Tag Archives: ineffective assistance

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

Santa Courts Deliver Post-Conviction Coal – Update for December 18, 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.

A CHRISTMAS LIST

A few appellate court holdings for your stocking (even if they seem to be lumps of coal):

Incompetence Here and There: Airrion Blake was convicted of tax fraud. Two months after his conviction, his attorney was thrown off the roster of attorneys allowed to practice in the 7th Circuit after “flagrantly disregard[ing]” the district court’s instructions in a civil case that “raise[d] serious concerns about his professional competence.”

Airrion filed a 28 USC § 2255 petition claiming that his lawyer’s disciplinary proceedings should negate any presumption that he was professionally competent in Airrion’s case. Last week, the 7th Circuit disagreed, reaffirming that ineffective assistance claims require case-specific analysis.

The court found that while Airrion’s lawyer misunderstood Brady obligations, Airrion failed to show how that prejudiced his case. Airrion admitted on the stand that his tax return was false, and ample evidence supported his conviction. Thus, there was no reasonable probability that correcting counsel’s errors would have changed the outcome.

Blake v. United States, Case No. 23-2399, 2025 U.S.App. LEXIS 32146 (7th Cir. Dec. 9, 2025)

No Need To Double Count: Jefferson Washington was convicted of a drug offense in 2020. His sentencing range would have been 24-30 months, but he was held to be a Guidelines career offender, making his sentencing range 151-188 months.

A few years later, the 4th Circuit held that Jeff’s predicate offenses did not qualify for career offender status. Jeff filed for compassionate release under 18 USC § 3582(c)(1)(A), arguing that the gross sentence disparity between what he got in 2020 and what he would get today was an extraordinary and compelling reason for a reduction, and that the same disparity should be considered when the court weighed the 18 USC § 3553(a) sentencing factors.

The district court denied relief.

It agreed that Jeff had demonstrated that he had an extraordinary and compelling reason for a sentence reduction based on the “enormous disparity” between the career offender Guidelines range at sentencing and what it would be if his career offender status were eliminated. Despite that determination, the court ruled that compassionate release was not justified under the § 3553(a) sentencing factors because of Jeff’s “significant criminal history” – dating back some thirty years and including a collection of non-violent and violent offenses showed “disrespect for the law.” The court held that Jeff’s commendable rehabilitative efforts weren’t enough to convince it that he posed ‘a reduced danger to himself or his community.” Jeff argued that his time served was more than the top end of his guidelines if he had been sentenced today, but the court didn’t discuss that argument in its decision denying Jeff’s compassionate release motion.

“We… reject Washington’s argument that the court abused its discretion by failing to explicitly address the sentencing Guidelines range disparity… as part of its § 3553(a) discussion,” the 4th Circuit held. “[D]istrict courts are not required to restate views expressed in its “extraordinary and compelling” analysis in its § 3553(a) analysis. And… on appellate review… we consider the totality of [the court’s] statements rather than view them in isolation.”

The 4th ruled that the “district court’s reasoning demonstrates that it was fully aware of the extent of the sentencing disparity at issue here and that it factored in Washington’s favor… [N]othing required the district court to… readdress this same point when considering the other statutory factors relevant to its decision whether to grant relief… [B]ecause the record demonstrates that the district court understood and explicitly engaged with Washington’s Guidelines range disparity as part of its decision to deny relief, it was not required to repeat the same information twice.”

United States v. Washington, Case No. 23-7036, 2025 U.S.App. LEXIS 32550 (4th Cir. Dec. 12, 2025)

Hurts so Bad: If there is any recurring theme in Bureau of Prisons prisoner care, it’s the BOP’s consistent failure to give any credence to inmate health complaints, too often until it’s much too late to prevent permanent injury or death.

Troy Williams filed a compassionate release motion claiming that the Bureau of Prisons had failed to adequately treat his medical condition by not testing his blood enough to ensure the medicine was working and that lockdowns were preventing treatment.

The district court found that the BOP medical treatment may have been inadequate, but it wasn’t that inadequate. Just sort of inadequate, and not inadequate enough to warrant intervention. Last week, the 6th Circuit agreed.

