The 30 greatest left-handed pitchers in MLB history

Greatest LHPs in MLB history: 27. Jon Lester

• 2,397 strikeouts
• 3.60 career ERA
• 44.6 career WAR

Jon Lester and Andy Pettitte are very similar baseball players when you look at the trajectory of their career. Both are decorated winners, with Pettitte winning five World Series and Lester winning three (thus far) in his career.

Pettitte made three all-star teams, Lester has made five in his career. Pettitte won that ALCS MVP, Lester has the 2016 NLCS MVP to his name. Neither were ever in that elite tier of pitching, but they were as consistent as it comes and always provided valuable innings pitched.

Lester started 30 or more games in every single season from 2008 through 2019 and was on pace to start 30 games if there was a 162-game season in 2020. He has received Cy Young votes four times in his career, finishing fourth twice and second once.

From 2008 through 2018, Lester ranked second in starts behind Justin Verlander and fourth in total innings pitched. He ranked sixth in strikeouts and had the third-most among southpaws in that timeframe.

And he is one of the best postseason pitchers of all-time. Lester has a career 2.51 postseason ERA and has thrown 154 innings in the postseason.

Lester is 37 years old at the time of writing this and has signed a one-year deal with the Washington Nationals. It is unclear if the 2021 season is the last of his career.