The Boston Red Sox's two most urgent needs this offseason are clear: a No. 2 starting pitcher to complement Garrett Crochet and another big bat (or two).
Re-signing Alex Bregman would do much to satisfy the latter requirement, but doing so won't be a walk in the park. The Red Sox will have to navigate the incessant leverage tactics of Bregman's super-agent Scott Boras, who will no doubt be pitting the Red Sox and Bregman's other suitors against one another.
Despite the negotiation maze ahead, the Red Sox are, in many pundits' minds, the front-runners to land Bregman, seeing as he's a perfect fit for Fenway Park and has already spent a year building meaningful relationships with Boston's staff and players.
Bregman belongs on the Red Sox. He's the ideal clubhouse leader for Boston's young talent (headlined by Roman Anthony), and the city has already embraced him. Red Sox legend David Ortiz recently discussed these qualities of Bregman with Scott Neville and Joey Copponi of the ITM Podcast, indicating that the Bregman-Boston relationship simply must continue.
When asked to send a message to Bregman ahead of his free-agent decision, Ortiz was crystal clear in his response. "Please come back!" Ortiz said in a playful tone, before lauding Bregman's leadership. Ortiz said that he gained a ton of respect for Bregman when he saw him continuing to communicate with and help Rafael Devers early in the 2025 season, even as Bregman and Devers were caught up in a position controversy that ultimately contributed to Devers's departure.
Red Sox legend David Ortiz wants Alex Bregman back in Boston, and he believes the Red Sox front office feels similarly
"Everybody loves him around here," Ortiz added about Bregman. "I haven't talked to the front office, but I'm pretty sure they're in the same boat that I am. They wanna keep (Bregman)."
Failing to re-sign Bregman would deflate the Red Sox. In just one season in Boston, Bregman became the de facto leader of the clubhouse (manager Alex Cora said so), which means his departure would force the Red Sox into completely recalibrating their clubhouse dynamic. That wouldn't be a step in the right direction in terms of winning now, nor would it be a productive development for guys like Anthony, Marcelo Mayer, and potentially Kristian Campbell in 2026. Each of those rising stars would benefit from a stable clubhouse mechanism to develop within, with Bregman as the ideal guiding light.
It almost sounds like Bregman's being described as a coach here, which isn't off-base, considering Anthony himself said in July that Bregman was effectively acting as a coach in the Red Sox dugout while injured.
But let's not forget about Bregman the player, either, whose absence from Boston's lineup would be a loss of production that would be difficult for the Red Sox to make up for in 2026, even if they landed Pete Alonso this winter. 'Why not both?' many Red Sox fans are wondering when it comes to Bregman and Alonso. It's a valid question that chief baseball officer Craig Breslow should be ruminating on daily.