The Circuit said that while the BOP provided a declaration from its Health Services clinical director, Troy provided no “expert medical testimony” to connect sporadic and inadequate blood testing with any harm to his health. The evidence showed that even during a period with less than the recommended monthly testing, his numbers remained within an acceptable range and his doctors did not adjust his drug dosage.“ Given the overall record, the 4th said, the district court did not clearly err in finding that the frequency of Williams’s blood testing did not present a “risk of serious deterioration” to his health.

Troy also argued that lockdowns were preventing the facility from adequately treating him, but his medical records showed only one blood test was missed. He cited a third-party investigation of the prison that reported that frequent lockdowns interfered with medical care. As the government points out, however, there is only one documented instance in Williams’s voluminous medical records of a lockdown interfering with his blood testing. The BOP’s declaration and medical records got more credit than the third-party report, a decision that the appellate court held was not clearly erroneous.

The suggestion that compassionate release movants may need their own expert witnesses to counter the BOP’s self-serving medical declarations is troubling, raising a financial bar to relief that not many people can afford to overcome.

United States v. Williams, Case No. 25-3241, 2025 U.S.App. LEXIS 32556 (6th Cir. Dec. 12, 2025)

~ Thomas  L. Root

Low Sentence Undoes § 2255 Prejudice – Update for December 9, 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.

LAWYER’S ERROR ON GUIDELINES NOT ALWAYS PREJUDICIAL, 11TH SAYS

In 2016, Cecil Buckner pled guilty to several Hobbs Act violations and 18 USC § 924(c) counts. The presentence report classified him as a Guidelines career offender because Cecil had two prior felony convictions for a controlled substance offense. The combined statutory minimum sentence for his § 924(c) convictions was 384 months. The PSR calculated a career-offender range of 535 to 572 months’ imprisonment. Without the career-offender classification, Cecil’s guideline range would have been 504 to 534 months.

At Cecil’s sentencing, no one objected to the PSR. The district court adopted it as its findings of fact and imposed a 414-month prison sentence, reducing it by 121 months because the § 924(c) mandatory sentence was so long that it amounted to an essentially life sentence.

Later, in a 28 USC § 2255 petition, Cecil argued that the PSR was wrong in classifying him as a career offender and that his lawyer had been ineffective for failing to object to the error. Without the mistake, Cecil says, the bottom of his Guidelines range would have been 31 months lower.

It has always been generally accepted that an incorrect Guidelines calculation is enough to show § 2255 prejudice, that is, a reasonable probability of a different outcome. But last week, the 11th Circuit said this presumption is not carved in stone.

The Circuit held that the application of an erroneous Guideline range may not be dispositive on the prejudice prong when the district court gives “a detailed explanation… mak[ing] it clear that the judge based the sentence… on factors independent of the Guidelines.” Here, the district court sentenced Cecil based on factors independent of his career-offender classification, imposing a sentence of 414 months of imprisonment, only 30 months more than the mandatory 384 months for the two § 924(c)s.

Because the district court arrived at Cecil’s sentence by balancing his life expectancy with the “terror” and “fear” that he inflicted upon his victims, the 11th held, Cecil had “not established a reasonable probability that his sentence would have been different if counsel had objected to his career-offender classification.”

Buckner v. United States, Case No. 24-10001, 2025 U.S.App. LEXIS 31479 (11th Cir., December 3, 2025)

~ Thomas L. Root

You Should Have Told Me That… Update for October 24, 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.

IT WASN’T BRAIN SURGERY…

Nita Patel operated companies offering mobile diagnostic test services at a physician’s office. To pay for the services, Medicare required a licensed physician on staff to sign off on the tests.

When applying to Medicare for approval to do one kind of neurologic diagnostic testing, Nita’s husband falsely represented that a licensed neurologist would supervise the tests. Based on the representation, Medicare approved the companies as providers of the specialized test. The companies started testing with one of the owners – who was not a licensed doctor – forging a physician’s signature on the tests.

The companies made over $4 million from the scheme.

