The Boston Red Sox went into the winter meetings with a few big free agents in their sights, but they whiffed on both Pete Alonso and Kyle Schwarber. Alonso signed with the rival Baltimore Orioles while Schwarber landed a new deal with the Philadelphia Phillies.
This leaves the Red Sox chasing a few other top free agents, including a new contract with superstar third baseman Alex Bregman.
Bleacher Report’s Tim Kelly predicted on Friday that the Red Sox would re-sign Bregman on a huge five-year, $135 million deal this offseason.

“It can be argued whether Schwarber or Alonso would have been a better fit for the Red Sox given their power production, but both signed elsewhere,” Kelly wrote. “In what projects right now to be a very left-handed lineup, chief baseball officer Craig Breslow might be best off circling back to the right-handed hitting Bregman.
“Another thing to consider is Bregman was ineligible for the qualifying offer after receiving one last winter. So if Bregman leaves, Boston won’t get anything in return. That’s another reason to retain the three-time All-Star.”
Bregman is one of the best bats left on the market this winter. He’s reportedly receiving interest from multiple clubs, including the Detroit Tigers and Chicago Cubs.
But the Red Sox have the money and familiarity with Bregman to land a new deal. He was a fan favorite in Boston this year, and the front office could reward him with a huge new deal. The Red Sox seem reluctant to give him a long-term deal, but they might need to do it to secure him in Boston.
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