January 11: Ken Rosenthal of The Athletic reports that $70MM of Bregman’s $175MM contract is deferred. Rosenthal adds that the deal is expected to fall into the $30MM to $31MM range in terms of average annual value after factoring in the deferrals. This is a notable departure for the Ricketts family in recent free agent negotiations.
January 10: With most of Chicago focused on the Cardiac Bears Saturday night, the Cubs attempted to steal a little bit of the spotlight by agreeing to a five-year, $175MM contract with free agent Alex Bregman. In doing so, the Cubs land MLBTR’s fifth-ranked free agent to take over at the hot corner.
Bregman, a client of the Boras Corporation, bests the contract offers he received last offseason. His new contract, the third-largest in Cubs history, includes a full no-trade clause but lacks opt-outs. The deal also includes significant deferred money.
When last offseason’s proposals fell short of Bregman’s expectations, he pivoted to a heavily-deferred three-year, $120MM deal with the Red Sox. The quality of his 2025 season, plus his ineligibility for a qualifying offer this time around, led to this long-term deal.
MLBTR projected a six-year, $160MM contract for Bregman back in November. He ultimately landed a bit shy of that on a five-year term, when accounting for deferrals. It’s still the largest average annual value in Cubs franchise history.
For the Cubs, the addition of Bregman is the biggest splash in an active offseason. The club acquired young starter Edward Cabrera from the Marlins three days ago, adding upside to the rotation at the expense of a top-50 prospect in Owen Caissie. The Cubs have largely rebuilt their bullpen with a quintet of free agent signings: Phil Maton, Hunter Harvey, Caleb Thielbar, Hoby Milner, and Jacob Webb. They also retained swingman Colin Rea and starter Shota Imanaga.
Bregman gives the Cubs a major offensive upgrade without the loss of a draft pick, as he rejected a qualifying offer from the Astros in 2024. His salary brings the team’s projected 2026 payroll to $231MM, a full $25MM over last year’s $206MM figure, according to RosterResource. Meanwhile, their CBT payroll stands around $243MM for 2026, putting the Cubs just shy of the first luxury tax threshold. The Cubs did not exceed the CBT in 2025, so they’ll reside in the lightest tax bracket if they go over in ’26.
Bregman, 31, played in 114 games with Boston this year, making 495 plate appearances. Although he missed a month and a half with a right quad strain, he continued to excel on offense, batting .273/.360/.462 and grading out 25% better than average by wRC+. After posting a career-low 6.9% walk rate in his final year with the Astros, Bregman bumped that up to 10.3% in 2025. He maintained his reputation as a high-contact hitter, with his 14.1% strikeout rate grading out in the 88th percentile. His 90.1 mph average exit velocity and 44.4% hard-hit rate were both career bests. He also continued to perform well defensively, earning 3 Outs Above Average for his work at third base. Overall, Bregman’s 2025 contributions were good for 3.5 fWAR and his third career All-Star nomination.
A lot of that came from his red-hot first two months. At the time of his injury, Bregman had a 156 wRC+ through 226 PA. His production following his return was more uneven. He posted a 128 wRC+ in July, followed by a 108 wRC+ in August and just a 76 wRC+ in September. In the first half, Bregman was 52% better than average by wRC+. In the second half, he was right around average.
Though he wasn’t his usual self in the last two months of the year, Bregman’s lengthy track record still made him one of the top free agents in this year’s class. Since debuting with the Astros in 2016, he has batted .272/.365/.481 with 209 home runs and a 133 wRC+. His first two All-Star appearances came in 2018-19. Bregman averaged 8.1 fWAR and finished in the Top 5 in AL MVP voting in both years, finishing as the runner-up in 2019.
While he hasn’t reached those heights in the years since, Bregman has still been a well-above-average hitter. He has posted a wRC+ between 117 and 137 in every year from 2020-25. Bregman’s defense has also held firm. Since the start of 2020, he has been worth 10 DRS and 17 OAA. He ranks eighth among qualified third basemen in that span by OAA.
That track record, Bregman’s excellent clubhouse reputation, and his still-excellent 2025 drew ample interest in free agency. The Red Sox were clearly keen on a reunion, with recent reports indicating they had made him an “aggressive” offer. Outside of them and the Cubs, his known suitors included the Tigers, Diamondbacks, and Blue Jays (before they signed Kazuma Okamoto). The Tigers and Cubs were interested in Bregman last offseason as well. Detroit reportedly offered him six years and $171.5MM, albeit with significant deferrals. Chicago’s offer was in the four-year, $115MM range. One year later, the Cubs put forth more than $40MM more to lock him up, even when considering the surprising deferred money.
Bregman likely sought a $200MM guarantee during the 2024-25 offseason. He got to $215MM on paper in total, though deferred money on both contracts probably puts him a little short of a true $200MM. Regardless, returning to the market after opting out of a short-term deal is a strategy we’ve seen Boras execute successfully with Bregman, Carlos Rodon, Blake Snell, Matt Chapman, and Pete Alonso in recent years, with Cody Bellinger serving as the next test case.
With Bregman slotting in at third base, the most impacted player on the Cubs’ roster is incumbent third baseman Matt Shaw. As a rookie, Shaw posted a .226/.295/.394 line in 437 plate appearances, good for a 93 wRC+. Factoring in his serviceable defense (-1 DRS), Shaw was worth 1.5 fWAR in 2025. That was acceptable production for the rookie and former top prospect, though there are clear areas for improvement heading into his sophomore season. Shaw’s average exit velocity and hard-hit rate ranked in the third and seventh percentiles, respectively. He also struggled against fastballs, with a -6 run value against sinkers and a -1 value against four-seamers.
Shaw came up through the system as a middle infielder before shifting to third base in earnest in 2024. At present, Dansby Swanson and Nico Hoerner occupy the shortstop and second base spots on the big-league roster. Swanson is under contract through 2029 and won’t be moving off short any time soon. Hoerner has been an above-average hitter and excellent defender in the past four seasons, tallying 17.5 fWAR. Hoerner moved to second base in 2023 in deference to Swanson.
With the 28-year-old Hoerner eligible for free agency after 2026 – with earning power likely to get a boost from his ability to play shortstop – his name has surfaced in trade rumors this winter. The best 2026 Cubs team has Hoerner at second base and Shaw in a utility infield role, but it’s at least conceivable that either player could be dealt this offseason.
For Red Sox fans, the past seven months have provided a painful sequence of events at third base. Rafael Devers was dealt to the Giants in a surprise June blockbuster, and now Bregman has departed as well. According to Peter Abraham of the Boston Globe, the Red Sox “did not come close financially and were not willing to give Bregman a full no-trade clause.”
The Red Sox, the only team yet to have signed a Major League free agent this winter, could turn to Bo Bichette to play second base. Bichette will likely require a long-term deal of his own, however, and chief baseball officer Craig Breslow has yet to sign a free agent for more than Bregman’s three years (which only lasted one).
Jon Heyman of the New York Post first broke news of the signing, with ESPN’s Jeff Passan adding terms and Bob Nightengale of USA Today providing further details. Ken Rosenthal of The Athletic reported that the deal includes deferred money.
O’Hearn, now 32, has been enjoying a late-career breakout over the past three seasons. He played parts of five seasons with the Royals from 2018 to 2022 with just a .219/.293/.390 line to show for it.