Troubling Alex Bregman update is a bad sign for Red Sox's reunion pursuit

MLB: OCT 02 AL Wild Card - Red Sox at Yankees
MLB: OCT 02 AL Wild Card - Red Sox at Yankees | Icon Sportswire/GettyImages

The 2025-26 MLB offseason is about halfway through, spring training is on the horizon, and the Boston Red Sox still need to bolster their offense to be competitive in the American League East next season. Fortunately for them, the infield market is moving rather slowly.

Alex Bregman remains a free agent and Boston is pursuing a reunion with him. Alongside trade acquisition Willson Contreras, he'll bring a right-handed bat, solid defense and years of experience to the Red Sox's batting order, which they learned last year when he fit so well with the club.

Of course, the Sox aren't the only team courting the two-time World Series champion and its reunion bid could be under threat. According to a New Year's Day report from MLB insider Mark Feinsand, sources say the Toronto Blue Jays and Arizona Diamondbacks are the most aggressive teams in the race for Bregman's services.

Feinsand believes a reunion with Boston is still on the table, but in many fans' eyes, it should be the only option. Not only have the Red Sox gone the entire offseason so far without signing a major league free agent, they traded Rafael Devers to accommodate Bregman last season, which they should not forget so quickly.

Insider Mark Feinsand reports that Blue Jays and Diamondbacks are most aggressive teams in Alex Bregman's market, leaving Red Sox in the dust

The Blue Jays and Diamondbacks each have compelling (concerning, in Sox fans' eyes) cases to lure Bregman to their team. Toronto and Arizona are in two of the most competitive divisions in baseball and both have been to the World Series in the last three seasons. The Jays last season signed Vladimir Guerrero Jr. to a 14-year, $500 million extension and this winter they took a huge leap by signing Dylan Cease to a seven-year $210 million deal — their commitment to winning has been palpable.

Bregman signing with Toronto would be a complete disaster, since it's a division rival and they would face him in four series per year for the duration of his contract. Boston letting him walk to any other team would still be a dissapointment after the Devers trade, the offseason's promises and his fit with the club last season.

The Red Sox are going to have to get uncomfortable to sign any top free agent. Their hesitance to spend money won't fly — and historically hasn't flown — in the AL East, especially now that the Blue Jays and Orioles are flexing their spending muscles.

In 2025, Bregman showed that he belonged in Boston, despite a subpar second half performance. He's the best all-around third baseman available, and the Red Sox need all the help they can get defensively and with offensive consistency.

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