Despite being the favorite to re-sign Alex Bregman during the entire offseason, the Boston Red Sox failed to close a deal for a third baseman. Bregman signed a five-year, $175 million contract with the Chicago Cubs.
This entire free agency drama was perfectly summarized by former Red Sox star Jonathan Papelbon using an analogy of a bar where the Red Sox were the guy who entered with "hot ch*ck" Alex Bregman, before the other guy Cubs, came in to swoop the third baseman.
"I don't know how y'all feel, but I feel like I did in college when I walked into a bar and there's this hot ch*ck there, and you waited to go up and talk to her," Papelbon said on Foul Territory. "And then somebody else came in and swooped in, talked to her, and now she's gone. She left the bar with him. So that's how I feel right now."
Losing out on Alex Bregman is like having a "hot chick" get stolen from you at a college bar, says @TheRealJPap58. Pic.twitter.com/8SyTG5iQ13
— Foul Territory (@FoulTerritoryTV) January 12, 2026
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Jonathan Papelbon reveals reason why Alex Bregman chose Cubs over Red Sox
Jonathan Papelbon had the perfect analogy as the Red Sox were doing everything right in their efforts to re-sign Alex Bregman, but the minute a new offer came in from the Cubs, they couldn't improvise.
Bregman's camp reportedly notified the Red Sox about the new offer, hoping they would match it or upbid it. The Red Sox did improve their offer to five years, $165 million. While it was $10 million short of the Cubs' offer, Papelbon believes the other components of the contract also played a part in Bregman's decision.
"The no-trade clause, to me, was the final factor and decision-maker in this," Papelbon said.
The Cubs' contract was much better than the one from the Red Sox, as it contained a full no-trade clause and no opt-outs.
Bregman is a family man, husband to entrepreneur Reagan, and father to two young sons, Knox and Bennett. It's expected that he would want to stay at a place where he could call home for the next five years. The no-trade clause ensured that Bregman can have control over where he wants to play for at least the next five years.
With Bregman gone, the Red Sox will need to get creative for the remainder of the offseason as they still need to address their infield.
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