Until recently, Pete Alonso felt like a perfect fit for the Red Sox. His profile suited him effortlessly for Boston and its ballpark. However, AL rival Baltimore Orioles outbid the Red Sox with a 5-year, $155 million offer and won the bidding in the Alonso sweepstakes. As one prominent agent said, not about Alonso, but in general, “[The Red Sox] don’t believe in long-term deals.” And holding firm to that mindset might make it harder for them to land Alex Bregman, too.

The last time this team made a big long-term commitment in free agency was in March 2022. They signed Trevor Story to a six-year, $140 million deal under Chaim Bloom. Since then, the Red Sox have offered only one contract longer than three years. It was a five-year, $90 million deal for Japanese phenom Masataka Yoshida. Even

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