So, I was sitting in a courtroom waiting for a case to be called and I noticed something disturbing. A guy standing at the podium, which happened to be next to my chair, was pleading guilty to a felony when the judge asked him, “Do you understand the terms of your plea agreement?” The guy paused and then asked his lawyer what something in the agreement meant. The lawyer whispered to him, “Don’t worry, we’ll fix it later on.” Happy with that answer, the guy told the judge he was “good” and was whisked away to serve his prison sentence.
Why is this disturbing? Because if the guy’s lawyer doesn’t fix whatever the problem was that made him hesitate before pleading guilty, he faces a rough road to undo that guilty plea. And he likely won’t succeed because he said — on the record in open court — that he understood the terms of his guilty plea. That will undoubtedly be used against him in any future challenge to his guilty plea, if he claims his lawyer’s empty promise induced him to plead guilty. What’s worse his guilty plea waived many of his rights, including the ability to challenge any errors made prior to the guilty plea.
He probably didn’t know all of this when he stood before the judge and said he understood his plea agreement. But it doesn’t matter. A guilty plea isn’t undone by a court for just any reason. The Supreme Court has established that a challenge to a guilty plea (with or without a plea agreement) must attack the “knowing and voluntary” nature of the plea. And if it’s a claim that counsel’s bad advice caused the plea, the challenge must be specifically about counsel’s bad advice to plead guilty, and not about the error itself. See Hill v. Lockhart (1985).
So this guy would not only need to show that counsel’s failure to follow through on his promise to fix the error had induced the plea, but that he would also have done something other than plead guilty the way he did, had he known counsel would drop the ball. Chances are, though, pleading guilty was still his best option despite his counsel’s errors. It’s a tough position.
In my book, Insider’s Guide: Attacking the Guilty Plea, I explain the different ways of establishing “prejudice” under the Supreme Court decision, Strickland v. Washington (1984), to undo a guilty plea infected by the ineffective assistance of counsel (IAC). The Supreme Court’s Strickland decision requires showing that (1) counsel’s advice was deficient, and (2) that the outcome would’ve been different absent counsel’s errors. However, the Supreme Court also made clear in subsequent cases that there’s a specific way of showing prejudice in the guilty plea context, depending on what counsel’s error was. Generally, there are three categories of Strickland prejudice when attacking a guilty plea: Bad advice to plead guilty (Hill v. Lockhart (1985)), bad advice to reject a plea offer (Lafler v. Cooper (2012)), and counsel’s failure to advise of a plea offer or the option to plead guilty at all (Missouri v. Frye (2012)).
I also wrote a series of columns for Criminal Legal News titled “Attacking the Guilty Plea,” where I went into detail on the knowing and voluntary standard, the stages of withdrawing a guilty plea, and the different IAC standards for the categories of guilty plea challenges noted above.
Most people are not aware that there are different standards for showing prejudice when attacking a guilty plea. To be successful in attacking your guilty plea, it is critical that you understand what category your claim falls under, and which standard you must meet.
Dale Chappell is the author of hundreds of published articles on the federal criminal justice system, and the Insider`s Guide series of federal post-conviction books. He is a consultant in federal post-conviction procedure and an authority on federal sex offense issues.