Bad Advice Amounts To Ineffective Assistance Of Counsel, High Court Rules

Ineffective assistance of counsel is the most common claim presented in a 28 U.S.C. § 2255 motion.

A § 2255 motion is used by federal prisoners to seek relief from their conviction or sentence. Under section 2255, a federal prisoner may move to vacate, set aside, or correct their sentence if it was (1) imposed in violation of the constitution; (2) imposed in violation of the laws of the United States; (3) the sentence exceeds the maximum authorized by law; (4) the conviction or sentence was imposed without jurisdiction; or (5) the sentence is otherwise subject to collateral attack.

ineffective assistance of counsel

Ineffective Assistance of Counsel

There are strict time frames for seeking 2255 relief. In general, a 2255 motion must be filed within one year after a prisoner’s case becomes “final.” 28 U.S.C. § 2255(f)(1). If no appeal is taken after sentencing, the motion must be filed one year and 14 days after the entry of judgment. If the defendant files a direct appeal, the 2255 motion must be filed one year after: (1) the date the appeals court enters its opinion plus 90 days, if review with the Supreme Court is not sought; (2) the date the appeals court denies rehearing plus 90 days, if review with the Supreme Court is not sought; or (3) the Supreme Court denies certiorari.

To prove ineffective assistance of counsel, a defendant must demonstrate by a preponderance of the evidence that (1) his or her counsel rendered deficient performance and (2) the defendant was prejudiced by those errors or omissions. Prejudice is typically shown through a reasonable probability of a different outcome but for counsel’s deficient performance.

The Supreme Court Refines The "Prejudice" Inquiry For Guilty Plea Ineffective Assistance of Counsel Claims

This past Friday, the Supreme Court decided an extremely important case involving guilty plea ineffectiveness. The case is called Lee v. United States, 2017 WL 2694701 (2017).

Jae Lee moved to the United States from South Korea when he was 13.  He worked in Tennessee running two restaurants. Over 35 years, he never returned to South Korea. Lee, however, never applied for citizenship and only had lawful permanent residence.

In 2008 Lee was arrested and charged with possession with intent to distribute ecstasy. Lee pled guilty pursuant to a plea agreement after his attorney assured him that he would not be deported if he pled guilty. He received a year and a day in prison.

However, after arriving in the BOP, Lee learned that he had been misadvised. Lee had pled guilty to an “aggravated felony,” which except in limited situations requires deportation. So Lee filed a 2255 motion arguing that his attorney was ineffective for misadvising him about the deportation consequences of his plea.

A magistrate judge recommended that Lee be granted relief after receiving testimony from Lee and his former lawyer. It was unequivocal that Lee had been misadvised. Lee’s lawyer admitted this. Further, Lee’s lawyer testified that he would have recommended that Lee go to trial if he had known that Lee would be deported as a result of his plea. Thus, per the magistrate, Lee's lawyer had rendered ineffective assistance of counsel.

Nevertheless, the district judge rejected the magistrate’s recommendation. According to the district court, Lee was not prejudiced by his lawyer’s misadvice because there was virtually no chance that Lee would have been acquitted if he would have gone to trial.

The Sixth Circuit upheld the lower court's decision on appeal. According to the Sixth Circuit, 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.”

Lee appealed to the Supreme Court. In an opinion by Chief Justice Roberts, the Supreme Court reversed.

Justice Roberts began by drawing a distinction between claims of prejudice arising from “attorney error during the course of a legal proceeding” versus “deficient performance [that] arguably led not to a judicial proceeding of disputed reliability, but rather to the forfeiture of a proceeding itself.” In the former situation, prejudice is most typically shown through “a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different.”

In the latter situation, as Chief Justice Roberts 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.’"

The Court recognized that sometimes a defendant will have to show “that he would have been better off going to trial.” But that showing is only required “when the defendant's decision about going to trial turns on his prospects of success and those are affected by the attorney's error—for instance, where a defendant alleges that his lawyer should have but did not seek to suppress an improperly obtained confession.”

In Lee’s case, according to the Chief Justice, “the error was instead one that affected Lee's understanding of the consequences of pleading guilty.”

The Government argued for “a per se rule that a defendant with no viable defense cannot show prejudice from the denial of his right to trial.”

However, the Court held that the adoption of a categorical rule would be inappropriate because (1) claims of ineffective assistance of counsel require a “case-by-case examination” of the “totality of the evidence”; and (2) the relevant inquiry “focuses on a defendant's decisionmaking, which may not turn solely on the likelihood of conviction after trial.”

