The Chicago Cubs, as expected, will experience some significant turnover ahead of the 2026 season.
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In terms of position players, there’s the hole Kyle Tucker will leave in right field if/when he leaves the team via free agency. The Cubs will also have to fortify the bench as Justin Turner and Willi Castro move on.
On the pitching side of things, there will be a lot of work to do. A complete rebuild of the bullpen will have to be done. Of the bullpen arms on the NLDS roster, only Daniel Palencia and Ben Brown are guaranteed to be Cubs this coming season. There’s also some work to be done in the starting rotation as Shota Imanaga may soon be an ex-Cub and the returning Justin Steele may not make his presence felt until mid-season.
The front office has publicly declared that their focus will be on pitching this winter, but there have been conflicting reports as to how much they’re willing to spend to acquire top level talent.
With all of that in mind, Chicago has to first attend to in-house matters before bringing in new blood. Here’s a brief update on the team’s five most crucial free agents and how likely they may be to remain a Cub.
Kyle Tucker: Pretty much gone
Mar 29, 2025; Phoenix, Arizona, USA; Chicago Cubs outfielder Kyle Tucker (30) hits a two-run home run against the Arizona Diamondbacks in the fifth inning at Chase Field. Mandatory Credit: Rick Scuteri-Imagn Images
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At this point, the Cubs are all but acknowledging the fact that the four-time All-Star will be gone. With execs talking up a focus on pitching and their desire to let young players Owen Cassie and Moises Ballesteros get playing time, they’ve all but declared themselves to be out of the Tucker bidding war before the first shot is even fired.
The 28-year-old Tucker will be the most sought-after position player in this free agent class and is expected to nab a contract in the neighborhood of $400 million for 10-11 years. The Dodgers have been mentioned as favorites to sign him, but the Blue Jays have recently emerged as top suitors, joining the Yankees, Giants, and Phillies.
Shota Imanaga: Uncertainty reigns supreme
Sep 19, 2025; Cincinnati, Ohio, USA; Chicago Cubs starting pitcher Shota Imanaga (18) pitches against the Cincinnati Reds in the first inning at Great American Ball Park. Mandatory Credit: Katie Stratman-Imagn Images
The Cubs bailed on their Imanaga option, which would’ve added three more years to his deal at a total of $57 million. Imanaga, in turn, declined his two-year, $30 million player option. The Japanese lefty is now a free agent, but the Cubs’ subsequent $22 million qualifying offer has complicated things.
There’s a distinct possibility that the 32-year-old will take the qualifying offer and count on a healthy rebound year in order to hit free agency in a better position next season. But, then again, he could just walk and sign on to a better deal if one comes his way when testing the market. There’s also the possibility that he comes back to Chicago and rejoins the team on a reconstructed contract.
Imanaga’s future with the Cubs is still very much TBD.
Brad Keller’s big rebound
Oct 8, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Brad Keller (40) celebrates after defeating the Milwaukee Brewers in game three of the NLDS round for the 2025 MLB playoffs at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
Brad Keller walked into spring training as a non-roster invitee, championed by manager Craig Counsell. He finished the season as, arguably, the most reliable pitcher in the Cubs’ bullpen with a 2.07 ERA in 68 appearances and 69.2 innings.
Early projected contract estimates had the 30-year-old going for $15 million over two years, which would’ve been a very doable deal for the Cubs. Rumors of a possible return to the starting rotation, however, have driven up his estimated asking price to $36 million over three years, per MLB Trade Rumors.
The Cubs will be out of the Keller free agent picture if he’s asking starter money.
Drew Pomeranz talk has been nonexistent
MLB: Colorado Rockies at Chicago Cubs May 26, 2025; Chicago, Illinois, USA; Chicago Cubs relief pitcher Drew Pomeranz (45) pitches during the eighth inning against the Chicago Cubs at Wrigley Field. Mandatory Credit: Patrick Gorski-Imagn Images
At this time last year, the lefty Pomeranz was contemplating life outside of baseball. He hadn’t pitched in the majors since 2021 and had languished in the Padres’, Dodgers’, and Mariners’ farm systems. Seattle traded him to the Cubs for cash considerations in April, for what was likely his last shot at a significant major league run.
Pomeranz excelled in this last chance opportunity, posting a 2.54 ERA in 49.2 innings over 57 games and becoming an anchor of the Cubs’ bullpen.
There’s been surprisingly little buzz regarding the market for Pomeranz, which is probably good news when it comes to a possible Cubs reunion. Jim Bowden of The Athletic projected his free agent contract at one-year for $5 million.
Michael Soroka owes it to the Cubs?
Aug 4, 2025; Chicago, Illinois, USA; Chicago Cubs pitcher Michael Soroka (41) throws the ball against the Cincinnati Reds during the first inning at Wrigley Field. Mandatory Credit: David Banks-Imagn Images
Fans were ticked off when Michael Soroka turned out to be the Cubs’ biggest acquisition at the trade deadline this last season. They were extra ticked off when the righty went on the IL after just two innings, in his debut with the team.
The swing man would come back with a good September and a good postseason, until he got beat up in his last outing of the NLDS against the Brewers.
With question marks in both the bullpen and starting rotation, having Soroka’s versatility would be a huge asset to the team. It might also be smart for Soroka to come back to the Cubs, a team that specializes in rehabbing pitchers and one which nursed him back to health last season. ESPN is projecting his contract to be two-years at $23 million, which might be too much for the Cubs. But a one-year deal could be doable as he looks to put together a solid, healthy season before putting himself back into the free agent pool. Another semi-facetious way of looking at it is that Soroka kind of owes a do-over to the Cubs after they gave up two Top 30 prospects for a guy who immediately became a non-factor in the team’s playoff drive.
As is always the case, time will tell how all these Cubs free agent situations resolve.
Chicago Cubs: Rumors are not true, Cubs will not be big spenders this winter, per insider sources
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