My Lawyer's Bad Advice Led Me to Plead Guilty. Can I Undo the Plea?

Possibly. If your lawyer's bad advice led you to plead guilty, you may be able to challenge the plea in a 28 U.S.C. § 2255 motion by showing you would have gone to trial with correct advice. In Lee v. United States, the Supreme Court made this kind of ineffective assistance of counsel claim easier to win, even for someone with little chance of winning at trial.

What a 2255 motion is

A 2255 motion asks the judge who sentenced you to throw out or correct your conviction or sentence. You can file one if your sentence:

1. violated the Constitution or federal law;
2. was imposed by a court without jurisdiction;
3. is longer than the law allows; or
4. is "otherwise subject to collateral attack."

28 U.S.C. § 2255(a).

The one-year deadline to file

In most cases, you have one year from the date your conviction becomes "final." 28 U.S.C. § 2255(f)(1). When is it final?

• No appeal: 14 days after the judgment is entered, when the time to appeal runs out under Federal Rule of Appellate Procedure 4(b)(1)(A). So the 2255 deadline is usually one year and 14 days after judgment.
• Appeal, but no Supreme Court petition: 90 days after the court of appeals rules (or denies rehearing), when the time to ask the Supreme Court for review runs out.
• Supreme Court petition denied: the date the Supreme Court denies review.

Section 2255(f) has three other start dates: when a government-created barrier to filing is removed, when the Supreme Court recognizes a new right and makes it retroactive, and when the facts behind the claim could have been discovered with due diligence. These are narrow. Do not count on them, and treat the one-year date as firm.

You also generally get only one 2255 motion. A second or successive motion needs permission from the court of appeals, and only newly discovered evidence or a new retroactive constitutional rule qualifies. 28 U.S.C. § 2255(h). So put every claim you have into the first motion.

What you must prove

You must prove two things by a preponderance of the evidence, meaning more likely than not:

1. Deficient performance: your lawyer's work fell below professional standards.
2. Prejudice: the error hurt you. Usually that means a reasonable probability of a different outcome without your lawyer's errors or omissions.

Jae Lee's case

On June 23, 2017, the Supreme Court decided an important case about bad advice and guilty pleas.

Jae Lee came to the United States from South Korea at age 13. He lived here for 35 years and never went back to South Korea. He ran two restaurants in Tennessee. He was a lawful permanent resident, but he never applied for citizenship.

In 2008, he was arrested and charged with possessing ecstasy with intent to distribute. His lawyer assured him he would not be deported if he pleaded guilty. Lee pleaded guilty under a plea agreement and got a year and a day in prison.

After he got to federal prison, Lee learned the advice was wrong. The offense was an "aggravated felony." Except in limited situations, that means deportation.

Lee filed a 2255 motion. He argued his lawyer was ineffective for giving him wrong advice about deportation. A magistrate judge heard testimony from Lee and his former lawyer. It was clear Lee had been misadvised, and the lawyer admitted it. The lawyer also said he would have told Lee to go to trial if he had known Lee would be deported. So the magistrate judge found ineffective assistance and recommended relief.

The district judge rejected that recommendation. The judge said Lee was not harmed because he had virtually no chance of being acquitted at trial.

The Sixth Circuit agreed. It said Lee could not show prejudice because "no rational defendant charged with a deportable offense and facing overwhelming evidence of guilt would proceed to trial rather than take a plea deal with a shorter prison sentence."

What the Supreme Court held

The Supreme Court reversed in Lee v. United States, 582 U.S. 357 (2017). Chief Justice Roberts wrote for the Court.

He began by separating two kinds of claims:

• Errors during a proceeding, like a trial. Here, prejudice usually means "a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different."
• Errors that cost you the proceeding itself. This is "deficient performance [that] arguably led not to a judicial proceeding of disputed reliability, but rather to the forfeiture of a proceeding itself."

