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

Establishing “prejudice” to undo a guilty plea because of the ineffective assistance of counsel (IAC) varies depending on which stage of the criminal case you`re in when you challenge your guilty plea. There are three main categories of IAC in the guilty plea context:

  1. Bad advice to plead guilt;
  2. Bad advice to reject a plea offer; and
  3. The failure of counsel to communicate a plea offer or option to plead guilty.

Under each category the IAC standard under Strickland v. Washington, 466 U.S. 668 (1984), applies, but how you establish prejudice under that standard varies by category.

Category 1: Bad Advice to Plead Guilty

By far, most claims attacking the guilty plea will fall under the first category, where counsel`s bad advice induced the guilty plea. Showing prejudice for this category was announced by the 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 the defendant in Hill hadn`t shown a reasonable probability of a different outcome because he never alleged he would have gone to trial had he received correct advice from counsel about his parole eligibility date before pleading guilty.

Whether you need to show that you would have won at trial to show prejudice under Hill is another matter and the federal courts couldn`t agree on this. In Lee v. United States, 137 S. Ct. 1958 (2017), the High 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 the defendant being deported as in the Lee case.

The Third Circuit, in Velazquez v. Sup`t Fayette SCI, 937 F.3d 151 (3d Cir. 2019), called Lee an “expansion” of the Hill standard for showing prejudice in challenging a guilty plea:

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.

The lesson is that chances of success at trial matter little if it`s the only rational option available to a defendant. Success at trial is just one of several factors considered in determining whether someone would have not pled guilty but instead would have insisted on going to trial — the prejudice standard under Hill.

What about other options, instead of going to trial? What if you could have negotiated a better plea deal or pled guilty without the plea deal you did take to preserve your rights, such as the right to appeal? 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”).

Besides counsel`s bad advice, the government`s misconduct could also provide grounds to establish prejudice under Hill. In Ferrara v. United States, 456 F.3d 278 (1st Cir. 2006), the court affirmed the grant of post-conviction relief undoing a guilty plea because the government`s prosecutors withheld “stunning” evidence that would have been favorable to the defense. “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,” the court said.

Category 2: Bad Advice to Reject a Plea Offer

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

The Court explained that a few things were required to show prejudice under this category of IAC in the guilty plea context:

  • You must show a “reasonable probability” that you and the prosecutor would have reached an agreement;
  • The court would have accepted that agreement; and
  • That 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 old lawyer, make sure you ask for any emails and notes between your lawyer and the prosecutor that were part of the plea negotiations. Note that an offer by email is considered a “formal” plea offer. United States v. Strother, 509 Fed. Appx. 571 (8th Cir. 2013).

Next, research your state`s laws and rules on the court accepting a guilty plea and use it as a guide to meet the second prong. That would be Federal Rule of Criminal Procedure 11 for federal prisoners, and most states use a rule similar to Rule 11.

Finally, contrast the huge sentence you got for going to trial with the little sentence you would have received had you pled guilty under the plea offer.

Category 3: The Failure of Counsel to Communicate a Plea Offer or Option to Plead Guilty

What if your lawyer failed to even tell you about a good plea offer and you ended up taking a worse offer or pled guilty without an agreement, and got a longer sentence? In Missouri v. Frye, 566 U.S. 134 (2012), the Supreme Court addressed this issue.

In that case, the state had argued that because the defendant had no constitutional right to a plea offer from the prosecutor there was no constitutional violation when his lawyer neglected to tell him about the offer. The Court strongly disagreed, explaining that guilty pleas are “so central” to the criminal justice system that the Sixth Amendment right to counsel necessarily extends to the “plea bargaining process.”

Counsel has a “duty” to communicate all plea offers, even if he believes they are worthless, the Court said in Frye. After all, the decision to plead guilty is not up to counsel, but up to the defendant. That`s been settled law for decades.

The way to show prejudice for this third category in challenging a guilty plea is the same as that above, under Lafler, noted above. Both cases were decided the same day by the Supreme Court and Frye actually adopted Lafler`s prejudice standard.

In the case where counsel fails to advise a defendant that he has the option to plead without a plea agreement, or what`s called an “open plea,” courts have applied the prejudice standard announced in Frye. In Miller v. United States, 2015 U.S. Dist. LEXIS 1936 (M.D. Fla. 2015), the court cited Frye and concluded that in order to show prejudice, “the petitioner must show a reasonable probability that he would have actually taken advantage of that option” to plead openly.

In conclusion, figuring out which category your IAC claim challenging your guilty plea falls under will focus your claim on the proper prejudice standard established by the Supreme Court for that category of claims. That`s the first step in crafting a successful challenge to your guilty plea.


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