Alex Bregman’s departure in free agency leaves the Boston Red Sox in a difficult spot. When the Red Sox signed Bregman last February to be their third baseman, it led to a rift with their incumbent star at the position, Rafael Devers. And when the Red Sox traded the disgruntled Devers to the San F rancisco Giants in June, many expected Boston to re-sign Bregman this winter and lock him in as a long-term franchise cornerstone. But seven months later, the Red Sox no longer employ Devers nor Bregman, who reached a contract with the Chicago Cubs over the weekend for five years and $175 million with deferrals. “Any time you are active in trying to bring a player in, it’s disappointing to lose out,” Craig Breslow, the Red Sox’s chief baseball officer, told MassLive in an email interview after Bregman’s decision. “We do this job because we are competitive and we want to deliver a championship to our fans, and falling short in a pursuit is an obstacle to that.” Bregman, who turns 32 in March, chose Chicago over a Red Sox offer reported to be for five years and $165 million with heavy deferrals. Bregman’s exit leaves a void in the Red Sox lineup, where he hit .273 with 18 home runs and an .821 OPS in 114 games, primarily batting second or third. It leaves a void at third base, where Bregman provided his typical above-average defense. And it leaves a void in the Boston clubhouse, where the battle-tested Bregman quickly emerged as a leader. Boston now must determine how to pivot. The top remaining free-agent infielder is Bo Bichette, a two-time All-Star who batted .311 with 18 home runs in 139 games for the Toronto Blue Jays last season. But Bichette, who turns 28 in March, is a career shortstop who has never played second or third base — the Red Sox’s biggest vacancies — in a regular-season game. He is expected to command a mega-contract that could exceed $300 million. Other options include free-agent third baseman Eugenio Suarez, who clubbed 49 homers in 2025 but is not the all-round hitter or defender that Bregman is. “We’ll be open to any way to improve our team,” Breslow told MassLive. “Free agency is an obvious path, but so are trades. We will try to continue to add offense, but leaning into pitching and defense is another way to boost our win total.” The Red Sox signed Bregman — a Scott Boras client — last winter to a three-year, $120 million contract with opt-outs. The deal paid immediate dividends, as Bregman helped lead Boston to an 89-73 record and its first postseason appearance in four years. But Bregman opted out after the Red Sox’s season-ending loss to the Yankees in the Wild Card round, making him one of the most in-demand players on the open market. Breslow declined to say whether Boston approached Bregman with a contract extension during the season or to speculate over why he selected Chicago. What is clear, however, is that the Red Sox have some heavy lifting to do if they’re going to build on last year’s success. Boston’s biggest swings of the offseason have been the additions of right-handed starter Sonny Gray and power-hitting first baseman Willson Contreras in separate trades with the St. Louis Cardinals. Gray, 36, figures to slot between ace Garrett Crochet and Brayan Bello in the Red Sox rotation, while the steady Contreras, 33, becomes one of the better bats in a Red Sox lineup that also includes Roman Anthony, Jarren Duran and Trevor Story. But on paper, the Red Sox aren’t as dangerous without Bregman in the heart of their order. And fans are still waiting for Boston to make a marquee splash with the money it saved by trading away Devers and the more than $250 million that was left on his contract. “This job requires balancing long and short term interests and making the best decisions for the organization, difficult as they [may] be,” Breslow said. “It means losing out on good players sometimes. However, while we will enter the ’26 season with different personnel, there will be no less resolve to compete for the division and make a deep [postseason] run.” ...read more read less