The Court recognized that defendants with little to no chance of success at trial will often have a hard time proving that they would have gone to trial instead of pleading guilty. But this is not because of the possible outcome of the trial, but because of how the prospect of success would have affected the defendant’s decision to plead.

Nevertheless, the Court recognized that sometimes the potential consequences of going to trial versus pleading guilty can both be bad. According to the Court, “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.”

The Court was careful to make clear that “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.”

As applied to Lee, the Court found that Lee had demonstrated a reasonable probability that he would have gone to trial had he been properly advised by his counsel.

“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 judgment of the Sixth Circuit affirming the denial of 2255 relief was accordingly reversed. Lee v. United States, 2017 WL 2694701 (2017).

Plain Language Takeaways About Ineffective Assistance Of Counsel Under Lee

While Lee may have been decided in the context of bad advice about deportation consequences, the impact of this decision will be felt much more broadly. That is because defendants frequently assert that they would have gone to trial but for misadvice by their lawyer.

Lee is extremely important because it makes clear that the prejudice inquiry in the context of this kind of ineffective assistance of counsel claim must focus on the decisionmaking of the defendant. Sometimes the prospects of winning at trial will be slim, but compared to a 20 or 30 year sentence, the chances of losing at trial versus a possible acquittal may have been worth it.

28 U.S.C. § 2255 Form And Rules For Claims Of Ineffective Assistance of Counsel

If you are looking for a 28 U.S.C. § 2255 motion form, you can access that here: 28 U.S.C. 2255 form.

The Rules Governing 28 U.S.C. § 2255 Proceedings can be accessed here: Rules Governing 28 U.S.C. 2255 Proceedings.

The federal statute 28 U.S.C. § 2255 is accessible here: 28 U.S.C. § 2255.

About Brandon Sample

Brandon Sample is an attorney, author, and criminal justice reform activist. Brandon’s law practice is focused on federal criminal defense, federal appeals, federal post-conviction relief, federal civil rights litigation, federal administrative law, and the Freedom of Information Act (FOIA).


  1. Sandra K. Boettcher on April 6, 2018 at 7:53 am

    My husband of 34 yrs, Ronald Tingle #12994-028, was sentenced to 25 yrs for small-time, non-violent drug charges. Case #15-cr-00023, Southern District of Indiana. Due to his age, 62, he went to trial. Found guilty on all counts. They do not play fair. Judge requested prosecutor to drop 851 and they refused. Direct Appeal filed immediately (17-1604). Oral arguments heard but case was recently denied, as was the rehearing enblanc. A Writ of Certiorari was filed 3-2-2018 (17-7982). We are looking for help with 2255. Please help us.

  2. Lisa casey kiser on November 8, 2018 at 1:07 pm

    I was charged in state court with perjury bc i did not anwser a question from a magiatrate. I had no idea by not anwsering that it was infact breaking the law. The police officer charged me 2 weeks later .i was in jail when served. I was in hand cuffs. My miranda was not read and the cop illegally recorded me on his cell phone saying I wasn’t in my right mind i was confused. I did not know i lied until the police told me i lied.: this ended up violating my federal probation. My lawyer refused to suponea any witnesses on ny behalf. He wanted to with drawl from my case but he said the judge wouldnt allow it.he said i did not pay him his full fee. He would not.introuduce my medical records bc the probation officers and court said they were all altered and fake. He did not ask the questions to the PO i told gim to ask. I have 4yr old special needs child. I am his only care taker and provider. He will go to foster care. I was sentenced to 24 mo in prison. I filed my appeal. I need help filing motion for stay of imprisonment until appeal is heard and 2255 bc of the fact once my sin enters foster care i lose my rights and can not get him back.

  3. Rebecca on July 9, 2020 at 8:34 pm

    Three years ago my fiance was charged with forgery and pled down to felony uttering after he was with his ex when she signed one of the grandmother’s checks. He served 18 months, was released on home incarceration with weekly drug testing for five months, then judge’s parole. He and i then met and he would visit me at my home then return to his grandmother’s where he had been assigned to reside. He got stuck out of town for two weeks and was arrested for absconding probation. In his psi they lisred 5 violations, one of which was “apparently defendant no longer resides at the home and has absconded.” Another was listed as a diluted drug test, which he had been told was negative, but “looked watered down”. The last hearing was june 19th, when the lawter requested a continuance pending vote on his eligibility into drug court. The lawyer is on this committee for drug court, and he was denied. Today (7-9-2020) was his final sentencing hearing. I previously contacted the lawyer regarding my being a witness to the fact he never lived elsewhere, only visoted me, and he had prior to that asjed to sign a release so that i may have informatoon regarding his case. She refused both requests. Today it was fpund he will serve the remainder of his 1-10 sentence.

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