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

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

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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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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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

The Fine Print Counts In A Deal With the Devil – Update for February 20, 2024

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‘SHUT UP AND SIGN’ LEADS TO A LOT OF BUYER REMORSE

About 95% of all federal indictments end with a plea agreement where the defendant agrees to take a guilty plea in exchange for government promises that often seem evanescent if not illusory. If I had a dime for every prisoner who has told me that he or she only signed because defense counsel said to, I would be writing this on the beach of my private Caribbean island instead of at a desk looking out at February snow in Ohio.

plea161116Two cases decided last week remind all prisoners – including those who have already signed their plea agreements – that in a plea agreement, every promise counts. A defense attorney’s disservice to the client is never greater than when he or she rushes them into signing a “good deal” without first painstakingly walking the defendant through every provision and explaining it in detail.

Eric Rudolph (remember him?) decided to express his political views by blowing up Olympic venues and abortion clinics. The innocents he slaughtered in the process were just icing on his demented cake. After five years on the lam, Eric was caught dining out of a dumpster in Murphy, North Carolina, and was later convicted of one 18 USC § 844(i) arson offense and five companion 18 USC § 924(c) counts for using a firearm (bombs studded with nails qualify under the statute as “firearms”) in the commission of the arson.

Eric’s approach to the plea agreement was unrepentant. He said he had “deprived the government of its goal of sentencing me to death,” and that “the fact that I have entered an agreement with the government is purely a tactical choice on my part and in no way legitimates the moral authority of the government to judge this matter or impute my guilt.”

Uh-huh. Eric’s statement brings to mind old Gus McRae (Lonesome Dove) addressing outlaw Dan Suggs, who was about to be executed with his brother but expressed only hatred and contempt:

Gus McCrae: I’ll say this, Suggs; you’re the kind of man it’s a pleasure to hang. If all you can talk is guff, you can talk it to the Devil.

supermaxcell240220I’m no fan of mandatory life sentences and even less of the death penalty, but it’s amazing how malleable our principles can be when we’re punched in the face with pure-D evil. Eric undeservedly got a life sentence, which he’s spending in the mountains of Colorado (although he never gets to see them from his concrete cell at ADX Florence).

As part of the plea deal he was proud of for depriving the Feds of the death penalty, Eric waived the right to collaterally attack his sentence in any post-conviction proceeding, including under 28 USC § 2255. But because of what the Court disapprovingly calls “the evergreen litigation opportunities introduced by the categorical approach” to § 924(c) litigation,” Eric – who has apparently decided that freedom some day isn’t such a bad goal – has filed two § 2255s so far. Last week, the 11th Circuit turned down his second one as barred by the plea agreement and, in so many words, told Eric to enjoy his place in the mountains for the rest of his life.

In the last few years, courts have applied the Supreme Court’s “categorical” approach to determining whether an offense is a “crime of violence” within the meaning of 18 USC § 924(c)(3)(A), that is, “an offense that is a felony and has as an element the use, attempted use, or threatened use of physical force against the person or property of another.” Even Eric’s district court agreed that after the Supreme Court’s decision in United States v. Davis, his arson offenses were no longer crimes of violence under the federal statute (because one can be convicted of arson for burning down his or her own property). But that didn’t matter, the district court said, because Eric had given away his right to bring a § 2255 motion to correct the error.

Last week, the 11th Circuit agreed. It held that “a plea agreement is, in essence, a contract between the Government and a criminal defendant. And because it functions as a contract, a plea agreement should be interpreted in accord with what the parties intended. In discerning that intent, the court should avoid construing a plea agreement in a way that would deprive the government of the benefit that it has bargained for and obtained in the plea agreement.”

