Attacking the Guilty Plea Part III: Establishing Prejudice in the Guilty Plea Context

In my last column, we went over the general standard for showing ineffective assistance of counsel (“IAC”) in the guilty plea context under Strickland v. Washington, 466 U.S. 668 (1984).

In this column, we’ll go over the showing required to establish prejudice in the different categories of IAC regarding guilty pleas.

There are three main categories of IAC in the guilty plea context: (1) bad advice to plead guilty, (2) bad advice to reject a plea offer, and (3) the failure to communicate a plea offer or option to plead. And under each category, the Strickland standard applies, but how to establish “prejudice” to meet that standard varies by category.

The purpose of this column is to help you understand how to meet Strickland’s prejudice standard for whichever category your claim falls under.


By far, most IAC claims attacking the guilty plea will fall under the category where counsel’s bad advice induced the guilty plea. The prejudice showing required for this category of claims was announced by the U.S. Supreme Court in Hill v. Lockhart, 474 U.S. 52 (1985): “The defendant must show that there is a reasonable probability that, but for counsel’s errors, he would not have pleaded guilty and would have insisted on going to trial.”

Hill was the first Supreme Court case to apply Strickland in the guilty plea context (Strickland involved IAC during trial). The Court found that Hill hadn’t shown a reasonable probability of a different outcome (i.e., “prejudice”) because he never alleged he would’ve gone to trial had he received correct advice from his lawyer about his parole eligibility before pleading guilty.

Whether you need to show that you would’ve won at trial to show prejudice under Hill is another matter. The Supreme Court has recently clarified that success may have nothing to do with the decision to go to trial. In Lee v. United States, 137 S. Ct. 1958 (2017), the Court acknowledged that in some cases throwing a “Hail Mary” by going to trial might seem more rational than pleading guilty with a guaranteed losing outcome, like being deported. In Lee, the Court took yet another look at establishing prejudice after bad legal advice led to a guilty plea.

When Lee pleaded guilty, it all but guaranteed he would be deported. But by going to trial, he had the slim chance of an acquittal. The Government argued that Lee wouldn’t have gone to trial because he surely would have lost. But the Court countered that it would have been rational for Lee to go to trial: “But for his attorney’s incompetence, Lee would have known that accepting the plea agreement would have certainly led to deportation. Going to trial? almost certainly.” That “almost certainly” chance was enough to make it a rational choice for Lee to go to trial.

Calling the Hill prejudice inquiry “expanded” by Lee and several other Supreme Court cases applying Hill to guilty pleas, the Third Circuit summed up Hill’s standard this way: “The Hill inquiry did not involve examining the petitioner’s likelihood of success had he insisted on trial, but merely whether he would have gone to trial at all.” Velazquez v. Sup’t Fayette SCI, 937 F.3d 151 (3d Cir. 2019).

The lesson is that chances of success at trial matter little if it’s the only rational option available. Success at trial is just one of several factors on whether you would have not pleaded guilty but instead “insisted on going to trial” to show prejudice under Hill.

Do you have to prove you would have gone to trial, instead of some other option, to establish prejudice under Hill? What if you could have negotiated a better plea deal or taken some other option? Courts have accepted other alternatives in order to establish prejudice under Hill. See, e.g., United States v. Swaby, 855 F.3d 233 (4th Cir. 2013) (“but for his counsel’s erroneous advice, he could have negotiated a different plea agreement”); Rodriguez-Penton v. United States, 905 F.3d 481 (6th Cir. 2018) (collecting cases).

Besides counsel’s bad advice, the government’s misconduct could also provide grounds to establish prejudice under Hill. In a case where the government purposely withheld “stunning” evidence favorable to the defense, the court concluded that, “absent this misconduct, there was a reasonable probability that the petitioner would not have pleaded guilty but, rather, would have rejected the proffered plea agreement and opted for trial.” Ferrara v. United States, 456 F.3d 278 (1st Cir. 2006) (affirming grant of § 2255 motion).


What if your lawyer told you to reject a favorable plea offer because you had a great defense and could win at trial, only to find out he was dead wrong? The Supreme Court addressed this situation in Lafler v. Cooper, 566 U.S. 156 (2012).

