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Attacking the Guilty Plea: Waivers, Breaches, and Getting More Time After a Successful Challenge

Waivers in Plea Agreements

Over 67 percent of plea agreements in 2015 had waivers, and these waivers are usually boilerplate language that the government uses in all of its agreements. Rarely are these waivers negotiated by defense counsel, and they’re so common that defendants often accept them as a necessary evil to pleading guilty.

But a defendant can’t just waive his rights without having notice of those rights. In United States v. Chua, 349 F. Supp. 3d 214 (E.D.N.Y. 2018), Judge Jack Weinstein criticized the government for using a “blanket” waiver barring a defendant’s right to challenge his guilty plea or sentence, without listing the rights he would be waiving. The judge “amended” the waiver to address each of the rights the defendant had that he would be waiving (or not waiving).

Any waiver in your plea agreement barring a challenge to your guilty plea is an “affirmative defense” that the government must invoke. Federal Rule of Civil Procedure 8(c)(1) lists affirmative defenses that a responding party must raise or else they’re forfeited. Because the civil rules apply to habeas corpus proceedings in federal court and because a habeas proceeding (including a 28 U.S.C. § 2255 proceeding) is a “civil proceeding,” the government is required to raise any waivers that are in your plea agreement for them to be effective.

While a court may not invoke the waiver itself, it can – and usually does – ask the government to indicate whether they’re going to invoke the waiver. See Burgess v. United States, 874 F.3d 1242 (11th Cir. 2017) (explaining this process and vacating a § 2255 denial where the district court invoked the collateral attack waiver).

When interpreting waivers in plea agreements, the court refers to contract law since plea agreements are “contracts.” Santobello v. New York, 404 U.S. 257 (1971). Under the principles of contract law, any ambiguities in the plea agreement (the contract) is construed against the drafter of the contract (the government).

Collateral Attack Waivers Versus Appeal Waivers

Because a plea agreement is construed strictly against the government, when a waiver says that you’re waiving your right to “appeal,” courts have held that this waiver doesn’t also apply to collateral attacks, which include challenges under 28 U.S.C. §§ 2254 (by state prisoners) and 2255 (by federal prisoners). See Hunter v. United States, 160 F.3d 1109 (6th Cir. 1998).

However, the same rules that apply to appeal waivers equally apply to collateral attack waivers. This means that any exceptions that would apply to appeal waivers also apply to collateral attack waivers. We go over some of common exceptions next.

Exception: Waiver Not Knowing and Voluntary

Not only must your guilty plea be “knowingly and voluntarily made,” but any waiver of your rights in a plea agreement must be knowing and voluntary. United States v. Ruiz, 536 U.S. 622 (2002). The Supreme Court in Ruiz stressed that this means you’re aware of “the relevant circumstances and likely consequences” of the waiver.

What would make a waiver not knowing and voluntary? Several things, but a few have generally been accepted as negating a waiver. For example, just as ineffective assistance of counsel (“IAC”) can render a guilty plea not knowing and voluntary, IAC in negotiating a plea agreement can render a waiver (as well as the agreement itself) invalid. Hurlow v. United States, 726 F.3d 958 (7th Cir. 2013); Padilla v. Kentucky, 559 U.S. 356 (2010) (the negotiation of a plea agreement is a “critical stage” of a criminal proceeding requiring effective assistance of counsel).

A more controversial issue that makes a waiver not knowing and voluntary is when the prosecution withholds favorable evidence from a defendant. In Chua, Judge Weinstein acknowledged that the Second Circuit had not yet addressed whether such an egregious act by the government could invalidate a collateral attack or appeal waiver. But citing the prevalence of guilty pleas in the criminal justice system, he concluded that when the government withholds evidence, the right to attack a conviction is not waived. “This right is retained as part of the ‘voluntary and knowing’ exception,” he said. Be aware that not all the courts are on the same page here, and the Supreme Court hasn’t yet addressed the issue. See Friedman v. Rehal, 618 F.3d 142 (2d Cir. 2010) (discussing this point).

Lack of notice of the nature of the charges also would render a guilty plea waiver not knowing and voluntary. Frederick v. Warden, 308 F.3d 192 (2d Cir. 2002) (a defendant must have “real notice of the true nature of the charge” for a waiver to be valid).

Exception: A Change in the Law

When the law changes and invalidates a conviction (or sentence), some courts have held that a waiver doesn’t bar a challenge based on that new law. This includes major court decisions applying retroactively, as well as changes in the law by lawmakers. For example, when the Supreme Court retroactively invalidated the residual clause of the Armed Career Criminal Act in Johnson v. United States, 135 S. Ct. 2551 (2015), some courts held that a collateral attack waiver doesn’t bar a challenge to the now unconstitutional sentence. E.g., United States v. Cornette, 932 F.3d 204 (4th Cir. 2019). The reasoning there was that the district court never had authority to impose the sentence because it’s an illegal sentence. But not all courts agree. In United States v. Barnes, 953 F.3d 385 (5th Cir. 2020), the court cited Cornette but disagreed with its ruling, upholding a waiver in the face of an unconstitutional sentence. This same reasoning could apply to waivers of guilty plea challenges.