People who pull such scams shouldn’t. If they do, they should keep their employees happy. A disgruntled Patel worker lodged a qui tam claim against the companies (a civil action in which, if the government wins a judgment, the person bringing the action gets a monetary reward).

The government looked at the claim and smelled a rat. It then indicted the Patels. A day after the husband and wife pled guilty in 2016, the Government took over the qui tam action from the employee, asserting a False Claims Act cause of action. 

There’s a problem with guilty pleas beyond the obvious prison, fines, forfeitures and reputational harm. Such a plea can be used against the defendant in a civil action. The Patels’ guilty pleas pretty much made their liability in the qui tam action ‘game, set and match.’

Nita filed a 28 USC § 2255 motion, claiming her lawyer rendered ineffective assistance because he never told her that her guilty plea could be used against her in a False Claims Act lawsuit. Comparing her case to Padilla v. Kentucky –  a 2009 Supreme Court decision holding that defense attorneys have a duty to advise their defendant-clients of the immigration consequences of a guilty plea – Nita argued that counsel had a duty to advise her of all collateral consequences of pleading guilty, including the risk of civil liability.

C’mon, people. The notion that if you rip off the government, you might be forced to pay the government back is not such a hard idea to wrap your head around. Likewise, if you swear under oath that you committed a crime in doing so – necessary if you’re pleading guilty – you shouldn’t be shocked if another court relies on that admission.

Last week, the 3rd Circuit ruled against her.

The 3rd held that even though Nita had finished her prison sentence and supervised release term, she still met § 2255’s “in custody” requirement for bringing a motion because she faced substantial collateral civil consequences from her conviction.

That hardly mattered, however, because the Circuit held that Padilla does not address whether the “distinction between direct and collateral consequences [should] define the scope of constitutionally ‘reasonable professional assistance’ required under Strickland.” Rather, deportation stands alone among non-criminal consequences requiring proper attorney advice as a matter of the 6th Amendment.

It probably would have been a good idea for defense counsel to talk about civil liability flowing from admitting criminal guilt to a $4 million scam.  But counsel’s failure to do so was not ineffective assistance under the 6thAmendment.

Patel v. United States, Case No. 23-2418, 2025 U.S. App. LEXIS 27085 (3d Cir. October 17, 2025)

~ Thomas L. Root

Sometimes You Can Speak For Yourself, 6th Circuit Says – Update for October 16, 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.

CATCH-22

When Derek Riley pled guilty in 2016 to conspiracy to distribute controlled substances, his Guidelines Criminal History Category was III yielded an advisory sentencing range of 135 to 168 months. The district court sentenced him to 160 months.

In 2023, Amendment 821 to the Sentencing Guidelines retroactively lowered some criminal history points, including Derek’s. His new Guideline sentencing range was 121 to 151 months. A public defender representing him in the resentencing stipulated with the government to a 144-month sentence, which the court imposed.

Derek was not happy with the new sentence and filed a document he wrote himself called a “Motion for Reconsideration.” In it, he stated that his attorney had agreed to the stipulation as to his sentence without his knowledge or consent and that, therefore, the district court should reconsider and entertain the arguments he wanted to make in favor of a “time-served” sentence. The district court denied the motion on the grounds that Derek had a lawyer and thus was not allowed to file pro se motions under the policy prohibiting “hybrid” representation. The court told Derek that if he wanted to file a motion for reconsideration claiming that his lawyer had gone off the reservation, he should have his lawyer file it for him.

Joseph Heller’s “Catch-22” was this: If a World War II bomber airman wanted to avoid flying combat missions over Europe by claiming he was insane, he had to apply for the exemption. But the combat missions were so dangerous – only 25 pct of aircrews survived the 25 missions they were to fly before being relieved – that claim madness to get out of combat was interpreted as proof of sanity, so the application would be denied. “Catch-22” now describes a paradoxical situation from which there is no escape.

Thinking that the court’s instruction that only his lawyer could file a motion claiming his lawyer had agreed to something without his client’s approval veered very close to being a “Catch-22,” Derek filed a pro se notice of appeal.

