Jon Lester has announced his retirement from baseball, ending the run of one of the best pitchers of the past decade. Of course, Lester spent a good portion of his career in Chicago, but he is also beloved for his work with the Boston Red Sox. 

Lester had a 16-year career in the major leagues and will go down as being one of the best postseason pitchers of all time. The lefty always seemed to shine brightest on the biggest stages, including when he was wearing a Chicago Cubs uniform. 

The Cubs certainly had an extremely talented team when they went on to win the World Series in 2016, but they could always count on Lester to set the tone. The 2015 season didn’t go exceptionally well for Lester in the first few starts, but he was rock solid after that point.

It’s a shame that Lester had to finish up his career in St. Louis, and his year ended with COVID-19. A career this strong should have ended on the mound in a World Series, preferably in a Cubs uniform. 

After spending six years with the Chicago Vubs, Jon Lester finished his career with the St. Louis Cardinals.


Most Important Free Agent Ever


Chicago Cubs fans are often credited for being the most optimistic fans in all of sports, but even those fans were struggling with what was going on in Chicago. The Cubs were going through a long rebuild, and it was starting to get harder and harder to believe in what Theo Epstein was selling.

That was not the case for Lester, as he completely bought into the plan and vision of Epstein, and he recognized the talent in the franchise. When Lester agreed to come to Chicago as a free agent, everything changed for the better.

Even if Lester would have gone on to simply be average during his time in Chicago, his signing was the most important thing to ever happen to the Cubs. He paved the way for other free agents to join him, and he brought a winning mindset to the club.

You can expect to see the Cubs honor Lester in some way moving forward, and he will always be remembered for choosing the Cubs when no one else would. 


A Potential Coach?


There was no denying the positive impact Lester had on his teammates and the entire clubhouse, leading to some obvious questions. Since Lester was such a positive presence, some believe that he would eventually turn into a great coach.

Lester was immediately asked about life after retirement, and it doesn’t sound like he will be stepping into a dugout anytime soon. You can expect to see Lester in Arizona for Spring Training, but it’s not going to be turning into a full-time role at this time.

As long as David Ross is the manager in Chicago, you can expect to see Lester around the team at least in some capacity. For now, it might simply be providing some guidance or a word of encouragement on some random visits.