The Red Sox, Diamondbacks, Cubs and Tigers are the remaining most speculated landing spots. ESPN’s Buster Olney suggested last week that Boston has an offer on the table. In one column at ESPN this morning, Olney raised the possibility that the Red Sox might be willing to make something similar to the six-year, $171.5 million offer the Tigers reportedly made to Bregman last winter. There’s no clear reporting on what the Red Sox have brought to the table, just to be clear, so the idea that the Red Sox could continue long-term seems to be mostly informed speculation on Olney’s part.
Boston signed Bregman to a three-year contract with opt-outs last winter. They brought the average annual value to $40 million, albeit with significant delays that dropped the actual value closer to $30 million annually. Bregman is no longer tied to a qualifying offer and has had a better season in terms of rate than 2024. He is also entering his age-32 season, so he may have more incentive to land the longest deal and maximum guarantee. The benefit of signing short-term deals with opt-outs diminishes as a player approaches their mid-30s.
ESPN’s Jesse Rogers and Mark Feinsand of MLB.com Elk wrote Tuesday that many within the industry viewed Arizona and Toronto as the biggest threats to a Boston reunion before the Jays added Okamoto. Of course, that would indicate that the Diamondbacks are now the strongest challengers, but most of the talk about the Bregman/Arizona tie-up involves a potential Kettle Marte trade. With D-Backs general manager Mike Hazen implying they could soon take Marte off the market entirely, that could have a trickle-down impact on Bregman.
Arizona could certainly add Marte and Bregman to the roster. The latter would act as the everyday third baseman. The bigger question is whether ownership will sign another nine-figure investment in the field after Marte was extended for $102.5 million last spring. Long-term payroll would be a bigger hurdle than this year’s prospects. Marte agreed to defer $6 million of his $15 million salary through 2026, so trading him would free up only a fraction of the first-year salary Bregman would have available.
Meanwhile, two of last year’s finalists appear to be less involved this time. Detroit has reportedly shied away from making another long-term offer so far. Top shortstop prospect Kevin McGonigle is on the doorstep of the majors. Bregman would be a significant upgrade over the current third base group Colt Keith, Zach McKinstry and potential Javier Baez as soon as McGonigle arrives.
Manager AJ Hinch gave McKinstry a vote of confidence in response to speculation about a third base takeover. “I get asked about third base all the time. I’m like, ‘Our guy made the All-Star team,'” the Detroit skipper told Audacy’s 97.1 The Ticket (h/t to Evan Petzold of The Detroit Free Press).
McKinstry was indeed an All-Star after an excellent first half, but he was a utility player in his career, hitting .213/.278/.378 after the break. It’s hard to believe he’s actually standing in the way of the Tigers signing Bregman, though it’s understandable that Hinch would publicly defend his player. Detroit’s payroll projection of $165 million is already more than $20 million higher than where they opened the 2025 season, which seems like a bigger obstacle to significant free agent signings.
The Cubs proposed a four-year, $115 million contract last winter. This time they are positioned on the periphery of the market. Matt Shaw had an encouraging second half of his rookie season. President of baseball operations Jed Hoyer and GM Carter Hawkins spoke about their confidence in the 24-year-old infielder during the Winter Meetings. It doesn’t seem like much has changed on that front in the past month. Feinsand reports that while the Cubs still have some interest in Bregman, they are not expected to make the highest offer.
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