BOSTON — Alex Bregman ’s time with the Red Sox is over after one season.
Bregman agreed to a five-year, $175 million contract with the Cubs late Saturday, as first reported by Jon Heyman of the New York Post and ESPN’s Jeff Passan . There are no opt-outs in the deal, which reportedly includes deferrals. The Red Sox were said to make an aggressive offer for Bregman but did not land him, leaving a sizable hole in the club’s lineup after a single year.
A reunion with Bregman, who opted out after the first season of the three-year, $120 million deal he signed with the Red Sox in February, was thought to be a top priority for the Red Sox this winter. After trading for Sonny Gray and Johan Oviedo to fortify the rotation and acquiring Willson Contreras from St. Louis to start at first base, Boston turned its sights to the free agent market, where Bregman and longtime Blue Jays shortstop Bo Bichette were the top two unsigned infielders. A reunion with Bregman always seemed like the most likely outcome, though other teams — including the Diamondbacks and Blue Jays in addition to the Cubs — pursued the soon-to-be 32-year-old.
The Red Sox were involved in Bregman’s market until the end, a source said, and willing to offer him five guaranteed years at an annual rate in the ballpark of what he received. Ultimately, while the Red Sox made what they felt was an aggressive offer to Bregman, the Cubs outbid them by guaranteeing $35 million per year over a five-year term. It was simply a matter of dollars, and not term, at the end of the bidding, with Chicago offering more on an annual basis.
Both offers included significant deferrals and Bregman’s deal with the Cubs includes $70 million in deferred money, according to The Athletic . Boston was not willing to include a full no-trade clause, which the Cubs were. That was a sticking point as well.
Bregman, a longtime Astro who won two World Series titles with that club, left Houston last winter to sign a short-term pact with the Red Sox in an effort to re-establish himself for a second turn through free agency. He got off to a stellar start in Boston, hitting .299 with 11 homers, 17 doubles, 35 RBIs and a .938 OPS in his first 51 games before suffering a quad strain that kept him out seven weeks. He returned for the final 63 games of the season and hit .250 with seven homers, 27 RBIs and a .724 OPS while at times not looking 100% healthy. In total, Bregman hit .273 with an .821 OPS in 114 games in a Red Sox uniform. He was selected to the American League All-Star team for the third time in his career.
Throughout the season, Bregman discussed how he loved being with the Red Sox and was interested in exploring a long-term arrangement to stay . Still, with a desire to land long-term financial security in the form of a deal that would take him deep into his thirties, he elected to once again hit free agency in November. The short length of his tenure with the Red Sox is sure to raise questions, retroactively, about the controversial June trade of Rafael Devers , who was only displaced — and ultimately, frustrated — because Bregman was brought in to play third base. It’s another example of the Red Sox — the only club in baseball to not sign a major league free agent this year — losing out on a bidding war. Once again, after years of clubhouse turnover, Boston is losing key leadership behind the scenes, as well. Bregman was a mentor to young players like Roman Anthony and Marcelo Mayer and formed the core of the team’s leadership group alongside Trevor Story and Rob Refsnyder (who also has departed in free agency).
“I came up at a time when he was hurt and he was basically like a coach. He was like another hidden coach for me,” Anthony said Saturday at Fenway Fest. “When I came up and got into that DH role a little bit after we made that trade, he was sitting next to me every second of the game constantly showing me different things and helping me prepare. I can’t speak highly enough about him and what he does as a leader.”
With Bregman out of the mix and others (like Ketel Marte , who won’t be traded by Arizona ) off the market, the Red Sox will have to pivot in their efforts to secure a major offensive addition before Opening Day. Bichette remains unsigned and is a clear possibility, though there are other motivated suitors, including the Phillies , known to be interested in him. Trade candidates like St. Louis’ Brendan Donovan and free agents like Eugenio Suárez remain available, too, and there’s a chance the Cubs will trade either Matt Shaw or Nico Hoerner with Bregman now in the fold. Bregman was clearly the team’s Plan A with a month to go, so his decision will necessitate a change of plans.
“You guys know how I feel about him. Last year, he checked all the boxes I knew he was gonna check and he checked some boxes people didn’t know he was going to check,” manager Alex Cora said hours before the news of Bregman’s departure broke. “The ball is in his court.”
Bregman’s departure also increases the importance of Mayer to Boston’s roster in 2026. The 23-year-old, who debuted last season, seems likely to begin the year at either second base or third base, depending on who else the Red Sox acquire. Last season, with Bregman out, Mayer admirably manned third base after debuting, impressing defensively in 39 games (28 starts) at the hot corner. On Saturday, he said he was preparing at both positions as spring training nears.
The Sox remain likely to add either a second baseman or third baseman via free agency or trade but their options have dwindled. Their payroll is currently projected right around the first competitive balance tax (CBT) threshold of $244 million and it’s unclear if they are willing to go over the next threshold – and incur more penalties – at $264 million.
“We don’t like to talk about our budget planning, but we’ve been here for 24 years and we’ve been over the CBT threshold,” team president Sam Kennedy said Saturday. “We were over the CBT threshold last year. We’ve been over the CBT threshold in years past. We’ve been under. So it’s to be determined, but we’ll see where things shake out.”
Bregman was not eligible to receive a qualifying offer this year after declining one from Houston a year ago, so the Red Sox will not receive draft pick compensation for him leaving. Boston will not get a chance to face off against Bregman and his new team for a while, either, as the Red Sox and Cubs aren’t set to meet until the final weekend of the regular season, when they close the schedule with a three-game series at Fenway Park from September 25-27.
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