Bush pilot Ken Jouppi lost his Cessna after a passenger unknowingly carried alcohol into a dry village, resulting in a bootlegging conviction and mandatory forfeiture of his aircraft. What followed was a 12-year fight over whether such a penalty violates the Eighth Amendment’s Excessive Fines Clause. This constitutional provision, meant to ensure punishments fit the crime, has been inconsistently applied—especially during the war on drugs, when asset forfeiture became a widespread enforcement tool. A landmark 1998 Supreme Court case ruled that seizing $300,000 from a man who failed to report cash was unconstitutionally excessive, setting a precedent for proportionality. Yet many courts still allow disproportionate penalties, often due to systemic reliance on fines as revenue and judicial hesitation. Ken’s case could force the Supreme Court to clarify how far governments can go in imposing financial punishments, challenging a model where justice systems profit from penalties.