14 Cubs players who won't return in 2027 as Jed Hoyer searches for answer to Brewers problem

The Chicago Cubs' season has once again come to a close with the realization that while they made the playoffs, they weren't quite a World Series contender. Perhaps that would have been different if the Cubs had Ben Brown, Justin Steele, and Cade Horton available during the playoffs, but the overall point remains: a gap remains between where they are and where the Milwaukee Brewers are.

If we're being honest, even the Wild Card series proved that a gap may exist between the Cubs and San Diego Padres.

As Cubs flip the page from the playoffs to the offseason, one of the first orders of business for Jed Hoyer is determining the players that won't be back with the team in 2027. Sure, most of this is settled by free agency, but there are a number of trade candidates. With there potentially being a work stoppage on December 1, there's no time to waste.

Here's every Cubs player who shouldn't be back with the team in 2027.

Matthew Boyd

Every member of the Cubs' current starting rotation is set to become a free agent upon the conclusion of the World Series. While the Cubs could have interest in retaining some arms, the guess here is that they don't retain Matthew Boyd. He's certainly done his part over the last two years, but with how the Cubs operate, it's hard to imagine they are willing to sit at the top of his market, considering the regression that peaked through this season.

Kevin Gausman

When the Cubs first traded for Kevin Gausman at the trade deadline, the impression was that he could be a candidate to re-sign with the Cubs during the offseason. That's still the case, but given the up-and-down nature of his run in Chicago, the Cubs probably won't race to sign him to a new contract.

Hunter Harvey

Harvey was a waste of $6 million for the Cubs this season. He made four appearances before being lost for the entire season due to a triceps injury. There's no scenario where the Cubs entertain the idea of bringing him back.

Shota Imanaga

Shota Imanaga was tough to figure out this season. He had stretches where he pitched like the clear ace of the rotation, and stretches where Craig Counsell had to use a short leash for his starts. The Cubs weren't eager to keep Imanaga around long-term last offseason, and chances are they haven't really shifted from that idea.

Colin Rea

Despite being a savior for the Cubs' pitching staff over the last two years, the Cubs relegated Colin Rea to mop-up duty by the end of the 2026 season. That's pretty telling of the lack of future he has in Chicago.

Caleb Thielbar

Towards the end of the 2026 season, Caleb Thielbar was closer to being a DFA candidate than he was to Craig Counsell's circle of trust. He was brought back by the Cubs last offseason, but chances are there's no offseason reunion this time around.

Carson Kelly

Carson Kelly is positioned to be one of the best catchers available on the free-agent market this winter. The Cubs likely would love to have him back, but they likely won't be willing to outspend the competition for his services.

Gabriel Arias

A fine late-season addition to the bench while the Cubs were without Dansby Swanson, but there's no reason to bring him back as a bench option for the 2027 season.

Tyler Austin

A knee injury during spring training prevented Tyler Austin from making his return to the majors, and it feels foolish for the Cubs to spend actual money again on the hope that he could be a contributor moving forward.

Ian Happ

With both Seiya Suzuki and Ian Happ free agents this winter, the Cubs will need to shuffle some parts around in the outfield. The guess is the Cubs prefer to bring back Suzuki and are comfortable letting Happ walk via free agency.

Matt Shaw

The Cubs will have a need for pitching this offseason, and they likely will be focusing on the trade market. If that's the case, Matt Shaw will be a trade chip in talks for controllable starting pitcher.

Tyrone Taylor

There's a case to be made that the Cubs should look for a way to bring Tyrone Taylor back for the 2027 season. The problem is this year's free-agent class is weak, and Taylor likely will get a healthy deal, consider how he's looked with the Mets and Cubs this season.

Kevin Alcantara

Kevin Alcantara is out of minor-league options and it's never felt like the Cubs have been eager to keep him around. The guess here is that he's traded as a change-of-scenery candidate during the offseason.

Michael Conforto

The Cubs will thank Michael Conforto for his efforts in 2026, but given the number of position players that are reaching the top of their farm system, there's no need to make Conforto's return a priority.

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