The Boston Red Sox are fighting an uphill battle to bring back Alex Bregman this winter. There are bound to be more than a handful of teams in his sweepstakes, but the Red Sox could have an edge as the incumbent team.
The biggest issue that could arise is the money. The Red Sox might not want to give Bregman a six- or seven-year contract that will take him past his prime, while a few desperate teams might be willing to do so.
The Athletic’s Jim Bowden recently predicted Bregman would bolt from Boston and sign a huge six-year, $182 million deal with the Detroit Tigers.

“The Tigers just missed on Bregman last winter, but they won’t this time around. Bregman would bring his leadership, mentoring abilities and winning qualities to the Tigers’ clubhouse,” Bowden wrote. “Fun fact: The Tigers haven’t had a team captain since George Moriarty, who had the role from 1912-15. If they sign Bregman, would he become the first in over 100 years?”
Bregman should be among the Red Sox’s top priorities, but they could also pursue a slugger like Pete Alonso to take his spot in the lineup.
As a result, a team like the Tigers could become desperate enough to give Bregman a $182 million deal like Bowden projects.
The Tigers have been closely connected to Bregman for over a year now. This winter could be the time they finally take the shot and add the star. Bregman would certainly bolster their lineup quite a bit.
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