Chicago Cubs: Old friend Jon Lester reaches 200 wins with St. Louis

Can I have “things that make Chicago Cubs fans vomit” for 200? Our old pal Jon Lester finally got to 200 wins in his lengthy big league career. The bad news is it came as a member of the Cubs’ hated rivals, the St. Louis Cardinals, in a win that officially quashed the North Sider’s long dead postseason chances. In a year where everything seemed to go wrong, the universe found one final way to laugh at the Cubs.

Since going to St. Louis, Lester has been part of a massive turnaround that sees the Cardinals in the driver’s seat for the second wild card with a 10-game winning streak, to boot. He’s turned back the clock with the Redbirds, posting a stellar 2.76 ERA over his last eight starts and turning Cubs fans’ stomachs everywhere.

In all seriousness though, it’s a special milestone for one of the best lefty starters of his era and an all-time great in Chicago. We’re in a time where wins are increasingly defunct, but the fact remains that it requires remarkable durability to achieve such a feat. For as frustrating as this all is after Lester expressed interest in returning to the Cubs for a proper sendoff in 2021, I can’t help but feel happy for him and I want to focus on the gravity of such an accomplishment.

Old Chicago Cubs friend Jon Lester reached a huge milestone… as a Cardinal

Lester’s 200 wins put him among only 118 other pitchers that have reached the mark, many of whom are in Cooperstown. He did this despite having his career nearly derailed early on by a non-Hodgkin’s lymphoma diagnosis and a shortened, difficult 2020 season. The fact is, Lester accomplished this feat by simply being a solid, reliable and oftentimes stellar starter for pretty much the entirety of his career.

Of his contemporaries still pitching today, only two others have made it to the milestone so far: Justin Verlander and Zack Greinke. In five full and one partial season with the Cubs, Lester left it all on the field, racking up 77 of his 200 wins on the North Side and pitching more than 1,000 regular-season innings with a very solid 3.64 ERA through it all. He started in Chicago at age 31 and kept up that workhorse mentality he’d gained as a young star in Boston annually, even when his production inevitably waned and fatigue got the best of him.

There’s sure to be some bitterness that Tom Ricketts couldn’t (or wouldn’t) bring Lester back for one last ride so he could make history in the Friendly Confines and receive a proper sendoff. The fact that this happened with the Cardinals makes that pill even harder to swallow.

Still, even as old Lefthander came back on the field to hug his Redbird teammates, I felt only happiness that one of the greatest to pitch in a Cubs uniform reached another mark to put him among legends.