On Feb. 12, the Boston Red Sox made their first big-market move in years by signing Alex Bregman. Their pursuit of the veteran was long, as he hoped for a long-term deal, but his market was small enough that Boston became his best option after months of negotiation with five different clubs.
Bregman signed a three-year, $120 million deal with opt-outs after each of the first two seasons and deferred money included. The Red Sox hadn’t spent more than $21.05 million on any single free agent transaction this offseason, and the Bregman signing is one of their largest in years if he doesn’t opt out after season one.
Boston’s CEO and president Sam Kennedy mentioned that the front office was willing to go over the luxury tax threshold to compete in 2025, and it’s done it for the first time since 2022. As the Yankees, Dodgers and Mets pushed the boundaries of their payrolls to make deep postseason runs and win World Series, the Red Sox were left in the dust among the mid-market teams. John Henry is still no Mark Walter in terms of recent spending, but the Bregman deal puts him back in the conversation after three straight playoff misses.
Henry seems to agree. After the Red Sox inked Bregman on Feb. 12, his wife, Linda Pizzuti-Henry, posted a picture of the Fenway Sports Group owner sparking a cigar in an armchair by his fireplace. Red Sox Nation has interpreted the picture in different ways, but it’s an interesting celebration for a three-year deal.
John Henry’s celebratory cigar after Alex Bregman signing divides Red Sox fans
The excitment about the Red Sox’s reported Alex Bregman agreement was felt all the from the top of the organization. https://t.co/PNaeFykHJp
— NESN (@NESN) February 13, 2025
Don’t get us wrong: we don’t mean to sound unimpressed or unappreciative of the Bregman signing. The Red Sox played the waiting game, and it worked out incredibly well for them. Bregman isn’t a perfect fit in Boston, as it already has an everyday third baseman with no place to move him and plenty of infield prospects on the way, but he makes the team much better in the short term, which is what matters for 2025.
But Henry’s Red Sox of old wouldn’t celebrate a three-year deal with opt-outs after each season. Boston won all of its World Series with a top-four payroll in the league, and its recent decrease in payroll corresponds with the team’s five playoff misses in the last six seasons.
Signing Bregman is, no doubt, a step in the right direction for the Red Sox. They won the deal, but missed so many better ones in the last seven years since they were regular postseason contenders. Red Sox fans would prefer cigars be smoked after World Series wins, not desperately needed free agent signings.
We’ll revisit this celebration in October when, hopefully, Bregman helps the Red Sox make a deep postseason run.
