Why Did Alex Bregman Choose Boston?

Last night, the Boston media market was flooded with reports that the Red Sox and star third baseman Alex Bregman had agreed to a three-year, $120-million contract with opt-outs after the first two seasons. On the surface, this deal is incredibly surprising. It had been reported multiple times that Bregman and his agent, Scott Boras, were seeking a contract length of five to six years, a number it was assumed most teams were hesitant to give a player entering his age-31 season on a somewhat down note.

However, it seems that at least two teams were willing to hand out a longer-term commitment to Bregman than the Red Sox. Bob Nightengale reported that the Cubs offered four years and $120 million, while Evan Petzold reported the Tigers offered six years and $171.5 million. With longer commitments, and more money sitting in front of him, what made Bregman choose to call Boston home for (possibly) the next three years?

The Alex Cora Connection
Alex Cora clearly wanted Alex Bregman in Boston. Cora never shied away from speaking about Bregman in the media, especially at Fenway Fest last month. Cora even mentioned he foresaw Bregman being a Gold Glove-caliber second baseman, the position he likely slots into as the roster currently stands. While there was speculation that the relationship between Cora and Bregman had soured after Cora left the Houston Astros, it’s obvious that the two hold a mutual respect. Sure, Detroit has A.J. Hinch, but Cora seems to be highly respected among former players. Plus, Boston has a couple other benefits that Detroit and Chicago couldn’t offer.

Possible Number Bump
As I’ve outlined before, Alex Bregman’s numbers faded during the 2024 season. However, if we look at his home game spray chart overlaid onto Fenway Park, we see a different story. Multiple outs have turned into either wall ball doubles or home runs and we even see a few outs in right field that would likely scrape over the short wall there. If we do the same to both Wrigley Field and Comerica Park, there are more doubles turned into outs than outs turned into home runs. Bregman is betting on himself to deliver some power numbers with the Red Sox and he should make the Green Monster his best friend in 2025.

Dollars and Cents
Let's make sure we appreciate how big the dollar values are here. Some of the money (we don't yet know how much) in Bregman's contract is been deferred, but it's important to remember that it will only be deferred for three years, meaning that the overall value of the contract probably won't be affected that much. Bregman's average annual value of $40 million ties him with Aaron Judge at sixth place on the list of highest AAV ever handed out. There's always a tradeoff: Players want long-term security, while teams don't want to be saddled with a big contract if things turn out badly. In exchange for taking this shorter deal, Bregman is getting paid like one of the absolute best players in the game. The opt-outs also increase the value of the deal in a big way. If he puts up a tremendous season and thinks he can beat these terms, Bregman can go right back on the market and look for a long-term deal once again. This is an extremely valuable deal.

A Promising Young Core
The Red Sox have one of the top-ranked farm systems in baseball, with three top prospects knocking on the door to the majors. They just made a major trade for a likely playoff game one starter with Garrett Crochet and brought in another World Series champion in Walker Buehler. The front office finally seems serious about winning and believes in the young core to help push the team over the edge. Adding a veteran presence and clubhouse leader like Bregman gives that core someone strong to lean on and listen to while they develop into their own as baseball players. The Red Sox are young and about to get younger. If the prospects even sniff half of what they are believed to be able to accomplish early in their careers, that had to look very enticing to someone like Bregman.

While the deal seemed to come out of nowhere on Wednesday night, adding Bregman on a three-year deal makes a lot of sense. He turned down longer (and likely more profitable) contracts in places that don’t fit his play style as well. For the Red Sox, this deal is the clearest indicator we've seen that finally, winning is at the forefront of the decision-making process.