JA, New York
Punishment: $10,000 fine.
JA made headlines in the late '80s when he was sued by the city for doing a bunch of subway cars and signs along the Henry Hudson parkway. According to Newsday, "Police sources remember the Koch administration picking on JA because of his father's celebrity." Even at a time when the city had decided it wasn't worth it to sue writers for damages (SANE/SMITH excepted), under David Dinkins' mayorship, JA was fined at least $10,000 dollars to set a public example.