Cubs: Ranking the five best moves during the Theo Epstein era

Cubs: Theo Epstein’s Greatest Moves: No. 1 – Signing Jon Lester

Theo Epstein had to sell Jon Lester on what he was building in Chicago. His pitch to the coveted left-hander included a presentation of him on the mound with a Cubs’ World Series title at stake. Less than two years later, that came to fruition with Lester coming out of the pen in Game 7 in Cleveland.

While his win-loss record in 2015 wasn’t what you’d like, he proved that’s not how you measure success with pitchers. He worked to a 2.92 FIP across 205 innings, cementing himself atop the rotation. He followed that up with a runner-up finish in the NL Cy Young voting in 2016 – adding a third World Series ring to his collection.

Although he’s certainly not the pitcher he was back at the start of his Cubs tenure, Lester has continued to reinvent himself on the bump. There are few better big-game pitchers in baseball today and, when October comes around, he’s the guy you want to have the ball.

Over 1,000 innings of regular season action, a pristine postseason resume, two All-Star appearances and a World Series title. The Cubs got exactly what they were hoping for in Lester – and it’s clear he’s not just the best move Theo Epstein made here, but one of the all-time best free agent signings in Chicago sports history.