The Boston Red Sox have been linked to Alex Bregman as their ideal right-handed addition to their lefty-heavy squad since they lost out on Juan Soto.
It has long been established that Bregman hopes for a long-term deal in the $200 million range. It has even longer been established that Boston won't pay out long-term deals with experienced free agents, even if they're the best fit remaining on the market.
Bregman is definitely that, with his history of success at Fenway Park (.375/.490/.750 slash line, 1.240 OPS, seven homers in 21 career appearances) and rock-solid infield defense. Bregman's fit in Boston long-term is a different question, but after losing 31 homers of production when Tyler O'Neill signed with the Orioles, and it needs to make up for it somehow, some way.
Recent updates that Bregman's market has reopened to the Astros and Boston won't give him more than a four-year deal have Sox fans less than optimistic that the team will sign the third baseman. On the Jan. 28 installment of "The Michael Kay Show," MLB insider Jeff Passan validated Red Sox Nation's suspicions.
Jeff Passan dashes Red Sox fans' hopes of landing Alex Bregman with latest update
"I don't think Boston is particularly likely to happen at this point," Passan said of Bregman's potential suitors.
He named Houston as the most probable fit — although he's unsure if it'll budge from its initial six-year, $156 million offer — but noted that the Blue Jays need the most help of the teams courting the infielder. The Tigers are also still in on Bregman, but they have the smallest budget of the teams in the running (seemingly, besides the Red Sox).
If Boston made an effort to sign Teoscar Hernández or Anthony Santander to fill its offensive vacancy with less money and a shorter deal while still acquiring one of the best free agents on the market, it wouldn't be in this position. Now, the Red Sox will have to turn to J. D. Martinez, Randal Grichuk, Pete Alonso, Ha-Seong Kim, or any number of lower-tier free agents to bolster their offense.
I don't fault the Red Sox for not being willing to go past four years for Alex Bregman...
— Chris Cotillo (@ChrisCotillo) January 28, 2025
But it's the same story time after time. Gotta get uncomfortable one of these days.
From a new @FenwayRundown with @Sean_McAdam: pic.twitter.com/ikDDEC8RY5
Bregman isn't a perfect fit for the Red Sox now, and it'll be an even less ideal fit a few years down the road with plenty of infield prospects on their way to the majors. But the front office attested that there is extreme internal urgency to return to the playoffs and become a 90-95 win team and that it was willing to "get uncomfortable" to make those things happen.
Signing long-term deals for players, especially those on the so-called "wrong" side of 30, is uncomfortable as regression and injury become more likely. But missing the playoffs for a fourth-straight season and the sixth time in seven years should make the Red Sox front office even more uncomfortable than that. Boston could be headed for that fate in a wide-open American League one year after their bitter rival made it to the World Series, and that's unacceptable.
Every year the Red Sox miss the playoffs and continue to whiff on their top free agents, they become an even less appealing destination to future free agents and trade candidates. At a certain point, they need to bite the bullet and stop trying to win every single deal with flying colors because it's only worked a handful of times. Based on Passan's comments, their pursuit of Bregman is almost sure to be yet another tick in the "loss" column for one of the biggest markets in baseball.