Eric’s plea deal, the 11th said, contained the common waiver of the right to bring a collateral attack on his sentence. But Eric argued that the plea deal only prohibited collateral attacks on the sentence, while his collateral attack was on the § 924(c) convictions.

dumpsterfire249220Eric’s argument was a dumpster fire, the Circuit said. “The text of 28 USC § 2255, the history of that same statute, and the habeas corpus right that it codified, all point in the same direction: 2255 is a vehicle for attacking sentences, not convictions.” Starting with the origins of English habeas corpus through the codification of 2255 up to last summer’s Supreme Court Jones v. Hendrix decision (where SCOTUS said “Congress created 2255 as a separate remedial vehicle specifically designed for federal prisoners’ collateral attacks on their sentences”), the 11th concluded that the history, the plain text of the statute “shows the same, as does Rudolph’s requested relief… [His] motions are collateral attacks on his sentences, so his plea agreements do not allow them.”

Winning his § 2255 would have been a huge deal for Eric. The 18 USC § 844(i) conviction carries a maximum 10-year sentence. Each of the § 924(c) convictions carries a maximum of life. Had Eric been allowed to bring the § 2255, he would have gone from his concrete cell straight to walking the streets (something most of his victims would never enjoy again).

*     *     *

Meanwhile, over in Louisiana, Keesha Dinkins – a front-office worker at Positive Change healthcare clinic – was swept up in a Medicaid billing fraud. She didn’t make a dime from the fraud beyond her normal salary, but her lawyer had her sign a plea agreement for 24 months and restitution of $3.5 million.

positivechange240220Despite the deal she made, she argued that she should not be on the hook to share the restitution equally with Positive Change’s owner (who got a lot more time than she did). Last week, the 5th Circuit told her that it was Positive that it would not Change her restitution:

The criminal justice system in this country relies on plea agreements to provide efficient resolutions to criminal cases. Indeed, over 95 percent of federal criminal cases are resolved without trial. It would undermine the principle that plea bargains are contracts to hold that a party can agree to a specific amount of restitution, supported by record evidence, and then in the next breath, challenge an order imposing that exact amount of restitution.

The 5th observed that her plea agreement provided that “Dinkins — not Positive Change — was responsible for the $3.5 million loss.” That is how the judgment will remain.

Rudolph v. United States, Case No 21-12828, 2024 U.S. App.  LEXIS 3278 (11th Cir., February 12, 2024)

United States v. Johnson, Case No 22-30242, 2024 U.S. App. LEXIS 3487 (5th Cir., February 14, 2024)

– Thomas L. Root

Bad Advice Kills ‘No-Brainer’ Plea Deal, 10th Circuit Says – Update for January 26, 2024

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SIX MINUTES OF BAD ADVICE COST DEFENDANT AN EXTRA 14 YEARS

clockwatcher190620Jonathan Kearn was indicted on three counts alleging he possessed some unsavory and illegal photos of his own children. He was looking at a 30-year sentence when the government threw him a lifeline: it offered him a Rule 11(c)(1)(C) plea deal with a fixed 10-year sentence in exchange for a guilty plea to just one of the three counts.

Most plea agreements specify that, while the government and defendant may anticipate the Sentencing Guidelines will recommend a sentence within a certain range, the court is not bound by their anticipations and may impose whatever sentence it believes is appropriate. Federal Rule of Criminal Procedure 11(c)(1)(C), however, lets the government and criminal defendants lock the court into a binary choice: the judge may either accept the plea deal, which comes with an agreement that the defendant will get a certain sentence (or occasionally, a sentence within a certain range) regardless of what the Sentencing Guidelines recommend or the judge prefers.

If the court doesn’t like the sentence specified in the 11(c)(1)(C), it can reject the deal, at which time the defendant can walk away from the agreement and go to trial. So-called (c)(1)(C) pleas are popular with defendants because they provide certainty – defendants either receive the sentence they agreed to or they can withdraw their plea.

tooasy240126Anyone familiar with the draconian sentences usually imposed in child pornography cases would see acceptance of the (c)(1)(C) offer made to Jon as a “no-brainer.” But not Jon’s lawyer. After exhaustively counseling his client about the (c)(1)(C) plea for all of six minutes, learned counsel convinced Jon to reject the offer and proceed to trial. You can guess the end: Jon was convicted on all three counts and sentenced to 24 years in prison.

