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Attacking the Guilty Plea: The Ineffective Assistance of Counsel Standard

More than 95 percent of state and federal prisoners plead guilty, and most of them do so on the advice of their lawyer. A successful attack on a guilty plea would then depend on showing that counsel’s bad advice to plead guilty rendered the plea not “knowing and voluntary.”

We covered the knowing and voluntary nature of a guilty plea in my last column in this series on attacking the guilty plea (see March 2020 CLN, p.18). In this column, we will go over the ineffective assistance of counsel (“IAC”) standard in the guilty plea context.


A.  The Negotiation of a Guilty Plea of a ‘Critical Phase’ of a Criminal Case

Criminal defendants are expected to rely on their lawyer’s advice in deciding to plead guilty. And the U.S. Supreme Court has recognized as much. In Padilla v. Kentucky, 559 U.S. 356 (2010), the Court reaffirmed its longstanding position on the issue and held that “the negotiation of a plea bargain is a critical phase of litigation for purposes of the Sixth Amendment right to effective assistance of counsel.”

The Court’s statement was hardly a surprise. For over 70 years, the Court has said lawyers are required to give clients their “informed opinion as to what plea should be entered.” Von Moltke v. Gillies, 332 U.S. 708 (1948). The Court further said that an “intelligent assessment” of the advantages to pleading guilty is “impossible” without counsel’s advice. Brady v. United States, 397 U.S. 742 (1970).

These are just a sampling of the Supreme Court cases that have all said the same thing over and over: counsel’s advice on whether to plead guilty is very important. The decision to take or reject a plea, go to trial, plead without a plea agreement, or any combination of these rests so much on counsel’s advice that bad advice can render a guilty plea involuntary.


B.  IAC Implicates the Voluntariness of a Guilty Plea

“A guilty plea can be involuntary as a result of the ineffective assistance of counsel,” says the U.S. Court of Appeals for the Sixth Circuit. United States v. Gardner, 417 F.3d 541 (2005). Have you ever wondered why this is true? Sure, bad advice to plead guilty can be “prejudicial” because the outcome of your case could have been significantly different (better) had a different choice been made. But, that’s only part of why IAC makes a guilty plea involuntary.

Your decision to plead guilty stems from the information and advice you received from your lawyer. The amount of prison time you faced, any fallout from the conviction (e.g., deportation), and any rights you waived by pleading guilty are all affected by the decision to plead guilty. All of this formed your understanding of the guilty plea — or the “knowing and voluntary” nature of the plea. Bad advice to plead guilty, then, taints the voluntariness of your plea because it affects your understanding of your plea. United States v. Keller, 902 F.3d 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 reasoning was the basis of the Supreme Court’s decision in Tollett v. Henderson, 411 U.S. 258 (1973). In that case, the Supreme 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 set forth in [the Court’s decision on effective assistance of counsel].” The Tollett Court recognized that other constitutional violations may “play a part” in determining the voluntariness of a guilty plea, but “they are not themselves independent grounds for federal collateral relief.” Instead, it’s all about the advice of counsel to plead guilty.

Let’s take a look at how counsel’s advice could make a guilty plea not “knowing and voluntary.” In the child sexual exploitation case against Subway’s ex-pitchman Jared Fogle, the former head of Fogle’s charitable foundation, Russell Taylor was charged with multiple counts of producing child pornography, in violation of 18 U.S.C. § 2251, depicting “sexually explicit conduct.” Immediately, Taylor’s lawyer advised him to plead guilty because he faced such a high sentence if he lost at trial. Taylor pleaded guilty to the charges upon his lawyer’s advice and received a 27-year sentence.

When Taylor later challenged in a motion under 28 U.S.C. § 2255 that his guilty plea was not knowing and voluntary, claiming that his lawyer never advised him that his conduct did not amount to the crimes charged, the court agreed and vacated his conviction and sentence.

The court found that Taylor’s lawyer had not only failed to advise him that he didn’t break the law he was charged with, but also that he failed to object to the presentence report’s “inaccurate description” of the offense conduct. Additionally, he failed to advise the court that Taylor’s conduct didn’t meet the elements of the charged offenses. He even stipulated in the plea agreement with the government that Taylor’s conduct met the elements of the charges.

The court tossed his guilty plea based on the shockingly bad advice by counsel to plead guilty, despite the fact that Taylor stood before the court, under oath, and pleaded guilty to the charges, saying that he had understood the charges. His understanding, though, was poisoned by his counsel’s ineffective assistance, and his plea was therefore not knowing and voluntary, the court concluded. Taylor v. United States, 2020 U.S. Dist. LEXIS 34341 (S.D. Ind. 2020).

