Inside The Red Sox

Alex Bregman 'Dark Horse' Suitor Is Red Sox Nightmare

Will the Boston Red Sox find a way to retain Alex Bregman?
Aug 22, 2025; Bronx, New York, USA;  Boston Red Sox third baseman Alex Bregman (2) prior to the game against the New York Yankees at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images
Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) prior to the game against the New York Yankees at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

The longer Alex Bregman remains on the open market, the more nerve-wracking the sweepstakes is for the organization.

It's no secret that Bregman was everything the club could've asked for in 2025. Bregman bet on himself with a short-term deal with opts-outs and responded with a big season. Now, he only was able to play in 114 games due to a quad injury, but he was great when healthy. Bregman slashed .273/.360/.462 with 18 homers, 62 RBIs, and 28 doubles. Bregman had his highest OPS (.821) and batting average (.273) since 2019 when he finished in second place in the American League Most Valuable Player race.

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Boston's biggest need right now is another big bat in the middle of the order and the club has a hole in the infield. Check and check if the club can re-sign Bregman. But there are other teams to worry about. FanSided's Robert Murray shared an in-depth look at Bregman's market on Monday and one thing that should make Boston fans nervous is the fact that Murray called the Blue Jays the "dark horse" option for Bregman.

Boston is one move away

"The dark horse: Toronto Blue Jays," Murray said. "The Jays have been connected to Bregman, Kyle Tucker and Bo Bichette this offseason. Bichette should be the priority – he’s younger and Toronto knows what it has in its star infielder – and it’s very likely that Bregman is the fallback if they aren’t able to retain Bichette. Still, Toronto is big-game hunting, and this feels like the offseason they land a big name in free agency."

Boston should be viewed the same way that teams like Toronto, the Los Angeles Dodgers, the New York Mets, and the Philadelphia Phillies are. The Red Sox are a big-market team and have plenty of money at their disposal. They should be viewed as the big threat, not the reverse.

But the Blue Jays are operating like a big-market team and already have handed out a $210 million deal to Dylan Cease. That hasn't slowed them down, though. If anything, the pact has them getting more aggressive. The Blue Jays consistently have been linked to Kyle Tucker, Bo Bichette, and now Bregman.

If the Blue Jays land Bregman, that would be a nightmare scenario. The vibe around the fanbase right now is tense, to say the least. Imagine if the Red Sox lowball Bregman and miss out to another AL East rival? That was the case with Pete Alonso and the Baltimore Orioles. At least Alonso didn't help Boston get to the playoffs in 2025. Bregman did and if the Red Sox let him walk and he goes to Toronto, it would be pretty difficult to justify a decision like that.

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Patrick McAvoy
PATRICK MCAVOY

Patrick McAvoy's experiences include local and national sports coverage at the New England Sports Network with a focus on baseball and basketball. Outside of journalism, Patrick received an MBA at Brandeis University. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scottneville21@gmail.com

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