The Boston Red Sox won the Alex Bregman sweepstakes last year, landing the star on a three-year deal worth $120 million with opt outs after each season. Now, Bregman is expected to opt out of his deal after one year in Boston and Spotrac projects him to sign for $100 million over four years this winter, which seems like quite a low projection.
Considering Bregman would be opting out of two years and $80 million to hit free agency, he would need to be fairly confident in landing a deal much bigger than Spotrac’s projection. In reality, the number will likely be closer to $200 million than $100 million.
Bleacher Report’s Tim Kelly recently favored the Red Sox in the next Bregman sweepstakes, and it seems to make a lot of sense.
“While there will certainly be other suitors, Bregman remaining in Boston for the foreseeable future is still the scenario that makes the most sense, by far,” Kelly wrote. “Yes, at times it feels like the Red Sox have too much young position talent for their own good, but keeping that makes the veteran presence of Bregman that much more important. They also burned the bridge with Rafael Devers, so there’s not a good internal option to replace Bregman at third base in 2026.
“Alex Cora wanted to reunite with Bregman last offseason, so much so that the Red Sox gave up draft-pick compensation to sign him. With Devers gone and no ability to give Bregman a QO, the Red Sox should be the most motivated player in the sweepstakes for Bregman.”
The Red Sox make sense as the top suitor, especilly if Spotrac is accurate. As noted before, Spotrac’s projection is likely very low for Bregman, though.
Either way, the Red Sox need to do everything in their power to bring Bregman back to Fenway Park.
In one season with the team, he quickly became a fan favorite and helped spark the offense when he was on the field. He’s going to be the most important storyline in Boston sports until the veteran signs a new contract. The Red Sox would love if it was worth $100 million, but the star is likely looking for more.
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Red Sox Insider Sounds Alex Bregman Alarm Ahead Of Impending Opt-Out
Is a one-and-done for Bregman in Boston a growing possibility?
Aug 12, 2025; Houston, Texas, USA; Boston Red Sox third baseman Alex Bregman (2) runs to first base on a single during the ninth inning against the Houston Astros at Daikin Park. Mandatory Credit: Troy Taormina-Imagn Images / Troy Taormina-Imagn Images
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The Boston Red Sox had quite an exciting offseason and season over the last year, but this winter’s offseason could be even more exciting.
Boston has multiple pieces from their 2025 club who are set to land in free agency, headlined by Alex Bregman. The Red Sox could look to bring some of their guys back, but they could also sign outside players to help bolster the roster.
Bleacher Report’s Tim Kelly recently discussed Lucas Giolito as a free agent and listed the Red Sox starter as one of the top 10 starting pitchers in free agency this winter.
Lucas Giolito could be headed for a solid contract in free agency
“We didn’t put players with options that are sure to be exercised—like Chris Sale and Freddy Peralta—on this list. Giolito has a mutual $19 million option for 2025, and both the pitcher and the Boston Red Sox could go either way on that,” Kelly wrote. “The most likely scenario is that Giolito declines the option, because if he does, the Red Sox could very well extend a one-year qualifying offer to him, which would pay him around $22 million. Again, it’s possible he takes that. It’s also possible he declines it, or even that the Red Sox don’t extend it to him. There are a lot of moving parts here.
“If Giolito gets to the open market, he pitched very well after missing the entirety of the 2024 season after undergoing an internal brace procedure on his right elbow. Giolito wasn’t available for what turned out to be a brief postseason run with the Red Sox because his elbow flared up. Ultimately, pretty much all of this is contingent on him being healthy heading into the offseason.”
Giolito’s free agency is likely going to hinge on his health. He can accept the qualifying offer from the Red Sox, if they extend it, and nobody would bat an eye. Signing back with Boston for over $20 million on a one-year deal would work well for both sides.
But Giolito could decline the qualifying offer and bet on himself in free agency. There’s a chance he’s chasing a three- or four-year contract worth around $20 million a year.
In the past few offseasons, there have been numerous free agent pitchers sign for over $60 million or $70 million, with Giolito being better than multiple big contract pitchers.