The Court explained that a few things have to happen to establish prejudice under Strickland in this category of IAC: (1) you have to show a “reasonable probability” you and the prosecutor would have reached an agreement, (2) the court would’ve accepted it, and (3) your conviction or sentence would have been less severe under the plea deal than what you received after losing by going to trial.

That’s a lot to show but not impossible. When you request your case file from your previous lawyer, ask for any emails and notes between the lawyer and the prosecutor that were part of plea negotiations. United States v. Strother, 509 Fed. Appx. 571 (8th Cir. 2013) (email is considered a formal offer). Next, research your state’s laws and rules on the court accepting a guilty plea (Federal Rule of Criminal Procedure 11 for federal prisoners) and use it as a guide to meet the second prong. Finally, contrast the huge sentence you got for going to trial with the little one the prosecutor offered under the deal you rejected, and there’s your claim in a nutshell.

One thing to keep in mind is that it’s not about whether your decision to reject the plea offer was knowing and voluntary, as some courts have tried to say, and it has nothing to do with whether you got a fair trial after rejecting the plea offer. The Supreme Court in Lafler already rejected this line of reasoning and instructed that Strickland’s IAC standard is the proper measuring tool for these types of claims.


So, what if your lawyer failed to tell you about a good plea offer, and you ended up taking a worse offer later, or you pleaded guilty openly without an agreement and got a longer sentence?

In Missouri v. Frye, 566 U.S. 134 (2012), the Supreme Court addressed this issue. The State argued that because Frye had no constitutional right to a plea offer from the prosecutor there was no constitutional violation when his lawyer neglected to tell him about a favorable offer. But the Court wasn’t impressed. It explained that because guilty pleas are “so central” to the criminal justice system the Sixth Amendment right to counsel necessarily extends to “the plea-bargaining process.”

The Court therefore ruled that counsel has a “duty” to communicate all plea offers — even if he or she believes they were worthless. After all, the decision to plead guilty (or not) rests in your hands, not your lawyer’s.

The Court also clarified that whether the guilty plea Frye eventually did enter was knowing and voluntary was irrelevant. The focus of the inquiry, the Court said, is all about counsel’s actions in not advising him about the favorable plea offer. For you to establish prejudice for such a claim, you must show exactly the same three things as in Lafler (Lafler and Frye were decided the same day, and Lafler actually adopted Frye’s prejudice requirement).

In other cases where counsel has failed to advise of the option to plead guilty without a plea agreement — what’s called an open or “straight up” plea — courts have applied Frye to establish prejudice. Miller v. United States, 2015 U.S. Dist. LEXIS 1936 (M.D. Fla. 2015) (“the petitioner must show a reasonable probability that he would have actually taken advantage of that option” of the open plea, citing Frye).


State prisoners can take these claims to federal court after they’ve exhausted their state court post-conviction remedies. Under 28 U.S.C. § 2254(d)(1), a state prisoner may file a habeas corpus petition in federal court if the state court’s denial resulted in a decision that is contrary to or involved an unreasonable application of established federal law. Since every Supreme Court case listed in this column is considered “clearly established federal law,” the state court’s decision applying any of them can be challenged in federal court under § 2254. Rompilla v. Beard, 545 U.S. 374 (2005) (explaining when state courts misapply established federal law for habeas corpus relief).


Figuring out which category your IAC claim challenging your guilty plea falls under will greatly help you to focus your claim on the prejudice standard established by the Supreme Court for that category. And understanding the standard for your particular category will help you keep the court on track when the prosecutor tries to steer it off track in its response to your claims.

In my next column, we’ll examine the rules and laws on directly attacking a guilty plea. While many readers may be well beyond this point in their case, it will help you to understand what your lawyer should have done had he or she properly challenged your guilty plea at the appropriate time. This will help bolster your IAC claim challenging your guilty plea.

Editor’s note: This is the third column in a series on attacking the guilty plea.

This article originally appeared in the August, 2020 issue of Criminal Legal News. It is reprinted with permission.  Copyright, 2020 Criminal Legal News

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