Jon Lester has retired

MLB Rumors: Jon Lester, the lefthanded starting pitcher who was part of championship teams for the Boston Red Sox and the Chicago Cubs, has retired, per multiple reports.

Lester, 38, won championships with the Boston Red Sox in 2007 and 2013, while also being a key part of the 2016 Chicago Cubs championship team that broke the Curse of the Billy Goat and brought a title to Wrigley Field for the first time in over a century. Lester also had a brief stint with the Oakland A’s in 2014, and spent the 2021 season pitching for the St. Louis Cardinals and the Washington Nationals.

For Rangers fans, Lester is a reminder of what could have been, as after the 2003 season the Rangers and Red Sox had agreed to a trade that would have sent Alex Rodriguez to the Red Sox for Manny Ramirez and Lester, then a 19 year old who had been drafted in the second round in 2002. The trade didn’t go through because the MLBPA would not sign off on ARod’s restructuring of his contract — which would have lowered its value — and so Lester stayed with Boston, and Texas instead ended up shipping Rodriguez out for Alfonso Soriano and Joaquin Arias.

Lester has had a very solid career, posting a career 3.66 ERA — including a 3.64 ERA in 241 starts for the Red Sox and a 3.64 ERA in 171 starts for the Cubs — with a career 200-117 records. I am going to be interested in seeing how his Hall of Fame case plays out down the road. He doesn’t have the big milestones one would expect from a Hall of Fame pitcher — he was a five time All Star, received Cy Young votes in just four seasons (finishing 2nd, 4th twice, and 9th), and his only notable appearance at the top of the league leader boards was in 2018, when he led the National League in wins.

However, Lester also was seen as a big time, big game pitcher, someone you want taking the ball in Game 1 in an October series. Winning championships with the Red Sox and Cubs will get you bonus points, and his overall postseason performance — a 2.51 ERA in 154 innings — was exceptional. So I could see Lester having a Jack Morris type of candidacy (Lester has a career bWAR of 44.3, Morris 43.6), getting a decent amount of support on the writers’ ballots due to his reputation and aura, even if the numbers aren’t quite there.

Regardless, Lester has had a great career, and is celebrated by two different fanatical fanbases. Congratulations to him, and best of luck in his post-playing career.