Complete list of Cubs free agents with final predictions for who stays and who leaves in 2027

Before we know it, the offeseason will be here and, even with the uncertainty brought on by the expiring CBA and a potential lockout, front offices will have work to do. Jed Hoyer and the Chicago Cubs face a lengthy list of likely departures via free agency, including some long-standing members of the organization.

So let's go through the full list of Cubs free agents, one-by-one, and we'll give you predictions on whether they're back on a new deal or move on to a new home come Opening Day 2027.

Predicting which Cubs free agents stay and which will have new teams

Kevin Gausman

One of the Cubs' big trade deadline acquisitions has been all over the place down the stretch, looking like the front-of-the-rotation piece Hoyer hoped he was acquiring at times and, at others, running into big blow-ups on the mound (5.04 ERA in eight starts). Set to turn 36 in January, the veteran right-hander will probably get a one or two-year deal somewhere, but it won't be with Chicago.

Prediction: Departs in free agency

Shota Imanaga

After a complicated back-and-forth last winter thanks to a complicated contract structure, Shota Imanaga and the Cubs came back together via a qualifying offer. He's largely rewarded that faith, working to a 3.74 ERA across a 173 1/3 innings, which ties a career-high. The long-ball remains an issue (34 home runs allowed leads the league) and it feels like he'll be pitching somewhere else in 2027.

Prediction: Departs in free agency

Ian Happ

It's really unfortunate that what may be Ian Happ's final season with the Chicago Cubs has been so underwhelming. A career-low batting average driven almost entirely by his struggles from the right-handed side of the plate (.148/.221/.273) has forced him into platoon duties in the second half. As the longest-tenured player on the roster, I think a soft market could lead to a team-friendly reunion this offseason.

Prediction: Re-signs with the Cubs in free agency

Seiya Suzuki

Seiya Suzuki is one of the most underrated and underappreciated players in baseball. He's proven to be a consistent run-producer during his five years on the North Side and he's set himself up for a major payday in free agency. Sitting around 5.0 bWAR with proven 30-homer, 100-RBI production at the plate, Suzuki is poised to cash in this winter.

Prediction: Departs in free agency

David Peterson

Picked up out of sheer desperation in June, David Peterson helped keep the Cubs' rotation afloat as it battled injuries and ineffectiveness. Chicago faces a ton of change on the pitching front, but the left-hander fits perfectly with how the team is constructed. He gives you a chance to win just about every time out and I think Hoyer looks to keep him around this offseason.

Prediction: Re-signs with the Cubs in free agency

Aaron Civale

I mean, if I'm Aaron Civale, I want to come back to the Cubs because, for whatever reason, he's pitched better here than anywhere else over the last two years. With the Cubs, he has a sub-2.00 ERA and, with the Athletics, White Sox and Brewers, that number jumps to north of 5.00. But given the starting pitching market, I think he gets a deal and a shot to return to the rotation in 2027.

Prediction: Departs in free agency

Tyrone Taylor

Clay Holmes was obviously the centerpiece of the Cubs' trade deadline deal with the New York Mets, but Tyrone Taylor has been a key contributor for Craig Counsell since then. Similar to how he's set up Michael Conforto for success, allowing for a bounceback campaign, the Cubs' skipper has followed suit with Taylor - and the results speak for themselves (.343/.387/.493 w/ Chicago). That being said, the two sides will part ways this winter as he looks for his next opportunity.

Prediction: Departs in free agency

Michael Conforto

Similar story here with Michael Conforto. After a brutal 2026 with the Los Angeles Dodgers (that did, at least, get him a World Series ring), the veteran outfielder has looked like his old self this year with the Cubs, with an OPS north of .800 in 300+ plate appearances. That should be enough to set him up in free agency with both sides looking back appreciatively at what he did this season.

Prediction: Departs in free agency

Tyler Austin

Remember when the Cubs signed Tyler Austin to be a backup to Michael Busch at first and add some pop off the bench? I wouldn't blame you if you don't because we never saw him in game action due to a knee injury. It was just a $1.5 million deal but given he just missed the entire season and is in his mid-30s, I don't see Hoyer running it back and hoping for a different result.

Prediction: Departs in free agency

Breaking down the full Cubs list of team, player and mutual options

Clay Holmes

The starting pitching market is light behind Tarik Skubal, so re-signing Clay Holmes will be a tough task for the Cubs' front office - but it's one Hoyer is up to. The right-hander thrives by keeping the ball on the ground and letting the defense work. Holmes will decline his $12M player option, but Chicago brings him back on a multi-year deal to anchor the rotation.

Prediction: Re-signs with the Cubs in free agency

Matthew Boyd

I love Matthew Boyd. Seriously, might be the most genuinely good human being in the game today. He gets what it means to be a Cub and has pitched some big games in his two years with Chicago. Mutual options are alost never picked up and I suspect that's the case here as he parlays his strong run with the Cubs into a new deal on the open market as he heads into the back half of his 30s.

Prediction: Departs in free agency

Colin Rea

If you look up 'Colin Rea' in the thesaurus, 'unsung hero' comes up. I know the numbers could be better, but the big right-hander was so important to the team in 2025, filling in for Justin Steele in the rotation. He's played the swingman role well again this year, albeit to less effective results. This feels like the time to thank him for what he's done and part ways, rather than pick up the $7.5 million team option.

Prediction: Departs in free agency

Hunter Harvey

The biggest free-agent bust of the Cubs' offseason, Hunter Harvey was a total non-factor for the team. Hoyer inexplicably handed him a $6 million deal, only to watch his season draw to a close after only four appearances. Yes, the stuff is there, but as we've learned multiple times over, that can't overrule health questions. Good luck wherever you land, Hunter, because there's zero chance the Cubs are picking up their end of an $8 million mutual option.

Prediction: Departs in free agency

Carson Kelly

I think the Chicago Cubs are going to miss Carson Kelly a lot when he's playing elsewhere in 2027. He's handled everything that's come his way with the pitching staff (seriously, think about how many arms he's had to learn this year alone) without missing a beat at the plate and has been everything the Cubs hoped for when they signed him. He'll decline his end of the mutual option and go get paid on the open market in a dismal catching market.

Prediction: Departs in free agency

Caleb Thielbar

The Caleb Thielbar reunion tour hasn't gone nearly as well as the first iteration and I don't think anyone expects the veteran lefty back in Chicago next year. He turns 40 in January and has an ERA in the 5.00 range. This one is clear-cut: mutual option is declined and, frankly, it may be the end of his 10-year MLB career.

Prediction: Departs in free agency

Jacob Webb

He's fallen on hard times when the team has needed him most, but big-picture, Jacob Webb has been good far more than bad this year. The Cubs will pick up his $2.5 million option for 2027, but hopefully build out the bullpen around him and let him be a seventh or eighth-inning weapon next season.

Prediction: Returns to Cubs on player option

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