After signing a three-year deal with an impressive $40 million in average annual value, making him one of baseball's highest-paid stars in 2025, Alex Bregman only lasted one season with the Boston Red Sox.
The third baseman on January 10 signed with the Chicago Cubs on a five-year, $175 million deal, $10 million more than Boston was willing to offer. The Red Sox also wouldn't budge on their refusal to extend Bregman a full no-trade clause, which Chicago happily did.
It's clear why Bregman would demand such a thing after watching the Red Sox trade Rafael Devers away in June with no clear backup plan. Bregman was clearly Boston's first choice, but it didn't take its pursuit seriously in more ways than one.
Besides not offering him the no-trade clause, the Red Sox did not approach Bregman about an extension during the season, according to Chris Cotillo in an exclusive interview with TalkSox. Had Boston offered him five years at $150 million during the season, Cotillo feels Bregman may have accepted.
Red Sox should've approached Alex Bregman with an extension offer immediately after Rafael Devers trade to avoid offseason loss
The Red Sox should've tried to extend Bregman immediately after the Devers trade. They moved Devers in to accommodate him at third base in the first place, and approaching him with an extension midseason would've been a welcome and easy way to show their commitment to him long-term. And, if Cotillo's estimate is correct, they could've signed him for $15 million less than they offered this winter and $25 million less than Chicago will give him.
Instead, Boston waited until the offseason to pursue Bregman, which showed that it was willing to take the risk of losing him to another team and having no full time third baseman for next season and beyond. Bregman, and likely every other free agent, has seen the Red Sox's repeated failures to land the top players on the market, and after they failed to approach him with an extension offer, he saw just how irresponsible and unserious they could be.
Bregman was injured and on the sidelines at the time Devers was traded, and he missed nearly six weeks of playing time — the first year of his contract with Boston didn't go exactly as planned. Still, it should've seen the writing on the wall that Bregman planned to opt out of his deal. He sought a long-term deal before he signed with the Red Sox the first time, and if he felt like he could get it elsewhere, he was absolutely going to opt out to test the water.
The Red Sox could've beaten the Cubs' offer and they could've given Bregman the no-trade clause. But since everything has to be done on John Henry's terms, despite his team needing players more than they need it, Boston lost out again.