by Dale Chappell

It’s long been said that a valid guilty plea goes a long way in barring post-conviction relief in the courts. While that can be true for challenges to the guilty plea itself, it’s often not true for challenges to a sentence resulting from that guilty plea. After navigating the procedural hurdles for these claims, federal habeas corpus relief has routinely been granted to petitioners challenging illegal sentences, even those with binding plea agreements.

Assuming you’re familiar with my numerous writings on how to file successful federal habeas claims, let’s take a closer look at this ‘guilty plea bar’ to federal habeas relief.

A Guilty Plea Doesn’t Automatically Bar Federal Habeas Relief

When it comes to challenging a sentence that’s been upended because of a subsequent court decision, a guilty plea can be an obstacle to habeas relief in federal court. The basis for this stems from Supreme Court decisions that have set out to legitimize guilty pleas when plea bargaining became an accepted form of resolving a criminal case.

For example, when a federal prisoner challenged his guilty plea after the Supreme Court later declared the death penalty unconstitutional for his offense, the Court said that his guilty plea to avoid facing death wasn’t rendered invalid simply because of the Court’s later decision: “A voluntary plea of guilty intelligently made in light of the then applicable law does not become vulnerable because later judicial decisions indicate that the plea rested on a faulty premise.” Brady v. United States, 397 U.S. 742 (1970).

Some courts have relied on Brady to reject habeas challenges to sentences invalidated by later Supreme Court decisions. See, e.g., Davila v. United States, 843 F.3d 729 (7th Cir. 2016). But most courts say that a collateral attack on a sentence is not the same as an attack on a conviction. See United States v. Rush, 910 F. Supp. 2d 286 (D.D.C. 2012) (“in the sentencing context, the petitioner’s burden of establishing prejudice is somewhat lighter” than with a re-trial).

In the wake of recent Supreme Court decisions invalidating the “residual clause” in several federal criminal statutes as unconstitutional, federal courts have granted relief in scores of post-conviction cases attacking the sentence, despite these sentences being the result of a knowing and voluntary guilty plea. See United States v. Sumner, 2022 U.S. Dist. LEXIS 58700 (D.D.C. 2022) (collecting cases). Over 25,000 habeas petitions were filed in the federal courts in 2016, and nearly half of them were based on just one of these Supreme Court decisions declaring the residual clause unconstitutional. With at least 95% of convictions obtained via a guilty plea, it’s clear that a guilty plea doesn’t bar federal habeas relief for an illegal sentence.

Even the Threat of an Illegal Sentence Opens the Door for Relief

What if someone pleads guilty and agrees to a lighter sentence in order to avoid a threatened harsher penalty if they don’t, and then that threatened punishment winds up being illegal or even non-existent?

In the Sumner case noted above, Sumner had agreed to a statutory maximum sentence of 25 years in order to avoid a mandatory life sentence in federal prison. He had at least two qualifying prior convictions and his federal bank robbery was a “third strike” under 18 U.S.C. § 3559(c), which required a life sentence in prison.

But his prior Pennsylvania robberies only qualified under the residual clause of § 3559. When the Supreme Court struck down the residual clause, this made Sumner’s agreed-upon sentence to avoid life in prison open to challenge. Citing numerous other cases that granted relief to petitioners who took plea deals due to threats of punishment later invalidated by the Supreme Court, the District Court granted relief and vacated Sumner’s 25-year sentence.

A Binding Plea Agreement Does Not Bar Habeas Relief

Sumner’s plea agreement was binding on the court under Federal Rule of Criminal Procedure 11(c)(1)(C), which meant that the court had to impose the 25-year sentence if it accepted the plea agreement. But the question was whether this binding agreement required Sumner to serve what would become an illegal sentence. The court said it didn’t since it was the product of a threat of an unconstitutional punishment. This was true even though the plea agreement stipulated that Sumner was also “designated” as a career offender, requiring a higher sentence.

In United States v. Wolf, 2017 U.S. Dist. LEXIS 25969 (M.D. Pa. 2017), the court addressed a similar dilemma: “We will not uphold Defendant’s now-unconstitutional sentence in light of his plea agreement, as doing so would result in a miscarriage of justice by sustaining what has proven to be an unlawful application of the [punishment].”