However, the same court that allowed the challenge in Cornette, despite a waiver, recognized that not all changes in law nullify a waiver. “A plea agreement, like any contract, allocates risk. And the probability of a favorable change in law occurring after a plea is one of the normal risks that accompanies a guilty plea,” the court said in United States v. Archie, 771 F.3d 217 (4th Cir. 2014). But this “risk” goes both ways. When the government tried to reinstate charges it tossed under a plea agreement after a defendant later successfully challenged his conviction due to a retroactive change in the law by the Supreme Court, a district court refused to allow this, citing Archie’s “risk” with plea agreements. Diri v. United States, 2019 U.S. Dist. LEXIS 175043 (W.D.N.C. 2019).

Exception: Impermissible Factors

The Supreme Court has recognized several instances where a waiver couldn’t bar a challenge when a conviction (or sentence) is based on “constitutionally impermissible factors.” E.g., Menna v. New York, 423 U.S. 61 (1975) (guilty plea did not bar challenge under Double Jeopardy Clause); Blackledge v. Perry, 417 U.S. 21 (1974) (guilty plea did not bar prosecutorial vindictiveness challenge). And every court has held that race may not play a factor in a conviction or sentence, despite any waivers. See United States v. Marin, 961 F.2d 493 (4th Cir. 1992).

Exception: Miscarriage of Justice

A waiver may not bar a challenge to a “miscarriage of justice,” such as actual innocence. In United States v. Viera, 674 F.3d 1214 (10th Cir. 2012), the court established four situations that would amount to a miscarriage of justice to invalidate a waiver: (1) when the district court relied on an impermissible factor (noted above), (2) IAC in negotiating the plea agreement with the waiver, (3) an illegal sentence, or (4) “where the waiver is otherwise unlawful.” Unsurprisingly, actual innocence was also found to be a miscarriage of justice to avoid a waiver. McCann v. Mangialardi, 357 F.3d 782 (7th Cir. 2003).

Breach of a Plea Agreement Voids a Waiver

If the government breaches your plea agreement, any waiver you had in it barring a challenge goes out the door. In Santobello, the Supreme Court found that the government’s breach of a plea agreement allowed a defendant to seek a remedy despite the waiver. The Court suggested that the trial court could require “specific performance” of the agreement, or it could allow withdrawal of the guilty plea. This is where contract law comes into play. Specific performance is simply giving the aggrieved party the benefit it was supposed to get in the agreement, by the court enforcing the agreement.

The court made an important ruling in Santobello, holding that the government’s breach of the plea agreement is a due process violation. It’s important because while there’s no constitutional right to a plea agreement, when one is accepted by a defendant he’s afforded constitutional protections thereafter. Habeas corpus challenges are all about constitutional violations.

If you breach the plea agreement, the government then has the right to withdraw the agreement or to request specific performance, the same options you have. If the plea agreement is withdrawn, you’ll be starting over as if you’d never pleaded guilty. See Ricketts v. Adamson, 483 U.S. 1 (1987) (upholding death sentence after plea agreement with reduced charges vacated and reconviction on more serious charges when defendant breached agreement by refusing to testify).

A successful withdrawal of your guilty plea, however, is not a breach of your plea agreement. United States v. Newbert, 504 F.3d 1080 (1st Cir. 2007) (upholding district court’s ruling that withdrawal of guilty plea was not breach of plea agreement).

Getting More Time After a Successful Guilty Plea Challenge

Can you end up with more time if you successfully challenge (withdraw) your guilty plea? The short answer is yes. But not always. In North Carolina v. Pearce, 395 U.S. 711 (1969), the Supreme Court ruled that a longer sentence as a “penalty” for a successful challenge to a conviction is unconstitutional. But Pearce was about a higher sentence after a successful appeal and retrial, not a challenge to a guilty plea.

The Court later distinguished its holding in Pearce when a defendant successfully challenged his guilty plea but then lost at trial and got a longer sentence. In Alabama v. Smith, 490 U.S. 794 (1989), the defendant was originally sentenced to 30 years after a guilty plea. But then, he overturned that conviction on appeal and went to trial. When he lost, he got life plus 150 years. The judge said he was “too lenient” the first time.

Was this vindictive? Perhaps. But the Supreme Court upheld the harsh sentence, reasoning that evidence not normally brought to light during a guilty plea that comes out at trial can play a big part in a judge’s sentencing decision.

In United States v. Rodriguez, 602 F.3d 346 (5th Cir. 2010), it was the jury that handed out a harsher sentence and not the judge who originally sentenced the defendant upon reconviction after a guilty plea was successfully challenged. The new sentence was upheld by the court, saying that the jury didn’t know about the original sentence and therefore didn’t have a “personal stake” in it.

These cases suggest that when a sentence after a successful guilty plea is based on new facts or is imposed by someone having nothing to do with the original sentence, a harsher sentence is constitutionally permissible.


Plea agreements almost always contain waivers. But these waivers are not always obstacles to challenging a guilty plea. There are exceptions. Understanding the scope of the waiver and how it relates to your challenge will help guide you around that obstacle. 


Editor’s note: This is the fifth column in a 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. 


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