Today is the first Monday in October, which means the United States Supreme Court is beginning a new term. By law, the Court’s annual term opens on the first Monday in October, a tradition that reliably brings a fresh collection of constitutional questions, statutory disputes, and lawyers attempting to explain very complicated things while nine justices interrupt them.

Over more than two centuries, the Supreme Court has decided cases involving presidential power, slavery, war, religious liberty, property rights, interstate commerce, and the meaning of the Constitution.

It has also decided whether a tomato is legally a vegetable, whether an airplane is a motor vehicle, how much legal protection an owner has in an unlicensed dog, whether professional baseball is interstate commerce, and whether frightened chickens can establish a claim under the Fifth Amendment.

This is not evidence that the justices occasionally became bored and started pulling legal questions from a hat. Each of these cases involved a genuine dispute about federal statutes, constitutional rights, government power, or private property. The facts simply arrived dressed as a legal fever dream.

The cases are not the only surprising part of Supreme Court history. The justices themselves have occasionally wandered well beyond the ordinary job description—running for governor while still on the bench, prosecuting Nazi war criminals at Nuremberg, investigating Pearl Harbor, and chairing the Warren Commission. We previously explored some of those judicial extracurricular activities in “Supreme Court Justices With Side Jobs: When the High Court Moonlighted.” Apparently, a lifetime appointment to the nation’s highest court has not always been enough to keep an ambitious résumé from getting restless.

And strange legal disputes are hardly unique to the United States. England once discovered, rather awkwardly, that trial by combat was still technically available in 1818. The law has a remarkable ability to preserve old rules until someone finally asks whether anybody remembered to get rid of them.

So, in honor of the opening of a new Supreme Court term, here are eleven of the strangest Supreme Court cases of the nineteenth and early twentieth centuries—an era when a minister, a tomato, a baseball team, an airplane, and approximately 150 extremely nervous chickens all managed to contribute something to American law.

United States v. Kirby: Can You Arrest the Mailman for Murder?

Our story begins in 1868 with United States v. Kirby, a case presenting a legal question that Congress probably had not anticipated when it passed a law against obstructing the mail.

A Kentucky sheriff named Kirby had a perfectly legitimate warrant for the arrest of Farris, who had been indicted for murder. There was one complication. Farris was carrying the United States mail aboard the steamboat General Buell.

Kirby boarded the boat with a posse, arrested Farris, and temporarily delayed both the steamer and the mail. Federal prosecutors responded by charging Kirby and his assistants under a statute making it a crime to knowingly and willfully obstruct or retard the passage of the mail or its carrier.

Read literally, the statute seemed to create an interesting problem. The sheriff had obstructed the mail. He had done so intentionally. Apparently the question was whether federal postal efficiency required Kentucky to leave an accused murderer alone until he finished his route.

The Supreme Court decided that Congress could not possibly have intended such a result. Justice Stephen Field explained that statutes should not be interpreted in ways producing absurd consequences plainly outside the legislature’s purpose.

To illustrate the point, he invoked an old example involving a law that punished anyone who drew blood in the street. Nobody, he observed, would apply it to a surgeon who opened the vein of a person who collapsed in the street. Likewise, a law against obstructing the mail did not immunize a mail carrier from arrest for murder.

The decision gave American statutory interpretation an enduring principle: read the words, certainly, but do not assume Congress intended civilization to stop functioning because nobody included a footnote about homicidal mailmen.

Church of the Holy Trinity v. United States: Congress Accidentally Outlaws Hiring a Minister

In 1885, Congress enacted the Alien Contract Labor Law to restrict employers from importing foreign workers under contracts made before they entered the United States.

Then the Church of the Holy Trinity in New York hired an English clergyman.

The church contracted with the Rev. E. Walpole Warren, who was living in England, to move to New York and become its rector. Federal officials concluded that the agreement violated the statute because Warren was, indisputably, an alien who had agreed to come to the United States to perform “labor or service of any kind.”

