Reflecting on Jon Lester’s tremendous legacy with the Chicago Cubs

After 16 seasons, 200 career wins and a trio of World Series championships, Chicago Cubs legend Jon Lester has decided to call it a career. The five-time All-Star announced early Wednesday morning that it was time for him to step away from the game.

For Cubs fans, like myself, after the news broke, it really took me back and made me reflect on the big left-hander’s career. More specifically, to ponder his six-year tenure on the North Side.

Let me make this clear and obvious: Lester is the greatest free agent signing in Chicago sports history. What he did for the franchise still has a lasting impact to this day. Lester coming here back in 2015 was a spark that ignited the fire that changed everything.

Back in December 2014, Lester (who was a top free agent) decided to take a gamble and sign with a rebuilding Chicago Cubs team. He saw the young pieces that were in place for the future and felt that the North Side was his best opportunity to win in the long run. Sure enough, his gamble paid off, and he wound up winning his third World Series ring two years into the contract.

When you look at what Lester did, he is really the pioneer of what a lot of veterans do in modern days sports. A veteran deciding to sign with a young team and helping build success that will lead to championships.

Not only that, Lester was a *bleeping* gamer for the Cubs. Whenever the team needed a big start – whether it be the regular season or postseason – you could almost always rely on Lester to get the job done.

A game I always think back to where he truly shined was in 2018 in the NL Wild Card Game at Wrigley Field. Even though the Cubs did not end up winning the game, Lester pitched like his life was on the line and did everything he could to try and push Chicago to victory. He pitched with a grit and an attitude that is hard to find across baseball.

Without Jon Lester, the Chicago Cubs don’t erase that 3-1 World Series deficit

Obviously, the World Series hits home more than anything. Game 5 of the World Series will forever be one of the greatest pitching performances I have ever watched because of what was at stake. With the Cubs’ season at the brink against the Indians, Lester went out and did everything he could for the Cubs season to last another day. Lester went six gut-wrenching innings, only giving up one run while striking out four.

Then, on short relief, Lester came into a sloppy situation in Game 7. Even though he got into a little bit of trouble in his first inning of relief of Kyle Hendricks, Lester settled down nicely and was able to hand the ball off with a “comfortable” lead. The southpaw was a warrior and he would’ve done anything to help his team win.

Lester will forever be a Chicago legend for what he did for the city, the organization and its fans. He delivered on his promise of bringing a World Series and had six amazing years with the Cubbies. One day his number 34 (also Kerry Wood’s) should be flying from the foul pole at the Friendly Confines.

So Chicago, raise your Miller Lites and toast Big Jon today. Lester changed Cubs history that fateful day in December 2014 and should be appreciated and acknowledged for that. Hope you enjoy every minute of retirement, Jon – you certainly deserve it.