Chris Drury (NHL)
When: 1989, Trumbull, Conn.
When he went pro: Drury has a truly unique claim to fame: He’s the only man to win a Little League World Series and also have his name etched on the Stanley Cup. After pitching Trumbull to glory in Williamsport in 1989, Drury went on to win the Stanley Cup with the Colorado Avalanche (in 2001) and, eventually, earn induction into the Hockey Hall of Fame in 2015. Not a bad career, eh?