We’ve talked a lot about Kyle Tucker’s free agency here over the last few days.
The Cubs have eight other players who will officially be free agents after the World Series is over, plus four other players with various types of options. So let’s have a look at all of them and discuss whether the Cubs should try to retain them or not. Interestingly, all but two of the 12 players are pitchers.
First, the players with contract options.
Shōta Imanaga
Imanaga’s contract situation was discussed in After Dark a few days
ago, and his contract setup is complex, with multiple player and team choices.
Despite Imanaga’s struggles, I think the Cubs should keep him. It’s possible that the hamstring injury that forced him to miss several weeks in May and June was still bothering him much of the year and contributing to his rough second half.
Honestly, I’m not sure which road the team should take, picking up the team options or letting Imanaga have his player options. But I do believe he should be a Cub on Opening Day 2026.
Andrew Kittredge
Kittredge has a $9 million team option for 2026. I’m on the fence here. The Cubs should probably pay Brad Keller to stick around, and $9 million is probably around what that’s going to cost. Do they want to pay two similar guys that much?
Colin Rea
Rea has a $6 million team option for 2026. Pay the man.
Justin Turner
Turner has a $10 million mutual option or a $2 million buyout.
Seriously, if Jed Hoyer picks up the mutual option that’s executive malpractice. Thank the man and give him his $2 million.
Now, the 2025 Cubs who are unrestricted free agents (other than Tucker).
Ryan Brasier
Brasier threw well, at times. And didn’t, at others, and finished the year on the IL. He’s 38 and the Cubs picked him up from the scrap heap. They can probably find someone better on that heap for 2026.
Aaron Civale
Civale threw well for the Cubs after not doing so as a starter for the Brewers and White Sox. Could the Cubs turn him into a reliever similar to Keller? Worth looking into, anyway.
Brad Keller
He was a revelation, a failed starter turning into a 98 mile per hour leverage reliever. He just turned 30 in July and could be productive for several years. The Cubs should explore a multi-year deal.
Drew Pomeranz
Pomeranz resurrected his career after not pitching in the major leagues for four years. He was effective nearly all of the time, and as a lefty, the Cubs could use him again in 2026. He has history with Craig Counsell (pitched for him in Milwaukee in 2019) and won’t be expensive. The Cubs should look to retain him.
Taylor Rogers
See ya.
Carlos Santana
It won’t be long before people say, “That guy played for the Cubs?” (If they’re not doing so already).
Santana had a very good MLB career that included 335 home runs. Exactly zero of those were for the Cubs, for whom he went 2-for-19.
Thanks for the, uh, memories, Carlos. He’s a good Immaculate Grid answer, anyway.
Michael Soroka
Soroka has talent, he was a first-round pick of the Braves in 2015.
But he is always injured. Like, really, always. He pitched reasonably well in a handful of outings for the Cubs and is still only 28. Maybe the Cubs could turn him into a Keller-type leverage reliever. I wouldn’t spend too much money on that, though.
Caleb Thielbar
Here is a place where I would dismiss age — Thielbar turns 39 in January — and say that the Cubs should try to bring him back, at a reasonable price. Thielbar made $2.75 million in 2025 and a similar deal for 2026 might be worth it.
