] the unmistakable impression that the prosecutor wanted the district court to impose a sentence longer than 180 months…. That was not the government’s promise. This case thus presents an instance of a prosecutor reaffirming a promise to the defendant out of one side of his mouth while simultaneously trying to subvert it out of the other side.”

The government contended that it never actually endorsed a 235-month sentence. “That is true,” the 1st Circuit conceded, “but our caselaw permits a successful breach claim where a prosecutor pays mere ‘lip service’ to a plea-agreement promise… [T]he prosecutor suggested that the district court reimpose the same 235-month sentence without explicitly saying so. Thus, this is a circumstance where the prosecutor… undercut a plea agreement while paying lip service to its covenants.”

The Circuit ordered that Mario get resentenced before a different judge.

United States v. Castillo, Case No. 21-1599, 2025 U.S. App. LEXIS 1887 (1st Cir. Jan. 28, 2025)

– Thomas L. Root

Local Lawyer Makes Bad – Update for December 10, 2024

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We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

PLEA AGREEMENT BY COMMITTEE

pleadeal161116Elvin Torres-Estrada hired a pair of New York City lawyers to represent him in a Puerto Rican drug conspiracy case. When out-of-district laws come to town in a case like this, they have a local lawyer sponsor them to appear pro haec vice, literally “for this event,” without having to get admitted to practice before the district court. Elvin hired a local lawyer, Garcia, to do so and to act as local counsel to his out-of-town hired guns.

Early on, Elvin’s lawyers concluded that he might benefit from a joint plea deal with one of his co-defendants. With Elvin’s OK, the two attorneys began coordinating with the co-D’s attorneys and learned the government had refused a proposed 11-year term of imprisonment for the co-defendant and would be seeking a sentencing recommendation for Elvin roughly two years longer than whatever the co-D ultimately got. Local lawyer Garcia did not attend most of their meetings with the co-D’s people, consistent with his limited role as local counsel.

The government offered Elvin 188 months. Elvin’s NYC lawyers got the co-D’s lawyers to agree that the defendants would jointly counteroffer with 144 for the co-D and 168 for Elvin. Elvin reluctantly OK’d the deal. But before the scheduled meeting with the government, Garcia met with his client and talked him into authorizing a 156-month counter instead of the previously agreed-to 168. When the New York lawyers found out, they convinced Elvin to raise it to 164.

Garcia then blindsided the NYC lawyers by throwing the 156-month counteroffer out in the middle of the meeting anyway, and then upping it to 162 when the government rejected the 156 months out of hand. The government said it would “think about” it.

Plea negotiations broke down, the government obtained a second indictment against Elvin for a separate conspiracy, and he ended up with a 288-month sentence. Elvin filed a 28 USC § 2255 petition arguing that Garcia rendered ineffective assistance by undercutting the New York lawyers’ careful plea negotiations.

Last week, the 1st Circuit upheld the denial of Elvin’s 2255.

chinashop241210The Circuit seemed to acknowledge that Garcia was a bull in a china shop but said that he had compromised with a counteroffer that was only two months lower than what Elvin had authorized and that the government “still responded by saying he would think about it.” The 1st said, “The circumstances surrounding the meeting thus diminish the force of Elvin’s claim that Garcia’s disruptive actions were incompatible with an attempt by competent counsel to secure the best possible deal for his client. Given the government’s stated willingness at the meeting to consider the rogue 162-month proposal, one could reasonably say that Garcia’s aggressive (though discourteous) tactics had advanced the plea negotiations and, accordingly, were within the range of competence demanded of attorneys in criminal cases.”

reallawyer170216Even if Garcia’s performance had been deficient, the Circuit said, Elvin had not been prejudiced. The record “makes plain that Garcia’s conduct did not result in termination of the plea-bargaining process. Rather… after [the government] was told that Garcia “spoke out of turn and inconsistent with Elvin’s instructions,” it “agreed to revisit” the possibility of lowering the offers to both defendants. And more than two weeks after Garcia’s hijacking of the negotiation session, the original offer of fifteen years/eight months (188 months) remained on the table.”

