Chicago Cubs: What does future hold for Jon Lester?

Jon Lester can become a free agent but would the Chicago Cubs welcome him back in 2021?

Jon Lester believed in what Theo Epstein was building here in the Windy City when he signed a six-year, $155 million deal with the Chicago Cubs in the 2014 offseason. Lester was 31 years old at the time and had won two World Series Championships with the Boston Red Sox and spent half a season in Oakland as well. I think most assumed he would return to Boston, a place he was comfortable, a place he had success, which shocked many when he picked Chicago.

Now nearly six years later, Lester will arguably go down as the best free-agent signing in Cubs history. Ben Zobrist is that for a position player, and yes, I know Andre Dawson exists. Lester was invaluable in the Cubs World Series run in 2016, pitching in relief in Game 7, after posting a career-best 19-5 record during the regular season.

He led the National League in wins during the 2018 season, earning his fifth All-Star selection in the process. But last year, specifically August, was not kind to him. Before the All-Star break, Lester looked ageless, posting a 3.72 ERA, but struggled in the second half.

In what was likely going to be his final year in Chicago, the coronavirus pandemic has put his future further in question. As part of his contract, Lester has a $25 million team option or $10 million buyout should he elect free agency.

The Cubs have demonstrated that they aren’t afraid to exercise an expensive team option on a veteran pitcher – see Cole Hamels – but Lester will be 37 years old next year. Obviously, he’s not pitching right now, which helps his cause because no extra mileage is being added to his arm.

But with the Cubs set to lose two other starters to free agency, they are likely to retain at least one of them.

Is Lester worth the $25 million?

Lester’s veteran presence on the roster, especially when the Cubs’ top prospects were first called up, cannot be quantified. Every team has that one veteran on the roster that is essentially the glue holding everything together.

If the Cubs let Lester walk in free agency, the oldest player – outside of a free agent signing – will be Yu Darvish. The Cubs paid John Lackey $16 million per year at age 37 and 38, and he was the perfect back end of the rotation guy.

Lester could transition into that role in 2021 for the Cubs with either a young free agent sliding into the number three slot or a prospect doing the same. The Cubs don’t need Lester to be the ace of the staff anymore, nor should they expect him to be.

We all knew the regression would happen at some point. We just had to hope that the Cubs would win during the front-end of his contract, and they did. Lester, as a fourth or fifth starter, is perfect for him at this stage in his career. The $25 million would be a tough pill to swallow, but, again, his presence is so important, especially for a team that has underperformed the last couple of years.

According to Spotrac, the Cubs have $96 million committed to 2021, so giving Lester the team option would not be the worst idea in the world. That said, they will need to pay a couple of their younger players rather soon. However, I’d like to see Lester stick around for another year while the Cubs continue to let some of their young pitching prospects develop.