Last week, the 6th Circuit agreed with Derek. The Circuit acknowledged that the rule against hybrid representation was a good one, because usually, whether to file certain motions and what to say in those motions are decisions for counsel, not the defendant.

“But cases like this one,” the 6th held, “present a materially different landscape. Here, the court was not simply presented with a disagreement over strategic choices made by the attorney nor an instance of nonspecific dissatisfaction. Instead, the court was faced with the defendant’s specific allegation that his counsel made a decision affecting the overarching aims of the representation without his knowledge or assent. A defendant must be permitted to make important decisions as to the direction of his case regardless of whether he is represented. A lawyer may not override a defendant’s decision to accept or reject a plea offer or disposition offered by the government because ‘decisions regarding the exercise or waiver of basic trial rights are of such moment that they cannot be made for the defendant by a surrogate…’ Where a defendant alleges conduct that amounts to such a violation, his allegations, if true, point to a breakdown in proper representation. His dissatisfaction and disagreement with his counsel should, therefore, be an apparent and pressing concern, triggering the district court’s obligation to investigate.”

The Circuit observed that the “clear thrust of the motion was that Riley wanted to proceed pro se because his counsel had agreed to a specific disposition of his § 3582 motion (a revised sentence of 144 months) without his consent. The district court then had an obligation to address that allegation directly in deciding Riley’s pro se motion.”

United States v. Riley, Case No. 24-1287, 2025 U.S.App. LEXIS 26350 (6th Cir. October 9, 2025)

~ Thomas L. Root

Lawyers Can Be Wrong But Still Be Good, 7th Says – Update for October 2, 2025

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WRONG DOESN’T MEAN INEFFECTIVE, 7TH CIRCUIT SAYS

Otis Elion pleaded guilty to distributing meth in 2017. The district court held that he qualified as a Guidelines Chapter 4B “career offender.” Otis’s attorney did not object, because after researching whether his prior convictions qualified as predicate offenses for career offender, she concluded that challenging that sentencing enhancement would fail.

In his 28 USC § 2255 petition, Otis argued his lawyer provided ineffective assistance under Strickland v. Washington by not challenging his “career offender” status. The district court agreed that he was prejudiced because he really didn’t qualify as a “career offender,” but that his lawyer – although wrong – was not ineffective.

With several prior drug convictions, Otis may have been a “career offender” under USSG § 4B1.1(a). The drug convictions might have been considered to be “controlled substance offenses, “defined as federal or state offenses that “prohibits the manufacture, import, export, distribution, or dispensing of a controlled substance (or a counterfeit substance)” or possession with intent to engage in those actions, punishable by imprisonment for a term exceeding one year.”

One of Otis’s priors was a 2006 federal conviction for distribution of crack cocaine. Before that was a 2000 conviction for delivery of a look-alike substance. The oldest was a 1999 conviction for delivery of a look-alike substance within 1,000 feet of public housing property. The Presentence Report concluded that those convictions qualified Otis for career offender.

His attorney reached the same conclusion, so she did not object to the application of the enhancement at Otis’s sentencing. Instead, she argued Otis ‘s health and life circumstances justified a mitigated sentence. The district court sentenced Otis as a “career offender” to 167 months.

To Otis, neither his 1999 nor his 2000 state convictions was controlled substance offense because look-alike substances made the Illinois statute broader than the Guidelines, and his lawyer’s failure to make that argument violated his 6thAmendment right to effective assistance of counsel. Using the modified categorical approach, the court agreed the Illinois use of “look-alike” substance made it different from the Guideline’s use of counterfeit substance.

Otis’s attorney had wrongly concluded that “counterfeit” and “look-alike” were a categorical match. But the 7th Circuit said last week that a defense attorney does not need to forecast changes in the law. “Failure to object to an issue that is not settled law within the circuit is not unreasonable by defense counsel… A defense attorney’s choice not to make a potentially meritorious argument is not automatically deficient performance, even if it stems solely from a legal error.” 

