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

Many Chicago Cubs will become free agents next year. Who do you think will get a contract for next season?

Let’s face it; the Chicago Cubs will be full of free agents in 2021. And to be honest, the clock is ticking on them in regards to signing them. So, who’s it going to be? There are a few names in there who could be a viable resource.

But it’s going to be signing them that’ll be not easy. A pitcher that has a $25 million club option and hasn’t been worth that much. Or a pitcher has an $850K deal, but that has to be added to it because he has been huge this season. Maybe an outfielder who plays all three spots? All three, or nothing at all? That is the question.

We have all that and then some as far as players who the Cubs should be on the lookout for. Theo Epstein and his rebuild will not play this year. But he should be done by 2021, and the Cubs will find a new President of Baseball Operations. Epstein has a ’10 year plan’ in place, and he’s going to keep it.

Editors Note: I picked a handful of club options or free agents, to be fair

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?

Chicago Cubs’ Jeremy Jeffress

The Cubs’ Jeremy Jeffress. The $850K pitcher. That would go up after the season he had. Look, I’ll be honest. Jeffress did not have a good year for the Milwaukee Brewers. He had an array of injuries, and that slowed him down. So he took a deal with the Cubs and that paid dividends for him.

In 2019 with the Brewers, he was rubbish. He posted a 5.02 ERA in 52 innings of work. So onto the Cubs, South down I-94. The results– 1.54 ERA, 23 1/3 innings, one home run and an ERA+ of 292. He appeared in about a third of them, striking out 17. That’s a run and a half different–but that’s pitching to contact.

I don’t know what’s going to happen with Jeffress. He’s ‘on the fence’ as far as where he stands. He could come this way and sign a one-year deal–for more than $850K, though. Or he can hold court over free agency and see where it takes him.