9. Johan Santana, 139 wins, 136 ERA+, 2,025 2/3 innings, 1,988 strikeouts, 51.6 bWAR
This could be controversial to have him so high, but for many, there was not a better left-handed pitcher than Santana in the game at his peak, and that is saying something, considering a lefty that figures very prominently later in this list was still very active during Santana’s career. The story of his incredibly humble roots to his career makes his career story all the better.
Originally signed out of Venezuela by the Houston Astros, Santana was selected by the Marlins in the Rule 5 draft in 1999, but the Minnesota Twins traded with the Marlins to acquire his rights. Santana would spend his 2000 season as a seldom-used long reliever and spot starter, and then returned to the minor leagues, making his way back for another long relief role in 2001.
In 2002, Santana was one of the most dominant pitchers in the American League, and he repeated the feat in 2003, both while working as a long reliever. Then Johan’s 2004 happened. He won 20, led the AL in ERA, and led the AL in strikeouts.
Sanatana had quickly gone from one of the best left-handed pitchers in the American League, to one of the best left-handed pitchers in all of baseball, and by the time 2008 was completed, the discussion was where he ranked among the best left-handed pitchers in the history of the game.
However, it was after that 2008 season that his career went South. He made just 25 starts in 2009, returned to make 29 starts in 2010, including the first no-hitter in New York Mets team history, and then missed all of the 2011 season before coming back for one last attempt in 2012.
His shoulder was gone, and with it his career, a player who lived off his changeup, relying on his shoulder. He was selected to 4 All-Star games, won 2 Cy Young Awards, received Cy Young votes in 6 seasons, won a Gold Glove, and won the 2006 American League pitching triple crown.
Next: 8. The Left Arm of God