Can Bad Advice From Your Lawyer Undo a Guilty Plea?

Bad advice from your lawyer can undo a guilty plea. If the advice fell below basic professional standards and it shaped your decision to plead, the plea may not have been "knowing and voluntary," and a court can throw it out. Because more than 95 percent of state and federal prisoners plead guilty, most on their lawyer's advice, this is usually the main route for attacking a plea.

The last column in this series covered what "knowing and voluntary" means. This column covers the standard for ineffective assistance of counsel (IAC), meaning a lawyer's work that falls below what the Constitution requires, when you plead guilty.

Plea Negotiations Are a "Critical Phase" of a Criminal Case

You are expected to rely on your lawyer's advice when deciding whether to plead guilty. The Supreme Court agrees. In Padilla v. Kentucky, 559 U.S. 356 (2010), it said "the negotiation of a plea bargain is a critical phase of litigation for purposes of the Sixth Amendment right to effective assistance of counsel."

That was not new. For over 70 years, the Court has said lawyers must give clients their "informed opinion as to what plea should be entered." Von Moltke v. Gillies, 332 U.S. 708 (1948). The Court has also said an "intelligent assessment" of whether to plead guilty is "impossible" without a lawyer's advice. Brady v. United States, 397 U.S. 742 (1970).

The message is the same in case after case: your lawyer's advice on whether to plead guilty matters a great deal. Your choice to take or reject a deal, go to trial, or plead without a deal depends so much on that advice that bad advice can make the plea involuntary.

Bad Advice Can Make a Plea Involuntary

"A guilty plea can be involuntary as a result of the ineffective assistance of counsel," the Sixth Circuit has said. United States v. Gardner, 417 F.3d 541 (6th Cir. 2005).

Why? Bad advice to plead guilty can be "prejudicial" because your case might have turned out much better with a different choice, but that is only part of the reason. Your decision to plead guilty rests on what your lawyer told you: how much prison time you faced, side effects like deportation, and what rights you were giving up. That is your understanding of the plea. Bad advice taints that understanding, and so taints the plea. United States v. Keller, 902 F.2d 1391 (9th Cir. 1990) ("A claim of ineffective assistance may be used to attack the voluntariness and hence the validity of a guilty plea").

This is the reasoning behind Tollett v. Henderson, 411 U.S. 258 (1973). There, the Court held that a defendant who pleads guilty "may only attack the voluntary and intelligent character of the guilty plea by showing that the advice he received from counsel was not within the standards" the Court had set. Other constitutional violations may "play a part," but "they are not themselves independent grounds for federal collateral relief." It is all about the lawyer's advice.

Here is an example. Russell Taylor, the former head of ex-Subway pitchman Jared Fogle's charity, was charged with producing child pornography under 18 U.S.C. § 2251, which requires images of "sexually explicit conduct." His lawyer quickly advised him to plead guilty because he faced so much time if he lost at trial. Taylor pleaded guilty and received a 27-year sentence.

Taylor later filed a motion under 28 U.S.C. § 2255 (a request asking the sentencing court to throw out a federal conviction or sentence). He argued his plea was not knowing and voluntary because his lawyer never told him some of the conduct did not meet the legal definition of the crimes charged. The court agreed and vacated his conviction and sentence.

The court found his lawyer failed to tell him that three of the charged counts were not supported. The lawyer also failed to object to the presentence report's "inaccurate description" of the conduct (the presentence report, or PSR, is the probation office's report the judge relies on at sentencing). He never told the court that the conduct did not meet the elements of those charges, and he even stipulated in the plea deal that it did.

The court threw out the plea because of the lawyer's shockingly bad advice, even though Taylor had stood before the court, under oath, pleaded guilty, and said he understood the charges. His understanding had been poisoned by his lawyer's bad advice, so his plea was not knowing and voluntary. Taylor v. United States, 2020 U.S. Dist. LEXIS 34341 (S.D. Ind. 2020).