“In sum,” the Circuit held, “we need not view Garcia’s disruptive performance in advance of, and during, the meeting as entirely defensible to conclude that Elvin has failed to establish a violation of his 6th Amendment right to the effective assistance of counsel…

Torres-Estrada v. United States, Case No. 19-1485, 2024 U.S. App.  LEXIS 30919 (1st Cir., December 6, 2024)

– Thomas L. Root

3rd Circuit Holds Lawyer’s Sentence Misadvice is Ineffective Assistance – Update for July 29, 2024

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We post news and comment on federal criminal justice issues, focused primarily on trial and post-conviction matters, legislative initiatives, and sentencing issues.

WHEN LAWYERS AREN’T JUST WRONG, BUT VERY, VERY WRONG

It’s long been held that a lawyer’s duty during plea negotiations is to advise a defendant on the strength of the government’s case and the difference between the sentence you’d get at trial and the one you’ll get taking the plea. But what if your lawyer blows it?

wrong160620Many a prisoner has complained in a § 2255 motion that his or her lawyer badly misestimated the sentence, and if counsel had gotten it right (or close to right), the defendant would have accepted the deal. And many of those prisoners have lost their 2255s because the court holds that their lawyers’ bad guesses are not the same as ineffective assistance.

But sometimes, the miss is just too wide.

Steven Baker had committed a series of armed bank robberies. When he faced trial in 2010, Steve’s attorney advised him that he faced a total of 15-17 years’ imprisonment if he accepted a government offer to plead to one robbery and one 18 USC § 924(c) gun charge, but if he didn’t take the deal, the government would charge him with two other armed robberies. Counsel said the three potential § 924(c) counts would give him 21 years consecutive to his bank robbery Guidelines.

Wrong, wrong, wrong. This was all before the First Step Act passed in 2018, so Steve faced a consecutive 57-year mandatory minimum sentence under the § 924(c) “stacking” provision then in effect. Based on the difference between 17 years with a plea and 21 years rolling the dice at trial, Steve turned down the plea. He was charged with the other robberies and went to trial, where he, of course, was convicted on all counts. He got 57 years on the § 924(c) counts plus 87 months more on the bank robbery charges.

Steve filed a § 2255 motion claiming his lawyer was ineffective in advising him so badly about 21 years versus 57 years. The district court turned him down, but last week, the 3rd Circuit vacated his conviction.

pleading170502“When addressing a guilty plea, counsel is required to give a defendant enough information to make a reasonably informed decision whether to accept a plea offer,” the Circuit held. “We have little difficulty concluding that this more than three-decade miscalculation of Baker’s sentence exposure on the three potential § 924(c) counts is objectively unreasonable.”

The bigger issue was whether Steve had proven he was prejudiced, that is, that he would have taken the 17-year plea deal if his lawyer had accurately explained the likely 57-year stacked sentence if he went to trial. The trial court found Steve’s testimony that he would have taken the deal to lack credibility, but the 3rd Circuit said the very fact that the difference between the 21 years estimated by counsel and the 57 years plus he got was all the evidence it needed.

Considering the sentence-exposure disparities as evidence of prejudice “makes good sense,” the 3rd ruled.

A great disparity provides sufficient objective evidence—when combined with a defendant’s statement concerning his intentions—to support a finding of prejudice… Moreover, while a defendant’s calculus in accepting or rejecting a plea offer may involve many variables, knowledge of the comparative sentence exposure between standing trial and accepting a plea offer will often be crucial. Large sentence-exposure disparities weigh directly on this “crucial” decision.

hammer160509Steve’s actual sentencing range was “extraordinarily greater than the 15-17 years he would have received had he accepted the plea offer,” the Circuit said. “As Baker states, the 57-year mandatory minimum alone would almost certainly mean that he would ‘die in prison.’ This great sentence-exposure disparity, the true scope of which Baker did not know due to his counsel’s underestimate of the sentence for the potential firearm charges, weighs heavily in favor of prejudice.”

Baker v. United States, Case No. 23-2059, 2024 U.S. App. LEXIS 18333 (3d Cir., July 25, 2024)

– Thomas L. Root