Jon filed a 28 USC § 2255 post-conviction motion, arguing his lawyer was constitutionally ineffective during the plea-bargaining phase. The district court found that counsel didn’t tell Jon that if the court accepted the plea agreement, he would be guaranteed a 10-year sentence but if the court rejected the plea agreement, he could withdraw the plea. In fact, the district court found counsel failed to explain anything at all about Rule 11.

The district judge granted Jon’s § 2255 motion and let him plead to the 10-year offer. This week, the 10th Circuit upheld the decision.

Jon’s hang-up was that he did not want to stand in open court and “personally describe the facts of his offenses – which involved his daughters – before his family and friends in open court.” Under Rule 11, “[b]efore entering judgment on a guilty plea, the court must determine that there is a factual basis for the plea.” This requirement is intended to ensure the accuracy of the plea through some evidence that a defendant actually committed the offense.

But Jon’s lawyer told him that he had to do that in order to accept the plea. This advice, the Court said, was absolutely wrong. “The defendant does not have to provide the factual basis narrative,” the appeals court said. Instead, “[t]he district court may look to answers provided by counsel for the defense and government, the presentence report, or… whatever means is appropriate in a specific case – so long as the factual basis is put on the record.”

dumblawyer180108Jon’s lawyer didn’t know this. The lawyer admitted that he “regularly advised his clients that they would have to admit the facts surrounding the offense… and didn’t know if Mr. Kearn would actually receive a 10-year sentence if he pleaded guilty.”

“In the plea agreement context,” the 10th ruled, “counsel has a critical obligation… to advise the client of the advantages and disadvantages of a plea agreement… Because counsel understated the benefits and overstated the burdens of the plea offer, Mr. Kearn could not make an informed choice about whether to accept it.”

The government argued that Jon could not show that his attorney’s bad advice prejudiced him because there was no evidence Jon would have taken the deal had his lawyer properly advised him. But the Court held that Jon “lacked the requisite information to weigh the options in front of him, and whatever desire he exhibited before trial is not dispositive of what he would have done if he were properly educated about the charges against him… We cannot rationally expect defendants to theorize contemporaneously about the decisions they would make if they were receiving different advice. If courts required this kind of evidence, no defendant could show prejudice.”

41475-Forever-Is-A-Long-TimeThe significant disparity between the 10-year sentence Jon was offered and the 24 years he got is very relevant to the prejudice analysis, the Court said. Jon “was not adequately informed that the district court would have been bound by the agreed-upon sentence. Thus, counsel improperly skewed his attention away from the sizeable sentencing disparity he faced in favor of the need for him to personally supply a factual basis… Sentencing disparity is strong evidence of a reasonable probability that a properly advised defendant would have accepted a plea offer, despite earlier protestations of innocence.”

United States v. Kearn, Case No. 23-3029, 2024 U.S. App. LEXIS 1471 (10th Cir. January 23, 2024)

– Thomas L. Root

‘You Agreed to an Unconstitutional Conviction,’ 2nd Circuit Says – Update for October 26, 2023

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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.

‘WAIVING’ JUSTICE GOODBYE

plea161116Resolving criminal cases by a plea deal is more than merely common. In the federal system, 98% of all cases end in a plea agreement where the defendant agrees to plead to one or more counts in exchange for the government usually agreeing to do not much at all. Sure, the defendant usually gets a 2-3 level reduction under § 3E1.1 of the Sentencing Guidelines for “acceptance of responsibility” by pleading guilty.

But often enough, the Government’s concessions are illusory while the defendant’s obligations become onerous.  One of the unexploded mines in the agreement is the waiver.  A defendant will waive the right to appeal the conviction or sentence and to bring a collateral attack on the conviction under 28 USC § 2255.

Such a waiver probably doesn’t seem that unfair, at least where waiving the right to appeal is concerned.  A plea agreement, after all, is supposed to end litigation. But what happens when the conviction to which a defendant agrees proves down the road to be unconstitutional?

hobbsact200218That happened to Derek Cook. Derek (like a number of co-petitioners in his case) pled guilty to conspiracy to commit Hobbs Act robbery – 18 USC § 1951(a) – and using a firearm in furtherance of a crime of violence – 18 USC § 924(c). In exchange for the government’s promise not to bring any more criminal charges, Derek agreed to waive a number of rights, including the right to collaterally attack the convictions and sentences under 28 USC § 2255.

