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Red Sox president is being heavily criticized over Alex Bregman comments

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Anyone who knows me, or reads my MLB stuff when the Red Sox are involved, knows that I’m no fan of Owner John Henry, or management…especially President Sam Kennedy and Chief Baseball Officer Craig Breslow. I wasn’t a fan of his predecessor, Chaim Bloom, either. I’m more of a Dave Dombrowski guy.

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But I have to stick up for Kennedy. The Sox are known for putting their foot in their mouths during press conferences and speeches. A couple of years ago, the team’s Chairman, Tom Werner, famously said the team would be “Full Throttle” during free agency, and then little to nothing. Last week, Kennedy was asked about the loss of Alex Bregman, and he blurted out, “Ultimately, if Bregman wanted to be here, he’d be here”. Since then, he’s taken a ton of grief from the local press. The next day, he tried to smooth it over by complimenting Bregman, even saying how great his family is, and wishing him nothing but the best in Chicago.

Boston Red Sox third baseman Alex Bregman bats against the Detroit Tigers during the first inning at Comerica Park, May 14, 2025.

Initial Contract:

Normally, I side with players when it comes to contract negotiations, and believe a player should get whatever he can…and to a degree, I feel that way about Bregman too. But, in this case, I have to defend what Kennedy said. The Sox initially signed Bregman to a 3yr/$120M contract (an overpay in my opinion), with a player opt-out after yr. 1 and yr. 2. I never saw Bregman as a $40M player, but good for him…a player is worth whatever a team will pay him. Oftentimes, a team has to overpay to get the player.

In good faith, the Sox gave him the deal with the opt-out clauses, realizing there was a chance he’d walk. In his last season with the Astros, he missed 17 games, yet the Sox still offered him the best deal. And last season he missed a whopping 48 games with a recurring hamstring injury…at age 31. 

With $80M waiting for him in the 2026 and 2027 seasons, Bregman decided to say “No Thank You, it’s getting late to come up for coffee”…ala George Costanza. I believe it was in this context that Kennedy spoke, and I wish he had just elaborated and said that. The reality is, with the Sox’s recent aversion to salary, as evidenced by trading Rafael Devers, they probably weren’t all that upset that he decided to opt out.

Boston Red Sox third baseman Alex Bregman fields his position against the Detroit Tigers at Comerica Park, May 14, 2025.

The Opt Out:

By opting out, it was Bregman who made the decision to leave the Red Sox. He said no to $80M, and took the risk, so good for him for betting on himself and winning…but when Kennedy said, “If he wanted to be here, he would be here”, was 100% accurate. The Sox were under no obligation to renegotiate with him and offer him more money after he ripped up the current contract he was on.

But let’s analyze his new deal with the Cubs. It is for 5yr/$175M. His deal with the Sox and Cubs each has deferred money. His new deal with the Cubs has no opt-outs, and has a no-trade clause…something that the Sox weren’t willing to do. Over the next two years, Bregman will actually lose $10M, because he would have gotten $80M from the Sox, but now, he will be getting $70M over the next two years. 

From 2028-30, he’ll be making $105M over those three seasons. But with the initial $10M loss, his net over those three years is only $95M. The reality is, if Bregman honored his deal with the Sox, he realistically would have gotten at least $95M from someone after the 2027 season ended. 

Did he cost himself money?

By that time, he’ll be 34 yrs old, and would have been able to grab a solid contract, assuming he continues to put up decent numbers over the next two years. The ironic part of this is that after his current contract ends, he’ll be entering his age-37 season and most likely not getting many multi-year or high-value deals. But if he stayed with the Sox, he would have banked that extra $10M, and still been in line for one more multi-year, high-value contract, entering his age-34 season. By trying to squeeze every nickel, he may have cost himself millions in the long run.

Jan 15, 2026; Chicago, Illinois, USA; L-R Scott Boras, Alex Bergman and Jed Hoyer as Bregman is introduced as a new Chicago Cubs player at a press conference at Wrigley Field. Mandatory Credit: David Banks-Imagn Images

In what could have and should have been a PR win, Kennedy turned it into a disaster. For a guy coming off a now chronic injury, that cost Bregman 48 games last season, not re-signing him wasn’t the worst decision in the world. Kennedy should not have run away from his statement; he should have doubled down on it. 

In this rarest of times, I agree with his statement, and I fully support Kennedy and all of Sox management by not resigning him.

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The post Red Sox president is being heavily criticized over Alex Bregman comments appeared first on The Big Lead.

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