The government sued the church, and the case eventually reached the Supreme Court as Church of the Holy Trinity v. United States in 1892.

The awkward part was that the government had a surprisingly strong argument based on the actual words Congress had written. The Court openly acknowledged that hiring the minister fell within the literal language of the statute.

Nevertheless, the justices concluded that Congress had been trying to prevent the importation of contract laborers, particularly manual laborers, rather than to prevent churches from recruiting clergy abroad. The transaction fell within the words of the statute but outside what the Court understood to be its intended purpose.

Holy Trinity became a famous example of courts looking beyond literal wording when a statute’s text appears to produce a result Congress almost certainly never contemplated. It also stands as a useful warning to legislative drafters: “of any kind” is an impressively large category.

Nix v. Hedden: Is a Tomato a Fruit or a Vegetable?

The following year brought Nix v. Hedden, the case that settled one of the great disputes of American history, provided that your definition of “great disputes” includes disagreements normally conducted near the produce aisle.

The Tariff Act of 1883 imposed a duty on imported vegetables but allowed fruits to enter duty-free. John Nix and other produce merchants imported tomatoes into New York, paid the vegetable tariff under protest, and sued the collector of customs.

Their argument was scientifically sound. Botanically, a tomato is a fruit because it develops from the flower of the plant and contains seeds. The same reasoning makes cucumbers, peppers, squash, and pumpkins fruits, proving that botany has been quietly sabotaging the salad bar for generations.

The Supreme Court was unmoved.

The justices concluded that Congress had used “fruit” and “vegetable” according to their ordinary meanings rather than their technical botanical definitions. Tomatoes might be fruits to scientists, but ordinary people served them with dinner rather than dessert and regarded them as vegetables.

The Court therefore unanimously declared tomatoes vegetables for tariff purposes.

Botanists were not required to revise their textbooks. Farmers were not instructed to relocate their tomato plants beside the turnips. The Court merely decided that a tomato could be one thing in science and another thing at customs.

It was statutory interpretation by dinner menu.

Sentell v. New Orleans: How Much Constitutional Protection Does a Dog Get?

In 1897, the Supreme Court turned its attention from produce to dogs.

The unfortunate participant in Sentell v. New Orleans & Carrollton Railroad Company was Countess Lona, a valuable Newfoundland dog registered in the American Kennel Club’s stud book.

While following her owner on a walk through New Orleans, Countess Lona stopped on the railroad tracks and was struck and killed by an electric car. Her owner sued the railroad, and a jury awarded him $250. The Louisiana Court of Appeals reversed, however, holding that he had not shown compliance with the state assessment law and city tagging ordinance. He then took the case to the U.S. Supreme Court.

The case forced the justices to confront the surprisingly philosophical question of what sort of property a dog actually is—and how far a state could condition an owner’s property rights on compliance with taxation and licensing requirements.

The Court held that states had broad authority to regulate dogs and could condition legal protection upon licensing or assessment requirements. In language unlikely to appear in an advertisement for a veterinary clinic, the opinion described dogs as occupying an unusual position between fully domesticated livestock and wild animals.

The Court even discussed their lingering “wolfish instincts,” their tendency to attack sheep, and the existence of dogs that were merely “vicious, noisy, and pestilent.” One suspects the justices had encountered several neighborhood dogs about which they still had strong feelings.

Countess Lona’s case helped define the government’s authority to regulate ownership of animals. It also produced the unusual spectacle of the nation’s highest court examining whether dogs are property while simultaneously sounding rather unconvinced that dogs are entirely respectable citizens.

The Paquete Habana: The Supreme Court Saves Two Fishing Boats

When the United States went to war with Spain in 1898, American naval forces blockaded Cuba. During the blockade, U.S. vessels captured two small Spanish fishing boats—the Paquete Habana and the Lola—and brought them to Key West as prizes of war.

The boats were not warships. They were not carrying weapons, military dispatches, soldiers, or secret agents. They were carrying fish.

