Chicago Cubs legend Jon Lester is riding off into the sunset

Inarguably the greatest free agent signing in Chicago Cubs history and among the best in Chicago sports history, as a whole, Jon Lester is riding off into the sunset after 16 years in the big leagues.

"“It’s kind of run its course,” Lester said. “It’s getting harder for me physically. The little things that come up throughout the year turned into bigger things that hinder your performance … I’d like to think I’m a halfway decent self-evaluator. I don’t want someone else telling me I can’t do this anymore. I want to be able to hand my jersey over and say, ‘Thank you, it’s been fun.’ That’s probably the biggest deciding factor.”"

Lester, who won his 200th game this summer, has a resume that will certainly garner Cooperstown consideration. Three World Series rings, co-NLCS MVP in 2016, five All-Star appearances and over 2,700 regular season innings to his credit. When the pressure was high, the left-hander was at his best – as Cubs fans learned during his time on the North Side.

In December 2014, Lester signed what was at the time, the richest free agent pact in team history, a six-year, $155 million deal to join a Cubs team coming off a 73-win season. But in his first year in Chicago, he helped the organization turn a corner. With Lester, a young core and new manager Joe Maddon, the Cubs made an improbable run to the NLCS – taking down the division rival Pirates and Cardinals in the process.

Chicago Cubs: Without Jon Lester, there is no World Series championship

Of course, we all know what happened in 2016. Lester finished runner-up in National League Cy Young voting after going 19-5 with a 2.44 ERA across 202 2/3 innings of work. His .792 winning percentage led the league and it marked the ninth time in 10 years he eclipsed that 200-inning mark.

The dynasty we all envisioned after that season never materialized. Lester, though, continued to anchor the staff, well into his 30s. In 2018, he earned his second All-Star selection with the Cubs, winning 18 games. Unfortunately, because of the pandemic, he never got that final moment with the fans, walking off the mound to a raucous ovation.

Penny-pinching by the organization ultimately ended his time with Chicago, given he said he would have stayed there for ‘just about anything’ prior to heading to Washington last offseason.

Still, Cubs faithful welcomed him back with open arms as a member of the Nationals and the Cardinals in 2021 – and there’s a decent chance that we’ll see Lester around the Confines or the team’s spring training facility in Arizona in years to come. Whether it all ends in Cooperstown or not, Lester had one heckuva run as one of the best big game pitchers in baseball history.