Potentially 18 current Chicago Cubs players could become free agents heading into 2027. From that group, some choices are obvious, a few more the team should 100% explore reuniting with, and some that have absolutely no business returning next year. Then there are the players who fall into a gray area: the Cubs are on the verge of losing tons of talent, but some things have to change after another disappointing end in 2026.
I’ll put these at close to 50/50 in terms of having a legitimate interest. However, as we’ve seen with Jed Hoyer’s history, he hasn’t operated recklessly in free agency. So, even if you disagree with a reunion for any of these players, no deal should hurt the organization’s goal of upgrading overall for 2027 and beyond.
5th Starter
Matthew Boyd: $15 million mutual option, $2 million buyout
Kevin Gausman: Unrestricted free agent
Shōta Imanaga: Unrestricted free agent
David Peterson: Unrestricted free agent
Again, the key is that if the Cubs pursue any of these four starting pitchers, they’d only do so with the intention of making a much bigger move to upgrade the rotation. You’d only want one back from this group, and although they have each had their own stretch of success in 2026, the least familiar name might be the most tantalizing to re-sign, and that’s David Peterson
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First off, Peterson, 31, is the youngest of the four pending free-agent starting pitchers, and the left-hander has the perfect mix to pitch behind the Cubs’ elite defense. In 80.1 innings with the Cubs this year, Peterson posted a 3.70 ERA and a 49.1% ground-ball rate.
Matthew Boyd was good for what he was, but as he enters his age-36 season, you start to worry about his decline, and the upside just isn’t as high anymore. Shōta Imanaga had a solid end to the regular season, but if you can’t be trusted to start in the playoffs for two straight years because of the home run concerns, then more likely than not the Cubs are ready to move. Speaking of moving on, it seems Kevin Gausman may already have his mind made up as he enters free agency, and while it is a reunion, it doesn’t appear to be with the Cubs.
Peterson would be a solid fifth starter for the Cubs in 2027, and after being an All-Star in 2025, he still has the ability to perform at a higher level.
Carson Kelly ($7.5 million mutual option, $1.5 million buyout)
This one is tough because the Cubs would obviously love to re-sign Carson Kelly after two stellar years on the North Side of Chicago, but will they pay to keep him? He’ll decline the mutual option for the 2027 season, and since the Cubs aren’t willing to engage in a bidding war for one of their best hitters, Seiya Suzuki, how motivated will the front office be to invest in a veteran catcher?
Miguel Amaya is a suitable backup behind the plate, and the organization hopes that catching prospect Owen Ayers can contribute in 2027 after his ascent through the Cubs’ farm system this season. Still, it would be tough to move on from a steady player like Kelly, who has been that way for the past two years. It’ll come down to his contract demands, and a somewhat crowded catcher market could potentially bring his market back to a comfortable area for the Cubs.
However, this one still seems unlikely, even though the Cubs probably want to keep Kelly around if their offseason budget wasn’t mostly focused on pitching.
Aaron Civale (Unrestricted Free Agent)
This will need some convincing, because Aaron Civale has publicly stated in the past that he 100% prefers to be a starting pitcher. However, in two separate stints with the Cubs, the right-hander has thrived out of the bullpen. Civale’s 2026 performance was especially great, as he posted a 1.72 ERA in 36.2 innings with the Cubs.
Opposing hitters averaged only an 82.9 mph exit velocity against Civale, who did a superb job limiting hard contact. He may be redundant in the bullpen, since we assume Colin Rea will be back, but if Civale buys in, he could become a trusted bullpen arm moving forward.
In the past two years, Civale has posted a 2.42 ERA with a 51-to-13 strikeout-to-walk ratio in 52 innings as a reliever. Bring him back, but only if he’s willing to become a full-time reliever.
Ian Happ (Unrestricted free agent)
This one is pretty simple, and we’ve discussed it before: just how much of a hometown discount is Ian Happ willing to take to stay with the Cubs? The left fielder has almost begged in the media to return, but that won’t happen unless Happ takes a huge pay cut after his three-year, $61 million contract extension expires.
The Cubs were already taking plate appearances away from Happ after the trade deadline, sitting him against left-handed pitching, so they now view him as a platoon bat and not an every-day player. Again, reports in early October indicate that the Cubs will use most of their money on pitching, so that doesn’t bode well for Happ.
However, if Happ really does take a big pay cut, the Cubs would definitely be interested in signing him to a short-term deal.