Very fresh fish, in fact. The crews stored their catch alive aboard the vessels while returning to Havana, which makes the fish among the comparatively few Supreme Court litigants to arrive at the beginning of the case still swimming.

The government sold the vessels after a lower court condemned them as prizes. The owners appealed, producing the wonderfully named 1900 case The Paquete Habana.

The Supreme Court examined centuries of international practice and concluded that small coastal fishing vessels peacefully pursuing their ordinary work were traditionally exempt from capture during wartime unless they were participating in hostilities or assisting the enemy.

The captures were therefore unlawful.

The case became one of the leading American decisions recognizing customary international law. Generations of law students have consequently encountered a major principle of international jurisprudence through the adventures of two Spanish-flagged fishing smacks out of Havana whose crews primarily wanted to get home before the merchandise spoiled.

United States v. Forty Barrels and Twenty Kegs of Coca-Cola: The Government Takes on Caffeine

Some case names immediately communicate constitutional grandeur. Marbury v. Madison. McCulloch v. Maryland. United States v. Forty Barrels and Twenty Kegs of Coca-Cola.

That last one sounds less like a Supreme Court case than an inventory sheet prepared for an extremely ambitious church picnic.

Federal officials seized 40 barrels and 20 kegs of Coca-Cola syrup shipped from Atlanta to Chattanooga and sought their condemnation under the Pure Food and Drugs Act of 1906. Because the proceeding was brought against the property itself, the containers received top billing in the case caption.

The government argued that the product was adulterated because it contained caffeine, which officials alleged was an added poisonous or deleterious ingredient. It also alleged that the product was misbranded: the name “Coca-Cola,” the government contended, represented the presence of substances derived from coca and cola, while the drink contained “no coca and little if any cola.” Coca-Cola disputed that claim and maintained that its formula did contain substances derived from coca leaves and cola nuts.

The lower courts sided with Coca-Cola, but in 1916 the Supreme Court reversed. It held that caffeine could qualify as an “added ingredient” under the federal law even though it was part of the product’s established formula, and that whether the amount used could be harmful was a factual question for the jury.

The Court also rejected the idea that the name “Coca-Cola” was automatically protected simply because it had become the product’s trade name. If “coca” and “cola” described ingredients that consumers would expect the drink to contain, the product could be misbranded if those ingredients were actually absent—unless the combined name had acquired a secondary meaning identifying the beverage regardless of its ingredients. Because the evidence on those questions was disputed, they too could not be resolved by a directed verdict.

The Supreme Court did not ban Coca-Cola. It did not outlaw caffeine. It sent the case back for further proceedings.

The forty barrels and twenty kegs, having reached the highest court in the United States, presumably declined requests for comment.

Federal Baseball Club v. National League: Baseball Somehow Is Not Interstate Commerce

By 1922, professional baseball teams were located across multiple states. Players routinely traveled across state lines. Teams played scheduled games against opponents in other states. Money moved through an organized national business.

So naturally, the Supreme Court held that professional baseball was not interstate commerce.

The dispute in Federal Baseball Club of Baltimore v. National League arose after the Federal League attempted to compete with the established American and National Leagues. The Baltimore club alleged that the established leagues had conspired to destroy their competitor and sued under federal antitrust laws.

Justice Oliver Wendell Holmes wrote for a unanimous Court that the business at issue consisted of providing baseball exhibitions. The fact that teams had to cross state lines to play those games was, in the Court’s view, merely incidental to the local exhibitions themselves.

Baseball therefore fell outside the federal antitrust laws.

The reasoning became the foundation of baseball’s famous antitrust exemption, an anomaly that the Supreme Court itself later acknowledged had become deeply embedded in the sport’s history.

It is one of those legal rules that makes considerably more sense if you begin with the phrase, “Well, you see, in 1922…” Baseball players could spend the summer traveling from state to state while participating in a national commercial enterprise, but the commerce remained legally local. The trains apparently crossed state lines; baseball itself stayed home.

For another improbable bit of baseball history from the same general era, consider the 17-year-old pitcher who struck out both Babe Ruth and Lou Gehrig. Early twentieth-century baseball was apparently unwilling to do anything in an ordinary manner.

