46. Lefty Gomez
Lefty Gomez is one of the greatest winning pitchers in MLB history, as he led the New York Yankees to World Series titles in five of his 13 seasons with the club. Gomez won six of his seven career postseason starts and was a huge reason why the Yankees won four straight World Series’ from 1936 through 1939. Gomez also won two Triple Crowns in 1934 and 1937, along with winning the Cy Young in those years as well.