Taking a Closer Look at Plea Waivers and Subsequent Challenges to Convictions and Sentences

Let’s talk about waivers for a moment. A recent case from the Second Circuit found that after the Supreme Court ruled certain provisions of some federal gun laws were unconstitutional, any relief could not be given because the defendant had agreed in a plea deal not to file an appeal or § 2255 motion. Like thousands of prisoners when Johnson and Davis were decided, the movant here filed a § 2255 motion attacking his now-unconstitutional sentence. The government invoked the waiver, and the district court dismissed the motion.

But doesn’t a waiver become invalid if the sentence is later declared illegal or unconstitutional? It all depends on the exact language of the waiver. Lots of prisoners got relief after the retroactive constitutional decisions in Johnson and Davis, despite having a waiver in their plea agreement. Why? Their waiver included language saying they could attack an illegal sentence, an exception most waivers have. The problem in Cook v. United States, 2023 U.S. App. LEXIS 27383 (2d Cir. Oct. 16, 2023), though, was that the waiver didn’t have that language. In fact, here’s exactly what it said:

The Defendant waives any and all rights, including those conferred by 18 U.S.C. § 3742 and/or 28 U.S.C. § 2255, to appeal or collaterally attack his conviction and any sentence of imprisonment of 240 months or less [and] agrees that should the sentence imposed on the Indictment and Information exceed 240 months, this would not permit him to withdraw his guilty pleas or to appeal or collaterally attack his convictions, but would merely allow the Defendant to appeal or collaterally attack the sentence(s) imposed by the Court, to the extent permitted by 18 U.S.C. § 3742 and/or 28 U.S.C. § 2255.

The movant in Cook was sentenced to 20 years in federal prison without parole for conspiracy to commit Hobbs Act robbery and use of a firearm in furtherance of that crime of violence (which resulted in death). While a conspiracy to commit a crime of violence is not a valid predicate anymore for the firearm conviction in this case, the limited exception in the waiver barred the § 2255 motion. The movant will have to serve his sentence because the government enforced the waiver, and because no exceptions applied.

An important point about waivers is that the language in a plea agreement must be construed narrowly, and any unclear language must be construed in favor of the defendant. That’s because plea agreements are contracts, and any unclear language goes against the benefiting party in the contract (usually the one who writes the contract).

So, if the waiver says someone cannot attack their conviction but says nothing about their sentence, the waiver only applies in a challenge to the conviction. If the waiver waives the right to appeal but says nothing about § 2255 or collateral attack, the waiver only applies if a direct appeal is filed.

An important question I’m getting lately is whether a collateral attack waiver bars compassionate release motions under 18 U.S.C. § 3582, asking for relief under compassionate release or due to a retroactive guideline amendment. At least one court has said that a waiver must expressly say § 3582 motions are waived. United States v. Goodloe, 388 F. App’x 500, 503 (6th Cir. 2010) (“because the waiver is at best ambiguous as to the § 3582 motion, we deny the government’s motion to dismiss”).

Most courts agree that certain exceptions should apply to waivers in plea agreements. For example, in United States v. Hahn, 359 F.3d 1315 (10th Cir. 2004), the court held that “waivers are subject to certain exceptions, including [1] where the district court relied on an impermissible factor such as race, [2] where ineffective assistance of counsel in connection with the negotiation of the waiver renders the waiver invalid, [3] where the sentence exceeds the statutory maximum, or [4] where the waiver is otherwise unlawful.”

In sum, it comes down to a few key points. First, the language of the waiver must undoubtedly bar the relief being sought. If not, it’s construed in favor of the defendant/movant. Second, the waiver must be valid, meaning that it’s not tainted by unconstitutional or illegal conduct by the government. Third, a waiver cannot create a “miscarriage of justice,” which is usually defined as an illegal sentence or conviction. Again, read Hahn for more on this.

In my book, Insider’s Guide: Federal Habeas Corpus for Federal Prisoners, I go into great detail on waivers. But for now, here’s a list of some resources to learn more about waivers:

United States v. Frazier-LeFear, 665 F. App’x 727 (10th Cir. 2016) (discussing Hahn’s “otherwise unlawful” waiver exception)

In re Brooks, No. 19-6189, 2020 U.S. App. LEXIS 6371 (6th Cir. Feb. 28, 2020) (sentence appeal waiver did not bar challenge to conviction)

Vowell v. United States, 938 F.3d 260 (6th Cir. 2019) (clarifying that a change in law can render a sentence in excess of statutory max and void the waiver)

Dale Chappell is an expert on federal postconviction relief and the author of hundreds of articles and several books on challenging illegal and wrongful convictions and sentences. He is a former staff writer for Criminal Legal News Magazine and the author of the blog zenlawguy.com.

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