Wickard v. Filburn: The Wheat That Never Left the Farm but Entered Interstate Commerce Anyway

Twenty years later, the Court further complicated its interpretation of interstate commerce when it tackled the weedy issue of wheat production.

Roscoe Filburn operated a farm in Ohio where he raised livestock, poultry, and winter wheat. Federal agricultural regulations limited how much wheat he could produce during the government’s effort to control national supply and stabilize prices.

Filburn was allotted 11.1 acres.

He planted 23.

The excess produced 239 bushels of wheat. Filburn argued that much of it was intended for use on his own farm—to feed animals, supply his household, and provide seed for future planting.

The wheat had not crossed a state line. It had not even left the farm. It was in Ohio, minding its own agricultural business and probably puzzled by the sudden constitutional attention.

The Supreme Court nevertheless upheld the regulation in Wickard v. Filburn in 1942.

The Court reasoned that wheat grown for personal consumption affected the interstate market because it replaced wheat Filburn might otherwise have purchased. One farmer’s contribution was insignificant, but if large numbers of farmers did the same thing, the aggregate effect on the national wheat market could be substantial.

The wheat therefore fell within Congress’s commerce power even though that particular wheat never entered commerce at all.

Wickard became one of the broadest interpretations of federal power under the Commerce Clause. It also gave generations of law students the initially baffling proposition that although baseball played across multiple state lines was not interstate commerce, an activity that avoided interstate commerce was nonetheless interstate commerce.

If understanding the law was easy, lawyers would be paid minimum wage.

McBoyle v. United States: An Airplane Is Not a Motor Vehicle

In 1931, the Supreme Court encountered a man named William McBoyle, who had caused a stolen Waco airplane to be transported from Illinois to Oklahoma, knowing that it had been stolen.

This was not an especially strong candidate for Citizen of the Year.

The legal difficulty was that federal prosecutors charged McBoyle under the National Motor Vehicle Theft Act. The law prohibited interstate transportation of a stolen “motor vehicle” and defined that phrase to include automobiles, trucks, automobile wagons, motorcycles, and “any other self-propelled vehicle not designed for running on rails.”

An airplane is self-propelled. It is not designed to run on rails. The government therefore argued that the statute covered airplanes.

The Supreme Court unanimously disagreed in McBoyle v. United States.

Justice Holmes acknowledged that “vehicle” could theoretically be used broadly enough to include things moving on land, water, or air. But in ordinary speech, especially alongside automobiles, trucks, wagons, and motorcycles, the word called to mind something that traveled on land.

Criminal laws, Holmes explained, must give people fair warning about what conduct is prohibited. Congress knew airplanes existed when it wrote the statute and had not mentioned them.

McBoyle’s conviction was reversed.

The Court did not discover a constitutional right to transport stolen airplanes across state lines. It merely concluded that prosecutors needed a federal statute that actually covered aircraft. Congress eventually took the hint: in 1945, it amended the National Motor Vehicle Theft Act to expressly include aircraft.

Considering that the Wright brothers had achieved powered flight less than three decades earlier, technology had apparently advanced slightly faster than the United States Code.

United States v. Carolene Products: The Milk Case with the Most Famous Footnote in Constitutional Law

Every field has its celebrities. Constitutional law has presidents, landmark civil-rights decisions, and Footnote Four.

Footnote Four comes from a 1938 Supreme Court case about imitation milk.

The product was called Milnut. It consisted of condensed skim milk blended with coconut oil, which replaced the natural milk fat. Congress had enacted the Filled Milk Act prohibiting interstate shipment of such products on the ground that they imitated ordinary milk while lacking some of its nutritional characteristics.

Carolene Products Company challenged the law, producing United States v. Carolene Products Co..

The Supreme Court upheld the federal statute. Ordinary economic legislation, the Court said, was entitled to a strong presumption of constitutionality when lawmakers could reasonably have believed there was a factual basis for the regulation.

