The Major League Baseball winter meetings next week in Orlando, Florida, are shaping up to be eventful, with plenty of action already stirring.
That’s a change from 2023 and 2024, when Shohei Ohtani’s and Juan Soto’s market-setting free agencies put some of the heavyweight teams in a holding pattern leading up to the meetings.
Still, the 2024 meetings were productive for the Cubs after they already had signed left-hander Matthew Boyd in the days leading up to them. They laid the groundwork to acquire outfielder Kyle Tucker from the Astros and to sign catcher Carson Kelly, although the moves were finalized after the teams departed Dallas.
This year, top free-agent pitchers already have found landing spots. The Blue Jays, who are making an aggressive push after winning the American League pennant, signed right-hander Dylan Cease to a seven-year deal worth $210 million, the largest free-agent contract in franchise history.
From the top tier of the free-agent group of relievers, Devin Williams (Mets, three years, $45 million), Ryan Helsley (Orioles, two years, $28 million) and Raisel Iglesias (Braves, one year, $16 million) already had agreed to contracts for 2026 and beyond a week before the meetings.
Not to mention that the Mets and Rangers pulled off a stunning trade, swapping outfielder Brandon Nimmo and second baseman Marcus Semien; the Orioles acquired outfielder Tyler Ward from the Angels for promising young pitcher Grayson Rodriguez; and the Red Sox acquired veteran right-hander Sonny Gray from the Cardinals. All this before Thanksgiving.
Put baseball executives and agents under the same roof for a few days, and the action is bound to ratchet up.
The Cubs’ most notable moves so far have been signing reliever Phil Maton to a two-year contract worth $14.5 million and bringing back left-hander Shota Imanaga on a $22.025 million qualifying offer for 2026.
Pitching remains at the top of the Cubs’ list entering the meetings, but president of baseball operations Jed Hoyer also hopes to improve the bench from this past season, when it was a soft spot.
Bullpen
The Cubs already have begun the massive construction project of filling out their bullpen. Maton’s two-year deal was the first multiyear contract they had given to a reliever since Craig Kimbrel in 2019.
By sheer numbers, it’s clear a majority of the Cubs’ moves this offseason will involve relievers. But how much more financial capital are they willing to dedicate to that group?
Coming out of the general managers meetings last month, speculation spiked that the Cubs would pursue right-hander Pete Fairbanks. According to a league source, however, they never made a serious push to sign the former Rays closer.
That doesn’t necessarily preclude the Cubs from pursuing relievers in a similar tier, but a majority of their reliever signings are expected to be short-term commitments, including minor-league deals.
Starting pitching
Even though Cease is off the board, there are plenty of free-agent starters still available, with Framber Valdez, Ranger Suarez and Tatsuya Imai among those with clear frontline potential.
Hoyer has been careful not to divulge the Cubs’ offseason budget, so it’s unclear whether the top tier of free-agent pitchers will end up out of their reach.
The Cubs have an organizational philosophy against deferrals, which might serve as another self-imposed impediment. The Blue Jays, for instance, reportedly used deferred money to bring Cease’s $210 million contract down to a more manageable present-day value of about $184.6 million, as calculated by the players’ union.
Conversations from the trade deadline are sure to carry over into the offseason, too, after marquee starters with multiple years of team control stayed put. Starters such as the Twins’ Joe Ryan, the Marlins’ Edward Cabrera and the Nationals’ Mackenzie Gore might be available via trade.
It’s yet to be seen whether conversations about those pitchers will progress further than they did at midseason.
Bench
The buzz around the Cubs during the meetings mostly will be about pitching, but they also are looking to put together an improved bench this offseason. That eventually will mean major-league deals.
On Tuesday, however, the Cubs added potential Triple-A depth to that mix. They announced they had signed utility player Scott Kingery to a minor-league contract with an invitation to major-league spring training.
Kingery’s best season was 2019, when he hit .258 with 19 home runs for the Phillies, but he has played sparingly since. He returned to the majors for the first time in three years when he played in 19 games for the Angels in 2025.