Besides the threat of an unconstitutional punishment that induced Sumner to take the 25-year deal, the court noted that his sentencing range without the mandatory career offender penalty (because it, too, was impacted by removal of the residual clause) was only 19 to 21 years. The fear of both the § 2559 life sentence and the career offender designation caused him to agree to the 25-year sentence, the court said, and his challenge was not barred by the binding plea agreement.

Procedural Bars to Habeas Relief Still Apply

Even if your sentence clearly becomes illegal because of a subsequent Supreme Court decision or applicable change in the law, courts say that the procedural default rule still applies. This rule, explained in Bousley v. United States, 523 U.S. 614 (1998) (“In this case, petitioner contested his sentence on appeal, but did not challenge the validity of his plea. In failing to do so, petitioner procedurally defaulted the claim he now presses on us.”), says that any claims for habeas relief that could’ve been raised on appeal but weren’t are barred from relief, unless you can show (1) cause for your failure to raise them earlier and prejudice if the error remains or (2) actual innocence of the offense.

Be aware of the “IAC trap” with habeas claims relying on new, retroactive Supreme Court decisions. While ineffective assistance of counsel (“IAC”) is the most common way to get around procedural default in a habeas case, see Massaro v. United States, 538 U.S. 500 (2003), counsel is not ineffective for failing to predict what the Supreme Court might do in a future case. See, e.g., Cooks v. United States, 2015 U.S. Dist. LEXIS 153968 (S.D. Ga. 2015).

Instead, the “novelty” exception would avoid procedural default with a new Supreme Court decision. See Reed v. Ross, 468 U.S. 1 (1984). This method requires a Supreme Court decision that (1) overrules a prior Supreme Court decision, (2) overrules a “longstanding and widespread practice” by the lower courts, or (3) disapproves of a practice the Supreme Court itself once supported. In other words, it creates a new path that no one could have reasonably predicted.

Showing novelty is only part of the process, though. You’ll also have to show prejudice or that there is a reasonable probability the result of the proceeding would have been different but for the error.

Going back to the Sumner case, novelty avoided procedural default to allow the claims to move forward. The court found that, until the Supreme Court’s retroactive decision declaring the residual clause unconstitutional, he “did not have a reasonable basis upon which to challenge the constitutionality of [the] residual clause.”

As for showing prejudice, the court found that the lower sentence Sumner would have faced without the residual clause qualifying his priors for the life sentence or the career offender penalty resulted in a reasonable probability of a different outcome.

Appeal Waivers Can Be Ignored to Challenge an Illegal Sentence

Every plea agreement involves some kind of waiver of the right to challenge the conviction and/or sentence, and courts routinely uphold these waivers if they’re knowing and voluntary (just like with a guilty plea). But any error that affects the validity of the plea agreement itself voids the waiver.

Some courts are rather liberal with whether an error affects a waiver. In United States v. Suttle, 2016 U.S. Dist. LEXIS 79964 (E.D. Wash. 2016), the court found that a challenge to a sentence after a subsequent Supreme Court decision declared the sentence unconstitutional was not barred by a waiver. “Defendant’s sentence is unconstitutional because the [erroneous sentence] affected every aspect of the proceedings beginning with the charging decision to the ultimate sentence pronounced by the court, and therefore, the waiver is not enforceable.”

But not every court takes such a broad view of an illegal sentence impacting “every aspect” of a case to void a waiver. In United States v. Barnes, 953 F.3d 383 (5th Cir. 2020), the conservative Fifth Circuit flatly refused to undo the post-conviction waiver in that case to allow a challenge to a sentence subsequently deemed illegal, saying the petitioner “assumed the risk that he would be denied the benefit of future legal developments.”

In conclusion, a guilty plea does not automatically bar habeas relief when an unforeseen error comes up later on. Sure, there are some procedural hurdles, as usual in federal habeas corpus, but they are not absolute roadblocks to relief.  

Dale Chappell has hundreds of published articles on federal habeas corpus and is the author of the Insider’s Guide series of post-conviction books. Follow his blog at www.zenlawguy.com and on Twitter: @zenlawguy.

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