Chicago Cubs News: Looking at key Cubs who will be free agents

Theo Epstein - Mandatory Credit: Rick Scuteri-USA TODAY Sports
Theo Epstein - Mandatory Credit: Rick Scuteri-USA TODAY Sports /
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(Photo by Jonathan Daniel/Getty Images)
(Photo by Jonathan Daniel/Getty Images) /

Chicago Cubs: Most of the biggest names on the list of upcoming free agents this year are pitchers.

Jon Lester (SP)

We will include Lester on this list. His guaranteed six years as a Cub are up, and 2021 is a club option at $25 million (vesting option requirements were not met). It is expected that the Cubs will buy out his contract at $10 million, and he will become a free agent.

Whether or not the Cubs re-sign him to a smaller deal in 2021 is yet to be seen. It cannot be ruled out, especially if he signs cheap, and they need starter depth. Lester struggled last year with a 5.16 ERA and 1.33 WHIP in 12 starts as Father Time is taking over the former All-Star and postseason hero. Do not be surprised either if he goes back to Boston.

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Jose Quintana (SP)

Cubs fans cringe thinking about Quintana’s tenure as a Cub when they see Eloy Jimenez crushing 450-foot shots for the South Siders. The veteran who came over in the historic blockbuster deal with the White Sox in 2017 was not as consistent as he was on the South Side. He only pitched in four games this year due to some bizarre injuries. If he does come back, it would be on a new cheaper deal and likely not a qualifying offer, which is almost $19 million. While not confident he is not coming back, it seems less likely he will be.

Tyler Chatwood (SP/LRP)

His three-year, $38 million deal has expired after a roller coaster of a ride. The first year in 2018 was horrendous as he walked 95 batters in 103 2/3 innings. 2019 was noticeably better as a long reliever/spot-starter when he put up a 3.76 ERA in 41 games. 2020 he started fantastic as a starter but then got crushed in Kansas City and then got hurt and finished the year only pitching in five games. Guess is he will be pitching elsewhere in 2021.

Jeremy Jeffress (RHP/CL)

After struggling in 2019, the veteran reliever signed a one-year, $850K deal with the Cubs in 2020 to regain form and play for another contender. Jeffress was the team’s most reliable and consistent reliever as he pitched to a 1.54 ERA, 0.943 WHIP, and recorded eight saves in 22 appearances. This feels like a case where he will be seeking a more significant opportunity in 2021 after his bounce-back 2020 season. I would not be surprised if he goes elsewhere next year.

Next. Cubs cannot part with Willson Contreras. dark

There you have it. The list is not extensive outside of pitchers. The names becoming free agents can, for the most part, easily be filled in. It is just a matter of what new talent the Cubs want to bring in and where some of the upcoming prospects will be projected in 2021. So many questions about the future, right now, very few answers.