But after the Supreme Court held in the 2015 Johnson v. United States case that the residual clause of the Armed Career Criminal Act was unconstitutionally vague, Derek filed a § 2255 motion in which he correctly argued that his conspiracy charge could no longer be a defined as a crime of violence supporting a § 924(c) conviction. The district court sat on the petition until SCOTUS agreed, definitively holding that, constitutionally, conspiracy could not be the basis for a § 924(c) in the 2019 United States v. Davis decision.

After that, the district court conceded that Derek’s conviction for using a firearm in furtherance of a crime of violence was unconstitutional. But that didn’t matter, the Court said, because Derek had waived his entitlement to a conviction that was constitutional by signing a plea agreement containing his commitment not to file a § 2255 motion.

Last week, the 2nd Circuit agreed. The Circuit wrote that “while we have not yet considered the precise question of whether collateral-attack waivers are enforceable in the wake of Johnson and Davis, we have made clear that such waivers are generally enforceable in the face of evolving judicial precedent… [T]he possibility of a favorable change in the law after a plea is simply one of the risks that accompanies pleas and plea agreements. This principle follows from the fact that plea agreements, like all contracts, allocate risk between the parties – and we are not free to disturb the bargain the parties strike.

pleadeal180104“The enforceability of a collateral-attack waiver,” the 2nd held, “turns on whether the petitioner’s plea was knowing and voluntary, not the nature of any subsequent legal developments… Petitioners counter that they have a due process right not to be convicted of a non-existent offense. But the question is not whether Petitioners have a right not to be convicted of a non-existent offense. It is whether Petitioners have a right to bring a collateral attack when, in exchange for valid consideration, they executed binding plea agreements admitting their criminal conduct and waiving their ability to challenge the resulting convictions. And on that score, our precedent is clear that ignorance of future rights is unavoidable and not a basis for avoiding a plea agreement.”

Cook v. United States, Case Nos. 16-4107 et al, 2023 U.S.App. LEXIS 27383 (2d Cir., October 16, 2023)

– Thomas L. Root

Government Can’t Walk Away From Plea Deal, 4th Says – Update for September 2, 2022

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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 DIDN’T AGREE THAT YOU COULD WIN’

The government prefers one-sided plea agreements, but – as a decision last month reminded us – sometimes the U.S. Attorney overreaches.

headsiwin220902(So why am I getting around to reporting this now, a month after the case was handed down? Vacation, county fair, August being August…)

Shelby Petties cut a deal in which the government agreed to drop two counts if he pled to having committed a crime of violence – kidnapping – while having failed to register as a sex offender. Shelby reserved the right to appeal on the ground that while he did the kidnapping, it is not categorically a crime of violence (COV).

Shelby appealed and won a ruling that kidnapping is not a COV. But when the case went back to the district court, the judge allowed the government to refile the dismissed charges against Shelby. The government’s view was that Shelby had agreed to plead guilty in order to appeal an issue that – if he won – the government could circumvent by undoing the agreement.

Shelby argued that the government’s view reduced the benefits he got from the plea agreement to zero. The 4th Circuit agreed.

“We give plea agreements greater scrutiny than we apply to ordinary commercial contracts,” the Circuit ruled, “because of the context: a defendant’s waiver of his constitutional right to trial, induced by the government’s commitments in the plea agreement.”

plea161116Here, Shelby gave up his right to go to trial on Count Two in exchange for the government’s promise to dismiss Counts One and Three and to “not further prosecute him for conduct constituting the basis” for the indictment. “The government entered into this agreement with full knowledge that Petties might appeal — and appeal successfully — his conviction on Count Two,” the Circuit held. “The possibility of a successful appeal was a contingency expressly contemplated by the parties and their agreement…”

United States v. Petties, Case No 21-4332, 2022 U.S.App.LEXIS 21158 (4th Cir., Aug 1, 2022)

– Thomas L. Root