Strickland holds that the “proper measure of attorney performance remains simply reasonableness under prevailing professional norms,” the 7th said. Strickland necessarily permits mistakes that are reasonable. Only when the defense attorney’s error is so appalling that he can no longer be considered “counsel” for his client is his performance deemed deficient… The giving of legal advice that later is proven to be incorrect, therefore, does not necessarily fall below the objective standard of reasonableness.

If an attorney declines to make an argument that no court has accepted and no other attorney has made, yet which later succeeds, it is doubtful the attorney’s omission was unreasonable under prevailing norms of practice. Otis’s lawyer did the necessary work, the 7th observed. “She researched the categorical approach arguments, found the applicable caselaw, and analogized that precedent to Otis’s case. When the caselaw provided no answer, she used statutory interpretation and relied on her extensive experience. She just reached a different conclusion than the Circuit did —a  conclusion on which reasonable minds could disagree.”

Elion v. United States, Case No. 24-3014, 2025 U.S. App. LEXIS 24770 (7th Cir. September 24, 2025)

~ Thomas L. Root

Failure to Anticipate Is Not Ineffective Assistance – Update for September 12, 2025

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Should Have Seen That Coming

Tyree Neal pled guilty to conspiracy to distribute cocaine in violation of 21 USC §§ 841(a)(1), (b)(1)(C), and 846. At his sentencing, the district court found that Ty’s prior Illinois cocaine conviction supported a recidivism enhancement under § 841(b)(1)(C) that raised his maximum sentence from 20 years to 30 years. The district court hammered him with 30 years.

Two years after Tyree lost his appeal, the 7th Circuit held in United States v. Ruth that under the “categorical approach,” because Illinois’s definition of cocaine is broader than the federal definition, an Illinois conviction for cocaine delivery could not support a recidivism enhancement under 21 USC § 841(b)(1)(C). This meant that if Ty were sentenced today, his maximum sentence would be 20 years.

Ty filed a 28 USC § 2255 habeas corpus motion arguing that his appellate, sentencing, and plea attorneys were all constitutionally deficient because they failed to anticipate the argument that ultimately won in Ruth. Ty claimed they should have seen it coming and raised it in his case.

The district court denied his § 2255 motion. Last week, the 7th Circuit agreed.

The Circuit said the proper inquiry is “an objective assessment of counsel’s performance considering the options available to the defense.” Considering his appellate attorney, the 7th agreed that “looking back, it is fair to say the Ruth argument was stronger than those appellate counsel made (if that is not already apparent from the outcome of Ruth compared to Neal’s direct appeal). But we cannot conclude the Ruth argument was “clearly stronger” at the time of Neal’s appeal.

“A significant obstacle to comparison is that the arguments aimed at different goals. As an appellate lawyer must, counsel curtailed the number of issues by focusing on Neal’s conviction. If her arguments prevailed, Neal would have had a second opportunity for trial and acquittal. A successful Ruth challenge would have left Neal with a 20-year sentence. Those different ends do not affect the likelihood of success for their different means, but they would influence an attorney’s professional judgment about the “strongest” issues for appeal. Although we can imagine situations where an argument against a defendant’s sentence is strong enough that it must be raised even if in the alternative, appellate attorneys are not always required to pick issues with a higher likelihood of success but a lower reward.”

“Holding that appellate counsel provided ineffective assistance would thus encourage a kitchen-sink approach to advocacy,” the Circuit said, “the implicit logic being that she should have made the Ruth argument in addition to the issues she raised, not instead. Would an attorney still think we would find the Ruth argument persuasive if she knew it shared a limited page-count with Neal’s plea arguments? “As for sentencing counsel, the 7th said, he did what Ty asked him to, attackng the enhancements for use of violence, obstruction of justice, and reckless endangerment. After Neal provided “the names of a number of witnesses that he wanted counsel to interview,” counsel retained an investigator to interview those witnesses, subsequently spoke with several, and subpoenaed them to appear at Ty’s sentencing. Counsel also negotiated a plea deal that, if the court had followed it, would have given Ty the same 20-year sentence that a Ruth issue would have given him.

