Jurisprudence

Why All Nine Justices Overturned a Ludicrously Cruel Prison Sentence

Wooden v. United States shows the Supreme Court at its best—and throws its usual dysfunction into sharp relief.

Three justices in their robes stand in the House chamber
Justice Stephen Breyer, Chief Justice John Roberts, and Justice Elena Kagan. Win McNamee/Getty Images

Wooden v. United States is almost enough to restore one’s faith in the Supreme Court’s ability to act like a real court. In the opinion, which the court handed down Monday morning, all nine justices ruled in favor of a criminal defendant without a whiff of partisanship or motivated reasoning. They rejected a harsh and ludicrous interpretation of federal statute that would have transformed short prison terms into potential lifetime sentences. And they engaged in an important, cross-ideological debate about draconian yet ambiguous penal laws.

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By Monday afternoon, politics had already crept back into the court’s decision-making. And that troublesome trend is likely to continue through the end of the term. But for a brief moment on Monday, the court provided a glimpse of what the institution might look like if all nine justices acted like real judges and not junior varsity politicians.

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Wooden is a cautionary tale about the dangers that arise when overzealous prosecutors get their hands on an underbaked statute. The case’s roots go back to 1997, when William Dale Wooden broke into a Georgia storage facility with three friends. After burgling the first unit, they broke through the drywall into the second unit, then the third, working their way across 10 units. This incident was not exactly an Ocean’s Eleven–caliber heist, and law enforcement quickly caught the perpetrators. Wooden pleaded guilty to 10 counts of burglary, receiving an eight-year prison sentence.

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This crime would have disappeared from memory had a police officer not knocked on the door of Wooden’s mobile home in 2014. The officer—who was not in uniform and did not identify himself as law enforcement—stepped into the home, ostensibly to look for a “fugitive” wanted for misdemeanor theft. Wooden claims he entered without consent, which the officer contests. Either way, when the officer entered (without a warrant), he saw that Wooden had a rifle and arrested him for being a “felon in possession” in violation of state law.

Although these state charges got dropped, federal prosecutors took an interest in the case. They persuaded a jury to convict Wooden for violating a federal law barring people with felony convictions from owning firearms. The probation office first recommended a sentence of 21 to 27 months. But then prosecutors hatched a plot: They would use the Armed Career Criminal Act, or ACCA, to make Wooden’s sentence roughly eight times longer.

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A notorious product of the “tough on crime” era, ACCA requires judges to impose a minimum sentence of 15 years (with a maximum sentence of life) for people with felony convictions in possession of a gun. An individual qualifies for ACCA’s enhancement if they have three prior convictions for violent felonies ​​“committed on occasions different from one another.” Wooden only broke the law on one previous occasion, the 1997 burglary. But prosecutors argued that this crime was actually 10 separate “occasions”—one for each unit he broke into. The judge agreed, and rather than a two-year stint behind bars, he gave Wooden a term of nearly 16 years in prison. A federal appeals court affirmed the sentence.

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In 2020, Wooden appealed to the Supreme Court in forma pauperis, meaning he did not have to pay the regular fees because he is indigent. He mailed in his typewritten petition from the Arkansas prison where he is currently serving his sixth year. It appears he had little help from a lawyer—certainly not from the elite attorneys who typically write petitions that catch the court’s eye. Yet SCOTUS plucked Wooden’s appeal from a pile of thousands, granting his case to decide if a single crime spree counts as multiple “occasions” under ACCA. And, on Monday, the court emphatically rejected this notion of a “one-day career criminal” in a 9–0 ruling. Justice Elena Kagan’s opinion for the court asked “how an ordinary person (a reporter; a police officer; yes, even a lawyer) might describe Wooden’s ten burglaries—and how she would not.”

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An observer, Kagan explained, might say: “Wooden burglarized ten units in a storage facility.” She would not say: “On ten occasions, Wooden burglarized a unit in the facility.” Anyone “using language in its normal way” would group all 10 break-ins together, “as happening on a single occasion.” The justice illustrated this point with a classic Kagan hypothetical. A wedding, she wrote, “often includes a ceremony, cocktail hour, dinner, and dancing.” These activities are “part of a single event,” but “they do not occur at the same moment: The newlyweds would surely take offense if a guest organized a conga line in the middle of their vows.” That’s because an “occasion” may “encompass a number of non-simultaneous activities”—as did the “occasion” of Wooden’s burglary.

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Kagan cited another reason for this interpretation: Congress already considered and rejected the alternative reading. In 1988, after a man named Samuel Petty was sentenced under ACCA for robbing six people during a single stickup, lawmakers amended the statute to clarify that they meant separate criminal episodes. The government’s reading of the law in Wooden would essentially repeal that amendment. This reasoning irked Justice Amy Coney Barrett, who wrote a concurrence rejecting Kagan’s acknowledgment of the legislative history and “purpose” of the law. Joined by Justice Clarence Thomas, Barrett complained that Kagan’s “flawed inference” was “really a bridge too far” and “not how statutory interpretation is supposed to work.” In a classic textualist flourish, she declared that she “would impute to Congress only what can fairly be imputed to it: the words of the statute.”

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The biggest side-squabble revolved around an issue that Kagan didn’t even address: the rule of lenity, which requires courts to interpret ambiguous criminal laws in favor of the defendant. In another concurrence, Justice Neil Gorsuch, joined largely by Justice Sonia Sotomayor, argued for a revival of this rule, which SCOTUS has applied sparingly and inconsistently for decades. When a criminal statute fails to “afford ordinary people fair notice of its demands,” he wrote, “reasonable doubts about its application” should “be resolved in favor of liberty.” This opinion spurred Justice Brett Kavanaugh to write his own concurrence rejecting the rule of lenity while endorsing a requirement of “proof that the defendant was aware that his conduct was unlawful.”

In his final footnote, Gorsuch also noted that “a constitutional question simmers beneath the surface of today’s case.” Under the Fifth and Sixth Amendments, any fact that increases the penalty for a crime must be found by a jury beyond a reasonable doubt. But ACCA tasks judges with deciding—by a mere preponderance of the evidence—whether a defendant committed violent felonies on three previous “occasions.” It is therefore difficult to see how the law’s reliance on judicial fact-finding comports with the Constitution. On Monday, though, there was no need to address this quandary, because the court overturned Wooden’s sentence on the basis of the text alone.

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Monday’s well-reasoned decision throws the Supreme Court’s usual dysfunction into sharp relief. Imagine if it approached every dispute as rationally and impartially as it took on ACCA in Wooden. There would be no outcome-driven crusades to sabotage fair elections, no anti-textual assaults on the government’s ability to function. That’s not the court we have, and it’s not the court we’ll get as long as nine people have unlimited authority to spend a lifetime shaping the law. Monday’s rare repudiation of a manifestation of injustice should not obscure the deeper sickness in our system. The justices’ lofty talk of liberty overlooks one fact: Freedom cannot flourish when those with the greatest power face the least accountability.

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