Every Cubs Player Who Might Not Be Back in 2027 After Wild Card Disappointment

These Cubs players may have just played their final game in a Cubs uniform as a big free agency period awaits.

Sep 30, 2026; San Diego, California, USA; Chicago Cubs outfielder Seiya Suzuki (27) looks on during batting practice prior game two of the Wildcard round for the 2026 MLB Playoffs against the San Diego Padres at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images | IMAGN IMAGES via Reuters Connect

With the Chicago Cubs' 2026 season coming to an ugly end on Wednesday night, the offseason has begun for President of Baseball Operations Jed Hoyer and his front office.

With 16 pending free agents worth nearly $150 million, the Cubs will not only have some money coming off their books, but they'll have plenty of roster holes that need to be filled. Almost the Cubs' entire starting rotation in Shota Imanaga, Matthew Boyd, Kevin Gausman, Clay Holmes, David Peterson, and Colin Rea could be headed out the door.

The only starters from this season signed for next season are Edward Cabrera, Ben Brown, and Cade Horton, who likely won't be healthy until late June or July of 2027. The Cubs will also see two of their best outfield bats hit the open market, and they're bound to have serious competition to retain them.

With that in mind, let's run through who's staying and who's going now that the Cubs have had the book closed on 2026.

The Pitching Staff will look a lot different in 2027

Sep 27, 2026; St. Petersburg, Florida, USA; Chicago Cubs pitcher Shota Imanaga (18) delivers a pitch during the first inning against Boston Red Sox at Tropicana Field. Mandatory Credit: Pablo Robles-Imagn Images | IMAGN IMAGES via Reuters Connect

Unrestricted Free Agents: Shota Imanaga, Kevin Gausman, David Peterson, Aaron Civale

Mutual Options: Matthew Boyd ($15 mil), Hunter Harvey ($8 mil), Caleb Thielbar ($6 mil)

Player/Club Options: Clay Holmes ($12 mil player option), Colin Rea ($7 mil club option), Jacob Webb ($2.5 mil club option)

I think there's a good chance the Cubs could bring back David Peterson. He pitched well for them and could slide between the rotation and bullpen. Clay Holmes seems unlikely to accept his $12 million player option but was reportedly open to an extension with the Mets in July. I'd love to see him back with the Cubs, but I do expect him to test free agency.

Matthew Boyd seems like a player the Cubs wouldn't mind keeping for the back end of the rotation with upside. A 2-year deal around $30 million feels reasonable. But the remaining names may very well be leaving the team, including fan-favorite Shota Imanaga, who surprisingly accepted the Cubs' qualifying offer last winter. Justin Steele's return to the rotation could also mean both Boyd and Imanaga are gone, as well.

If the market isn't great for Kevin Gausman, perhaps the Cubs will look to retain him after Jed Hoyer apparently tried to acquire him a few times over the years. Colin Rea would make sense as a returning player, too. However, considering he has a $7 million club option, it might depend on how much money they've already spent in the offseason.

The Cubs Could Lose Multiple Important Bats

Sep 30, 2026; San Diego, California, USA; Chicago Cubs outfielder Seiya Suzuki (27) reacts after a single in the fourth inning against the San Diego Padres during game two of the Wildcard round for the 2026 MLB Playoffs at Petco Park. Mandatory Credit: Denis Poroy-Imagn Images | IMAGN IMAGES via Reuters Connect

Unrestricted Free Agents: Ian Happ, Seiya Suzuki, Tyrone Taylor, Michael Conforto, Tyler Austin

Mutual Options: Carson Kelly ($7.5 mil)

Ian Happ has potentially played his last game as a Chicago Cub, which is sad because he's the longest-tenured Cubs and Chicago athlete. But as valuable as he's been for the Cubs as a gold-glove left fielder, it's just not a necessity. And with the Cubs expected to allocate most of their resources to pitching, it could mean Happ becomes a casualty.

Seiya Suzuki absolutely should be a priority for the Cubs this offseason, but in a weak free agency class, he could get an offer the Cubs may have to pass on. I hope that isn't the case, but I could easily see a team like the Dodgers price the Cubs out of Suzuki's market.

Carson Kelly could return, and his $7.5 mil mutual option is reasonable. However, I don't expect any of Tyrone Taylor, Michael Conforto, or the injured Tyler Austin to return next season. If Conforto or Taylor are open to a bench role, or the Cubs find a good platoon partner for either, I guess that could work, as well.

The Cubs' focus will be adding arms to a rotation that once again crumbled on their way to the playoffs. But the offense will need to be addressed this offseason after scoring just one run in the Wild Card series.

It's going to be a long offseason filled with labor discussions and threats of a potential lockout that cloud the future of the Cubs and Major League Baseball.

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