Cubs News: Who is most likely to get a contract for 2021?

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Chicago Cubs
Jon Lester – Mandatory Credit: Mike Dinovo-USA TODAY Sports /

Chicago Cubs’ Jon Lester

The Cubs’ Jon Lester is an unusual breed. They picked him up in 2015, and he was terrible. Then in 2016, he was breathtaking. He posted a 19-6 record with a 2.44 ERA. In honesty, he was awe-inspiring. He finished 77-44 with the Cubs with a 3.64 ERA. He took the ball every fifth day and got to work.

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He was a ‘gamer.’ If he didn’t have it, he’d make it up. That’s why the $25 million club option is hard. Epstein said he would be on the hook for it in his later years–and he has been. But make no mistake, Lester was money all day long.

So what’s Lester supposed to do? He’s not going to $25 million from the Cubs. That ain’t happening. So what if he declines? Then he’s a ‘free man’ and able to sign for what he wants. Lester says he’d love to retire in Chicago. How much does that mean?