Then came the footnote.

In Footnote Four, Justice Harlan Fiske Stone suggested that this deferential approach might not apply with the same force when legislation conflicted with specific constitutional rights, interfered with democratic processes, or burdened certain minority groups.

The footnote eventually became enormously influential in the development of modern constitutional doctrine, particularly the idea that some laws affecting specific constitutional rights, the political process, or certain minority groups may warrant more searching judicial scrutiny.

Thus one of the most influential footnotes ever written by the Supreme Court appears in a case whose central legal question involved whether Congress could prohibit interstate shipments of coconut oil pretending to be milk.

Constitutional law has never been overly concerned with dramatic presentation.

United States v. Causby: The Chickens That Changed American Airspace

Our tour ends in 1946 with the case that demonstrates why no constitutional law course is truly complete until someone introduces frightened poultry.

Thomas Lee Causby owned a 2.8-acre chicken farm near an airport outside Greensboro, North Carolina. During World War II, the federal government began using the airport for military aircraft.

The planes passed extraordinarily low over Causby’s property. The approved glide path crossed the farm only 83 feet above the ground—67 feet above the house, 63 feet above the barn, and just 18 feet above the tallest tree.

The noise and lights disrupted the family’s sleep and terrified the chickens. Some birds panicked and flew directly into the walls of their enclosures. As many as six to ten died in a single day, and approximately 150 were eventually lost.

Anyone who has ever watched a chicken confront a mildly unexpected garden hose will appreciate that repeated passes by low-flying military aircraft were unlikely to improve flock morale.

Causby argued that the government had effectively taken part of his property without paying compensation. The government responded that aircraft traveled through public airspace and had never physically occupied the farm.

The Supreme Court’s decision in United States v. Causby helped define property rights in the age of aviation.

The Court rejected the ancient common-law notion that land ownership extended indefinitely upward. That idea was workable when the principal traffic above a farm consisted of birds, clouds, and the occasional ambitious church steeple. Commercial aviation made it untenable. Otherwise, the Court observed, every transcontinental flight could produce countless trespass claims.

But the government did not have unlimited freedom to fly directly over private property at any altitude it pleased. Flights that were so low and frequent that they directly interfered with the owner’s use of the land could amount to a taking requiring compensation under the Fifth Amendment.

Causby therefore had a constitutional claim.

The case helped establish the modern legal boundary between public airspace and private property. It also confirmed that, under sufficiently persistent circumstances, dead chickens can make constitutional law.

Why the Strangest Supreme Court Cases Matter

It is easy to treat these decisions as legal trivia: a mail carrier accused of murder, an imported minister, tomatoes, an unfortunate Newfoundland dog, Spanish-flagged fishing boats, Coca-Cola barrels, baseball teams, stolen airplanes, imitation milk, homegrown wheat, and chickens with an understandable aversion to military aviation.

But the strange facts are precisely what make the cases useful.

Legal principles sound neat when stated in the abstract. Congress may regulate interstate commerce. Criminal statutes must give fair notice. Government must compensate people when it takes private property. Laws should be interpreted according to their text and purpose. International law can become part of the law courts apply.

The interesting part begins when somebody asks what those principles actually mean outside the textbook.

Does a law against obstructing the mail prevent a sheriff from arresting the mail carrier for murder? Is a tomato a fruit when the tax collector arrives? Does interstate commerce include baseball teams that repeatedly travel interstate to conduct their business? Is an airplane included in a criminal law written about automobiles? Can Congress regulate wheat that never leaves a farm? How low can an airplane fly before the government has effectively taken part of the land underneath it?

The strangest Supreme Court cases exist because the answer is not obvious—or because it is obvious to everyone involved, but unfortunately obvious in opposite directions.

That may be the enduring peculiarity of American law. Monumental legal doctrines rarely arrive at the courthouse dressed for the occasion. More often, they show up carrying a tomato, piloting a stolen airplane, arguing over coconut oil, or trying to persuade the Supreme Court to do something about the chickens.

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