16. Denny McLain
Charges: Drug trafficking, embezzlement, money laundering, mail fraud
Number Of Arrests: 4
McLain was a good pitcher in his day, winning 31 games in 1968. But he had a big gambling problem. It got so bad he decided to start a gambling ring because of all the money he was losing. He was suspended from baseball in 1970. Strapped for cash, the Tiger great tried his hand at slinging snow. He was arrested for trying to sell three kilos of cocaing and sentenced to 23 years in 1985.