Bad advice that leads to a guilty plea falls in the second group. As the Chief Justice wrote:

When a defendant alleges his counsel's deficient performance led him to accept a guilty plea rather than go to trial, we do not ask whether, had he gone to trial, the result of that trial 'would have been different' than the result of the plea bargain. That is because, while we ordinarily 'apply a strong presumption of reliability to judicial proceedings,' 'we cannot accord' any such presumption 'to judicial proceedings that never took place.' We instead consider whether the defendant was prejudiced by the 'denial of the entire judicial proceeding ... to which he had a right.'

When a defendant claims that his counsel's deficient performance deprived him of a trial by causing him to accept a plea, the defendant can show prejudice by demonstrating a 'reasonable probability that, but for counsel's errors, he would not have pleaded guilty and would have insisted on going to trial.'

Sometimes a defendant does have to show "that he would have been better off going to trial." But that is required only "when the defendant's decision about going to trial turns on his prospects of success and those are affected by the attorney's error." The Court's example: a lawyer who should have, but did not, try to suppress an improperly obtained confession.

Lee's case was different. "The error was instead one that affected Lee's understanding of the consequences of pleading guilty."

The government asked for "a per se rule that a defendant with no viable defense cannot show prejudice from the denial of his right to trial." The Court said no, for two reasons:

1. Ineffective assistance claims require a "case-by-case examination" of the "totality of the evidence."
2. The question "focuses on a defendant's decisionmaking, which may not turn solely on the likelihood of conviction after trial."

The Court admitted that a defendant with little or no chance at trial will often have a hard time proving he would have gone to trial. But that is because of how the odds would have affected his decision, not because of how the trial would have turned out.

Sometimes both choices are bad. "When those consequences are, from the defendant's perspective, similarly dire, even the smallest chance of success at trial may look attractive. For example, a defendant with no realistic defense to a charge carrying a 20–year sentence may nevertheless choose trial, if the prosecution's plea offer is 18 years."

But the Court added a limit. "Courts should not upset a plea solely because of post hoc assertions from a defendant about how he would have pleaded but for his attorney's deficiencies. Judges should instead look to contemporaneous evidence to substantiate a defendant's expressed preferences."

Applying these rules, the Court found a reasonable probability that Lee would have gone to trial with correct advice:

We cannot agree that it would be irrational for a defendant in Lee's position to reject the plea offer in favor of trial. But for his attorney's incompetence, Lee would have known that accepting the plea agreement would certainly lead to deportation. Going to trial? Almost certainly. If deportation were the 'determinative issue' for an individual in plea discussions, as it was for Lee; if that individual had strong connections to this country and no other, as did Lee; and if the consequences of taking a chance at trial were not markedly harsher than pleading, as in this case, that 'almost' could make all the difference. Balanced against holding on to some chance of avoiding deportation was a year or two more of prison time. Not everyone in Lee's position would make the choice to reject the plea. But we cannot say it would be irrational to do so.

The Sixth Circuit's judgment was reversed.

What Lee means if you pleaded guilty on bad advice

Lee was about bad advice on deportation, but its impact reaches much further. Defendants often say they would have gone to trial if their lawyer had advised them correctly.

Lee makes clear that the prejudice question for this kind of claim focuses on the defendant's decisionmaking. If bad advice led you to plead guilty, the question is what you would have done with correct advice. Sometimes the chance of winning at trial is slim. But compared to a 20- or 30-year sentence, taking that chance may have been worth it. A weak trial defense does not end the claim.

But you need proof from the time of your plea. Letters, emails, notes, and what you said in court can all matter. Gather your plea agreement, the transcript of your plea hearing, your judgment, and your docket number before you talk with a lawyer.

Forms and rules

• 28 U.S.C. § 2255 motion form
• Rules Governing Section 2255 Proceedings
• Text of 28 U.S.C. § 2255

For help with a 2255 motion, see 2255motion.com.

Facing a federal sentence? Book a consultation to talk it through with Brandon Sample.