Chicago Cubs Rumors: Jon Lester mulling retirement at season’s end

We live in strange, strange times. Javier Baez and Anthony Rizzo now call New York home, we just experienced an emotional weekend where now-San Francisco Giants star Kris Bryant made his return to Wrigley Field and another Chicago Cubs fan favorite, Jon Lester, is doing what he can to help propel the St. Louis Cardinals to the postseason.

The fact Lester was traded to St. Louis at the deadline was largely overlooked given the number and magnitude of moves the Cubs made, but the 37-year-old southpaw has now made eight starts for the Redbirds down the stretch.

At this point in his career, he’s a far cry from what he once was. For the last three or so years, Lester has been a back-end innings-eater and little more. Since the start of the 2019 season, he carries a 4.68 ERA/4.80 FIP across 67 starts spanning 352 innings. This year between St. Louis and Washington, he’s averaging just 5.4 strikeouts per nine – the lowest mark of his career.

Given he turns 38 in January and has lacked the signature effectiveness and reliability that once made him one of the surest arms in all baseball, though, the future is now seemingly uncertain for Lester.

Regardless of what the future holds, all Lester and the Cardinals are focused on is the coming weeks. St. Louis is in the thick of the NL Wild Card race, entering action Sunday just two games out of the final postseason spot in the Senior Circuit. As Cubs fans are all too familiar with, Lester could end up being a difference-maker down the stretch. This is a guy who thrives in big games and dramatic moments and that hasn’t changed with time.

Chicago Cubs: Jon Lester had some remarkable years on the North Side

Lester’s arrival in Chicago prior to the 2015 season was a booming declaration to the rest of the league: the Chicago Cubs were ready to make some noise – and, boy, did they ever.

In his first year with the team, the southpaw anchored the rotation, eclipsing 200 innings as the Cubs made an improbable run to the NLCS before getting steamrolled by the New York Mets. That next season, of course, was historic, with Chicago winning its first World Series championship in 108 years – and Lester playing a key role.

Finishing as runner-up in National League Cy Young voting, Lester won 19 games in 2016 with a league-leading .792 winning percentage. Come October, he did what he does best: dominate. Lester shared NLCS MVP honors with Javier Baez and made some big-time appearances in the Fall Classic, including coming out of the bullpen on short rest in Game 7.

Due to COVID-19, Lester never got to walk off the mound one last time at Wrigley Field to a standing ovation. Instead, he struggled through his final year with the team before unceremoniously departing in free agency, despite saying he’d have returned to the Cubs for virtually anything.

With the Cubs out of contention this year, we can keep an eye on Lester in St. Louis, seeing if he might have just enough left in the tank for one last October run. If this is the end of the road, it’s been a tremendous career for the five-time All-Star and three-time World Series champ.