Bad advice is not the only problem. A lawyer's failures leading up to the plea can matter too. In Missouri v. Frye, 566 U.S. 134 (2012), the Court noted that the question there was not the advice to plead guilty but "the course of legal representation that preceded it." The lawyer never told his client about a formal plea offer, which then expired. The client later pleaded guilty on worse terms. The Court held a lawyer generally must communicate formal plea offers, and failing to do so was deficient performance. It sent the case back to decide whether the client was harmed.

IAC in any form can undermine the knowing and voluntary nature of a guilty plea.

The Strickland Test for Guilty Pleas

"Defendants facing felony charges are entitled to the effective assistance of competent counsel," the Supreme Court said in Hill v. Lockhart, 474 U.S. 52 (1985). How do you measure that? A year earlier, Strickland v. Washington, 466 U.S. 668 (1984), set a two-part test for lawyers at trial. Hill applied that test to guilty pleas.

Under Strickland, you must show (1) "that counsel's representation fell below an objective standard of reasonableness" and (2) "that there is a reasonable probability that, but for counsel's unprofessional errors, the result of the proceeding would have been different." The second part is called "prejudice." Without it, there is no IAC claim.

The Supreme Court has recognized three kinds of prejudice in the plea context: (1) taking a plea you would not have taken without the bad advice, (2) rejecting a good plea offer because of bad advice, and (3) never learning of a plea offer or option. Later columns cover each one. The common idea is that the plea outcome would have been different without the IAC.

A "reasonable probability" is one that is enough to "undermine confidence in the outcome." That is lower than "beyond a reasonable doubt" and even lower than "more likely than not." Still, as one court put it, "Strickland asks if a different result is 'reasonably probable,' not if it is possible." Brown v. United States, 720 F.3d 1316 (11th Cir. 2013); see also United States v. Carthorne, 878 F.3d 458 (4th Cir. 2017) ("even when a district court has not committed plain error, counsel can have rendered ineffective assistance when counsel's errors were the result of a misunderstanding of the law").

Strickland protects a lawyer's strategic decisions from IAC claims, but that protection means little if the lawyer did not do the homework. Failing to investigate the case or research the law is not a "strategy." Taylor ("because [counsel] never considered an alternative to a [guilty] plea, his pursuit of a [guilty] plea was not a reasonable strategic decision").

Federal Relief for State Prisoners

After using up state court options, a state prisoner can bring a guilty plea challenge to federal court. Under 28 U.S.C. § 2254(d)(1), federal relief is possible if the state court's decision "was contrary to, or involved an unreasonable application of, clearly established Federal law, as determined by the Supreme Court."

Strickland is clearly established federal law. So a state decision that is contrary to it, or applies it unreasonably, can be challenged in federal court. Lafler v. Cooper, 566 U.S. 156 (2012) ("the state court's adjudication was contrary to clearly established federal law. And in that circumstance the federal courts in this habeas action can determine the principles necessary to grant relief.").

But it is not enough that the state court got Strickland wrong. You must show it applied Strickland "in an objectively unreasonable manner." Rompilla v. Beard, 545 U.S. 374 (2005). That means the decision was not just wrong, but unreasonably wrong: a mistake that fair-minded judges would not make. That is the "objectively unreasonable" measuring stick.

For guilty pleas, the standard the state court must apply is the one in Hill, which applied Strickland to guilty pleas. You must show the state court violated the Hill standard, not just Strickland. Your research will go better if you include cases applying Strickland through Hill, even though Hill was mostly about proving Strickland prejudice after a guilty plea.

Conclusion

IAC can make a guilty plea constitutionally invalid and open to collateral attack. Knowing the Strickland test will help you judge whether your lawyer's mistakes were serious enough. The next column begins a look at the ways the Supreme Court has recognized Strickland prejudice in challenges to a guilty plea, starting with the Hill prejudice standard.

For a federal prisoner, the usual tool is a § 2255 motion, and timing matters: it generally must be filed within one year, usually counted from the date the conviction became final. 28 U.S.C. § 2255(f). Before talking with a lawyer, gather the plea agreement, the plea and sentencing transcripts, the PSR if you have access to it, the judgment, and any letters or emails from your trial lawyer about the deal.

Editor's note: This is the second column in an ongoing series on attacking the guilty plea.

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

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