How to Prove Your Lawyer's Mistakes Hurt You in a Guilty Plea Case

To win a claim that your lawyer's mistakes tainted a guilty plea, you must show "prejudice," meaning the mistakes actually hurt you. What that takes depends on what went wrong. The last column covered the general test for ineffective assistance of counsel (IAC) in guilty plea cases under Strickland v. Washington, 466 U.S. 668 (1984). This column covers the prejudice part.

There are three main kinds of IAC in plea cases:

1. Bad advice to plead guilty.
2. Bad advice to reject a plea offer.
3. Failing to tell you about a plea offer or an option to plead.

Strickland applies to all three, but what you must show to prove prejudice is different for each. The sections below take them one at a time.

Bad Advice to Plead Guilty

Most plea-related IAC claims are in this group. The Supreme Court set the prejudice test 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 to a guilty plea. Hill lost because he never claimed he would have gone to trial if his lawyer had correctly advised him about parole eligibility.

Do you have to show you would have won at trial? Not necessarily. In Lee v. United States, 137 S. Ct. 1958 (2017), the Court recognized that sometimes throwing a "Hail Mary" by going to trial is more rational than a plea with a certain bad result, like deportation. Lee took another look at proving prejudice when bad legal advice led to a guilty plea.

Lee's guilty plea all but guaranteed he would be deported, while going to trial gave him a slim chance of acquittal. The government argued he would surely have lost at trial. The Court answered: "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." Since deportation was almost as certain either way, a small chance at trial made going to trial a rational choice.

The Third Circuit described the Hill prejudice test as "expanded" by Lee and several other Supreme Court cases. It summed it up: "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).

In other words, your chances at trial matter little if trial was the only rational option. They are just one of several factors in deciding whether you would have "insisted on going to trial."

Do you have to show you would have gone to trial, rather than gotten a better deal? Some courts accept other alternatives. See, e.g., United States v. Swaby, 855 F.3d 233 (4th Cir. 2017) ("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).

Government misconduct can also support prejudice under Hill. In one case, prosecutors deliberately withheld "stunning" evidence that helped the defense. The court found 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).

Bad Advice to Reject a Plea Offer

What if your lawyer told you to turn down a good offer because you would surely win at trial, and you lost? The Supreme Court addressed this in Lafler v. Cooper, 566 U.S. 156 (2012).

To show prejudice, you must show a reasonable probability that:

1. You would have accepted the offer, and the prosecutor would not have withdrawn it;
2. The court would have accepted the deal; and
3. Your conviction or sentence under the deal would have been less severe than what you got after trial.

That is a lot to prove, but it can be done. When you ask your former lawyer for your case file, request any emails and notes about plea talks with the prosecutor. United States v. Strother, 509 Fed. Appx. 571 (8th Cir. 2013) (treating an email as a formal offer). Then look at the rules on when a court accepts a plea (Federal Rule of Criminal Procedure 11 in federal cases) for the second point. Finally, compare the long sentence you got after trial with the shorter one offered in the deal you rejected. That is your claim in a nutshell.

The question is not whether your decision to reject the offer was knowing and voluntary, as some courts have tried to say, and it is not whether your trial was fair. Lafler rejected those approaches and held that Strickland is the right test.

Failing to Tell You About an Offer

What if your lawyer never told you about a good offer, and you later took a worse deal or pleaded guilty without one?

The Supreme Court addressed this in Missouri v. Frye, 566 U.S. 134 (2012). The State argued there was no violation because Frye had no constitutional right to a plea offer. The Court disagreed. Because guilty pleas are "so central" to the justice system, the right to counsel covers "the plea-bargaining process."

The Court held that a lawyer has a duty to tell you about formal plea offers from the prosecution. The decision to plead guilty is yours, not your lawyer's.

The Court also said it did not matter whether Frye's later guilty plea was knowing and voluntary. The focus is the lawyer's failure to tell him about the offer. To show prejudice, you must show essentially the same things as in Lafler. (The two cases were decided the same day, and Lafler used a prejudice test that tracks Frye's.)

Some courts have applied Frye when a lawyer failed to tell a client about the option of an "open" plea, meaning pleading guilty without a plea agreement. 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," citing Frye).

Federal Relief for State Prisoners

State prisoners can bring these claims in federal court after using up their state court options. Under 28 U.S.C. § 2254(d)(1), relief is possible if the state court's decision was contrary to, or an unreasonable application of, clearly established federal law. Every Supreme Court case in this column counts as clearly established federal law. Rompilla v. Beard, 545 U.S. 374 (2005) (explaining when a state court's misapplication of federal law allows habeas relief).

Conclusion

Figure out which kind of IAC claim you have, then focus on the prejudice test the Supreme Court set for that kind. Knowing the right test helps you keep the court on track when the prosecutor tries to steer it elsewhere.

The next column looks at the rules for directly attacking a guilty plea. Even if your case is past that point, it can show what your lawyer should have done, which can strengthen your IAC claim.

Keep the filing deadline in mind. A federal prisoner's § 2255 motion generally must be filed within one year, usually counted from the date the conviction became final. 28 U.S.C. § 2255(f). State prisoners face a similar one-year limit for federal habeas petitions. 28 U.S.C. § 2244(d).

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

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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