Not only can counsel’s bad advice kill a guilty plea but so can counsel’s bad acts that led up to the plea. In Missouri v. Frye, 566 U.S. 134 (2012), the Court noted a distinction from its earlier cases that it wasn’t counsel’s advice that led to an invalid plea but “the course of the legal representation that proceeded it.” The Court held that counsel’s failure to advise of a more favorable plea offer made the defendant’s guilty plea under a harsher agreement not fully informed and therefore invalid.

IAC in any form undermines the knowing and voluntary nature of a guilty.


C.  Strickland v. Washington in the Guilty Plea Context

“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). But how do you measure whether counsel was “competent”? The year prior to Hill, the Court had established in Strickland v. Washington, 466 U.S. 668 (1984), a two-part test in assessing whether counsel’s performance meets the Sixth Amendment guarantee to the right to counsel in criminal cases. In Hill, the Court extended the Strickland test to IAC claims in the guilty plea context (Strickland was about counsel’s performance during trial).

The familiar Strickland standard requires a showing (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 prong, known as the “prejudice” prong, is crucial because without showing prejudice counsel is not constitutionally ineffective.

The Supreme Court has recognized three different “prejudices” in the guilty plea context: (1) accepting a guilty plea that wouldn’t have been accepted absent IAC, (2) rejecting a favorable plea offer because of IAC, and (3) IAC that led to the failure to communicate a plea offer or option. We go over these in detail in subsequent columns on attacking the guilty plea, so we won’t spend much time on these here. But the whole idea under each prejudice showing is that the guilty plea would have been different without the IAC.

In establishing prejudice after a guilty plea, courts apply the Strickland principles. A “reasonable probability” under Strickland simply means to “undermine confidence in the outcome,” the Court said. This reasonable probability bar is significantly lower than the “beyond reasonable doubt” standard and is even lower than the “more likely than not” standard. As one circuit court of appeals noted, “Strickland asks if a different result is ‘reasonably probable,’ not if it is possible.” Brown v. United States, 729 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 embraced the idea that counsel’s strategic decisions are insulated from being attacked as IAC. But this doesn’t mean anything if counsel didn’t do her homework. The failure to investigate and research the case and the law is not a “strategy” by anyone’s definition. Taylor (“because [counsel] never considered an alternative to a [guilty] plea, his pursuit of a [guilty] plea was not a reasonable strategic decision”).


D.  Relief is Available for State Prisoners in Federal Court

After exhausting their state court remedies, state prisoners attacking their guilty pleas can take their challenges to federal court if denied by the state courts. 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 was contrary to, or involved an unreasonable application of, clearly established federal law, as determined by the Supreme Court.”

Since Strickland is “clearly established federal law,” a state court decision that’s contrary to or is an unreasonable application of the Supreme Court’s holding would be open to further attack 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’s not enough for the state court to apply Strickland incorrectly. You must show that the state court applied Strickland in your case “in an objectively unreasonable manner.” Rompilla v. Beard, 545 U.S. 374 (2005). In other words, the state court’s decision must not only be wrong, you must show that any reasonable judge would not have made the same mistake. That’s the “objectively unreasonable” measuring stick.

Since we’re dealing with IAC and guilty pleas, the actual standard that the state court must apply is the one that the Supreme Court announced in Hill, which applied Strickland to the guilty plea context. You must show that the court violated the Hill standard, not just Strickland. Your research will likely have better results if you include cases that have applied Strickland under the Hill decision, even though Hill was largely about finding Strickland prejudice in the face of a guilty plea.


IAC can clearly lead to a guilty plea that is constitutionally invalid and open to collateral attack. Becoming familiar with Strickland will help in identifying whether your lawyer’s errors were grave enough to render your guilty plea not knowing and voluntary. In the next column in this series, we will begin our journey into the various ways the Supreme Court has recognized Strickland prejudice in attacking the decision to plead guilty, starting with the Hill prejudice standard.  

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

About the author: Dale Chappell is a staff writer for Criminal Legal News and Prison Legal News. For over a decade, he has helped prisoners challenge their wrongful convictions and sentences, with dozens being released from prison. He is a member of the National Lawyers Guild and was a 20-year career firefighter before becoming an advocate for prisoners. He is the author of two books written in conjunction with attorney Brandon Sample: WinningCites: Section 2255, A Handbook for Prisoners and Lawyers and WinningCites: Attacking the Guilty Plea. Email for more information on these books (prisoner emails accepted).

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