The Circuit said,

After Ruth, we can comment that sentencing counsel’s attempts to lower Neal’s offense level and convince the district court to exercise its discretion leniently were not the best possible approach to reducing Neal’s exposure. But it is difficult to establish ineffective assistance when counsel’s overall performance indicates active and capable advocacy.

Neal v. United States, Case No. 23-1722, 2025 USApp LEXIS 23018 (7th Cir. Sept 5, 2025)

United States v. Ruth, 966 F.3d 642 (7th Cir. 2020)

~ Thomas L. Root

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

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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

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

Fly The Friendly Skies of § 2255 Prejudice – Update for November 7, 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.

PREJUDICE FLIES FIRST CLASS

Kay Ellison and a friend started their own airline, Direct Air. Owning an airline worked for Sir Richard Branson (Virgin Atlantic) but not for Donald Trump (Trump Shuttle). It didn’t work for Kay, either.

trumpshuttle241107Under federal regulations, a charter airline like Direct Air has to keep money passengers pay for tickets in an escrow account until they take the flight. But when Direct Air’s money got tight, Kay tapped the escrow account by faking some records in order to keep the planes flying. Those things seldom work, and they didn’t work for Kay: she and her co-owner were charged with wire fraud and bank fraud conspiracy.

At trial, Kay did not present a defense, and the jury obligingly convicted her on all counts.

In a 28 USC § 2255 post-conviction motion, Kay claimed her lawyer had rendered ineffective assistance, a 6th Amendment violation and a first-class ticket to a new trial. Kay said her lawyer wrongly told her that if she declined to testify, she could not present other witnesses or evidence. Ellison believed him, and did not put witnesses and records before the jury. She argued this advice prejudiced her defense by depriving her of the opportunity to contest key portions of the Government’s case – she had lobster thermidor to serve the jury, but they got a little packet of peanuts instead.

The District Court concluded that even assuming Kay could prove her attorney told her something as wrong-headed as what she claimed he said, she could not show prejudice.

airposter1241107An argument of ineffective assistance made on a § 2255 motion has two components. First, the attorney must have performed deficiently. Second, the § 2255 movant must show that there is a reasonable probability that, but for counsel’s errors, the result of the proceeding would have been different.

Here, the District Court focused on prejudice first. Assuming the lawyer told her such a bone-headed thing, the court asked “whether there is a reasonable probability… that if Kay had testified herself and presented the testimony of her proposed witnesses, the jury would have acquitted” her. The judge concluded that “with or without the proposed witness testimony… evidence of Kay’s involvement in running Direct Air makes it unlikely the jury would conclude she was not involved” in the withdrawal scheme.

Kay argued that her right to testify was so fundamental that the correct prejudice test was not whether the jury would have acquitted her. Instead, the test should be a “process-based” inquiry. She likened her case to § 2255 motions alleging lawyer ineffectiveness in counseling a defendant of accepting a plea offer: In such cases, the courts have judged prejudice by asking whether or not the defendant would have taken or rejected a plea deal, not whether the defendant could have prevailed at trial. Kay argued the proper test here should be a similar one, whether – if her lawyer had given her good advice – she would have exercised her right to testify.

airposter2241107Last week, the 3rd Circuit grounded Kay’s process-based prejudice flight of fancy. In a decision that is a must-read primer on prejudice, the Circuit explained that “actual prejudice” – proof that the outcome is reasonably likely to have been different – “is required where the alleged error occurs within a judicial proceeding that is otherwise presumptively reliable. That must include right-to-testify claims like [Kay’s], because the error in those cases (i.e., failing to present testimony from the defendant or other defense witnesses) occurs during the presentation of the case to the jury and may therefore be quantitatively assessed in the context of other evidence presented in order to determine what effect, if any, it had on the jury’s verdict.”

Kay, the 3rd ruled, “needed to show a reasonable probability that, but for counsel’s errors, she would have exercised her trial rights, and that doing so would have changed the result.” She could not, leaving her § 2255 stranded at the gate.

Ellison v. United States, Case No. 22-2169, 2024 U.S. App. LEXIS 27494 (3d Cir., October 30, 2024)

– Thomas L. Root