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A Six-Pack of Beer Might Close a Constitutional Loophole

July 28, 2026
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A Six-Pack of Beer Might Close a Constitutional Loophole

Ken Jouppi has wanted to fly since boyhood. He fixed up Boeing B-52s as an Air Force mechanic, earned his pilot’s license in the late 1960s and moved to Alaska, where he made his living flying a one-man air taxi, KenAir, over some of the emptiest country in America.

In 2012, Mr. Jouppi agreed to fly a woman up north, to Beaver, a village of fewer than a hundred people, to visit her husband. He loaded her luggage and groceries into his plane. But before they could take off, troopers searched the compartment and found a six-pack of beer, clearly visible. Alcohol is banned in Beaver, so they charged Mr. Jouppi, his company and the passenger with importing alcohol into a dry village.

Mr. Jouppi claims he didn’t see the beer, but a jury convicted him of a misdemeanor anyway, and the judge gave him three days in jail and a $1,500 fine — the minimum sentence. But because Alaska law says that bootleggers have to forfeit any airplane used to smuggle alcohol, the prosecutors then tried to seize his plane, a 1969 Cessna, worth about $95,000.

Mr. Jouppi has been fighting to keep the plane ever since. Last week, the Supreme Court agreed to take up his case to answer an important and neglected question: When is a fine so excessive that it becomes unconstitutional?

The Eighth Amendment forbids “excessive fines.” The Supreme Court has defined that term exactly once, in 1998. A fine is unconstitutional when it is “grossly disproportional to the gravity of a defendant’s offense,” the court held in United States v. Bajakajian. In 2019, the court confirmed that the Eighth Amendment restricts not just the federal government from imposing excessive fines, but also states, cities and counties. That is nearly the whole of the doctrine, and the lower courts have split over what “the gravity of a defendant’s offense” means. The justices now can create the yardstick every court must use before calling a punishment excessive.

Ask what Mr. Jouppi did, and the confiscation of the plane looks wildly out of scale. Ask how serious alcohol smuggling is in the abstract, and he loses before the facts are heard. Alaska’s struggle with rural alcohol abuse is real and grievous. Mr. Jouppi was a professional pilot who, a trooper testified, would “have to be blind not to know” what he was loading. Weighing the harms alcohol visits on rural villages — crime, alcoholism, fetal alcohol spectrum disorders, death — the court concluded that “the illegal importation of even a six-pack of beer causes grave societal harm.”

Mr. Jouppi has a legitimate defense. He was a first-time offender, convicted of a misdemeanor over a customer’s beer and given the lightest sentence the law allows. To take a $95,000 airplane on those facts is the very picture of a punishment that does not fit the crime.

The Supreme Court has spent three decades reining in excessive punishments, just not under the Eighth Amendment. The court’s decisions have come under the 14th Amendment’s due process clause, in cases about punitive damages, and the beneficiaries have overwhelmingly been corporations. In one case, the court threw out a multimillion-dollar award against BMW, which had sold a repainted car as new, by evaluating the conduct’s reprehensibility, comparable penalties and the ratio between punishment and harm. Another ruling for State Farm suggested that punitive awards more than nine or 10 times a victim’s actual losses will rarely survive. And a decision in favor of the cigarette company Philip Morris added a rule that reads as if written for Mr. Jouppi: A state may not punish a defendant for harm to people who are not before the court.

Unfortunately for Mr. Jouppi, those rulings do not apply directly to his Eighth Amendment claim. But their insight should. Corporations — BMW, State Farm and Philip Morris — got individualized review and protection from being charged with society’s wider wounds. An 82-year-old pilot, invoking the one clause the Constitution devotes to excessive economic punishment, had the harms of statewide alcoholism laid at his feet.

Since those punitive-damages rulings are civil and Mr. Jouppi’s forfeiture is criminal, they travel on different constitutional tracks. Even so, the gap is hard to unsee, and there is nothing partisan in naming it. The justices most alarmed by aggressive fines and forfeitures span the court’s ideological spectrum, from Justices Neil Gorsuch and Clarence Thomas to Justice Sonia Sotomayor. Their concern is practical: When governments lean on fines and forfeitures for revenue, the burden falls hardest on those least able to fight back.

The justices need not minimize Alaska’s grave concerns about alcohol to hold that this forfeiture went too far. They need only say that fines must reflect the seriousness of a defendant’s actual offense, not the broadest social problem the legislature was trying to address.

The case comes down to a single question: Who decides how grave an offense is — Alaska’s legislature writing a law intended for the worst imaginable alcohol smuggler, or a judge looking at the man in the actual case?

However the justices answer in the coming term, they will tell us whether the Eighth Amendment means as much for a pilot in Alaska as due process has come to mean for BMW.

James J. Sample is a law professor at Hofstra University and the author of the Substack Who Decides Who Decides?

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The post A Six-Pack of Beer Might Close a Constitutional Loophole appeared first on New York Times.

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