RHP, 1876-1947. Set a modern day Major League record in 1905 when he lost 29 games in a single season. RHP, b. 1944. These players both served time in jail. Wilson, born in Scotland, was a star in Pennsylvania politics for two decades before being named to the Court in 1789. He wrote few opinions, nearly all of little import, though, and failed to match the promise of his earlier public career. His mismanaged investments, and dealings with creditors earned him two jail terms. McLain is baseball’s last 30-game winner; he went 31-6 for the 1968 World Champion Tigers. His post-career troubles included a conviction on racketeering and cocaine charges, which landed him in jail for over two years in the 1980s. RHP, 1874-1909. Won 41 games in 1904, but is perhaps most remembered that year for his wild pitch on the last day of the season, which cost the NY Highlanders the pennant. RHP, b. 1956. Compiled an amazing .941 winning percentage (16 wins versus only 1 loss) with the Cubs in 1984.