MLB Rumors: Will 2020 be Jon Lester's last year with the Cubs?

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Is this the last dance for Jon Lester with the Cubs?

The lefty’s contract has a vesting/mutual option for 2021 for a guaranteed $25 million if he pitches 200 innings in 2020 (the number of innings will be prorated based on the actual number of games played this year). Should Lester not reach that number, the Cubs can buy out his deal for $10 million.

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Lester was asked about his future in an interview with Rob Bradford of WEEI.com:

“We’ll figure that out one way or the other. I will either be here or be a free agent. … I’m open-minded to anything.”

“Hopefully, I’m still a good enough caliber pitcher that the want of my services will still be out there for people.  I’m not getting any younger, and coming off a year like I had last year, this [season delay] isn’t going to help me.”

Last year was a rough one for Lester. He saw his ERA jump from 3.32 in 2018 to 4.46 in 2019. The 205 hits allowed (in 171.1 innings) were the most by any National League pitcher.

No matter what numbers he puts up from here on out, his $155 million contract has been one of the best investments the Cubs have ever made.

His signing at the 2014 Winter Meetings kicked the rebuild into high gear. He has started at least 31 games in each of his first five seasons with the club. In his 159 regular season starts, his ERA is 3.54; in 12 postseason appearances, his ERA is 2.44. A solid 2020 season would make him an attractive option for any team in need of a veteran back-of-the-rotation starter.

Could that be with the Cubs? Absolutely, especially with the team’s struggles to develop pitchers and the impending free agency of another starter, Jose Quintana. It could also mean a return to Boston, the organization Lester pitched for from 2006 to 2014.

“Absolutely it would be cool to go back and finish my career where it all started.”

So Lester has options beyond this year. Baseball fans can only hope he will be able to show he still has what it takes to be successful on the mound at some point in 2020.

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