The Cubs are staring down a messy winter, and the free-agent class headed into 2027 makes that clear. A handful of familiar names could be on the board, but not every reunion makes sense.
Some moves would be easy. Some should be explored.
And some, frankly, would make no sense at all.
The trickier cases sit in the middle. Chicago is set to lose a lot of talent, but after another disappointing finish in 2026, the front office can’t just run it back and hope for better. Jed Hoyer also hasn’t shown a habit of getting reckless in free agency, so even the players who land in that gray area shouldn’t threaten the larger goal of improving the roster for 2027 and beyond.
If the Cubs bring back one of the four starting pitchers in this group, it would almost certainly be as part of a bigger push to reshape the rotation. They only need one, and David Peterson stands out as the most appealing option.
The left-hander is 31, the youngest of the bunch, and his profile fits behind Chicago’s elite defense. In 80.1 innings with the Cubs this year, Peterson put up a 3.70 ERA and a 49.1% ground-ball rate.
He was also an All-Star in 2025, which leaves enough evidence that there’s still a higher level there.
Matthew Boyd did solid work for what he was, but age is now part of the equation as he heads into his age-36 season, and the upside isn’t what it used to be. Shōta Imanaga finished the regular season well, yet two straight playoff runs without trust to start because of the home run issues points in a pretty clear direction. Kevin Gausman, meanwhile, may already have his own mind made up as he reaches free agency, and if there’s a reunion coming there, it doesn’t look like it’s with the Cubs.
Carson Kelly is another complicated call. Chicago would love to keep him after two strong seasons on the North Side, but the price is the real question.
He’ll decline his $7.5 million mutual option for 2027 and take the $1.5 million buyout, and the Cubs are not expected to get into a bidding war for one of their better hitters, Seiya Suzuki, let alone a veteran catcher. Miguel Amaya is a workable backup, and the organization is hoping catching prospect Owen Ayers can help in 2027 after climbing through the farm system this season.
Kelly has been steady for two years, and that makes this one tough to walk away from, but it still feels unlikely. If there’s a path back, it probably depends on his asking price and a crowded catcher market bringing things back to earth.
Aaron Civale makes for an interesting bullpen case, even if it comes with a clear condition. He has said in the past that he 100% prefers starting, but in two separate stretches with the Cubs, he’s been effective as a reliever.
His 2026 numbers were excellent: a 1.72 ERA in 36.2 innings with Chicago. Opponents managed only an 82.9 mph average exit velocity against him, a strong sign of how well he controlled contact.
He may overlap with Colin Rea if Rea returns, but Civale has been too effective to dismiss. Over the last two seasons, he has a 2.42 ERA with a 51-to-13 strikeout-to-walk ratio in 52 relief innings.
The fit is there if he accepts a full-time bullpen role.
Ian Happ is the clearest name in the bunch, and the issue is money. The left fielder has made it obvious in public that he wants to stay, but that only happens if he takes a major hometown discount after his three-year, $61 million extension runs out.
The Cubs were already trimming his plate appearances after the trade deadline, sitting him against left-handed pitching, which signals they now see him more as a platoon bat than an everyday player. With reports in early October pointing to Chicago spending most of its money on pitching, the outlook gets even tougher.
Still, if Happ is willing to take a significant pay cut, the Cubs would have interest in a short-term deal.
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For a few of the young names who matter now, that kind of planning creates pressure as well as opportunity. Matt Shaw, Pedro Ramirez, Kevin Alcantara and Jordan Wicks are among the players viewed as possible trade candidates if Chicago decides it needs to reshape the group around a different core, which means every step they take from here matters a little more. The Cubs do not need to decide everything today, but the list of youngsters who can safely assume they are part of the long-term picture is not very long. [Read more 🡒]
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Cubs Facing Some Uncomfortable 2027 Bullpen Decisions Already
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Thielbar has slipped from the kind of reliable late-inning arm the Cubs hoped for, Harveys value was undercut by another injury-hit season in 2026, Thorntons run prevention has not come with the strikeout punch teams want from a bullpen piece, and Austin has not offered much since his surgery. Put together, it leaves Chicago with an uncomfortable but familiar front-office task: deciding which relievers are worth another chance and which ones are better left off the 2027 plan. [Read more 🡒]