Should the fine have to fit the crime?

The U.S. Constitution famously outlaws “cruel and unusual punishments.” But there's another, far more obscure part of the Constitution called the Excessive Fines Clause, which basically says that the fine has to fit the crime. So far, the Supreme Court has been pretty mysterious about what that means. But for Ken Jouppi, the fate of his $95,000 plane hinges on it.

Ken is a bush pilot. He used to run an air taxi service in Fairbanks, Alaska. In 2012, police caught one of Ken’s passengers with a six-pack of Budweiser in her luggage. Over that six-pack, Ken was convic...