Inside The Red Sox

Red Sox's Alex Bregman Backup Plan Destined To Fail, Evidence Suggests

Bo Bichette is nobody's backup plan...
Apr 29, 2025; Toronto, Ontario, CAN; Toronto Blue Jays shortstop Bo Bichette (11) gets caught trying to steal third base against Boston Red Sox third baseman Alex Bregman (2) during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images
Apr 29, 2025; Toronto, Ontario, CAN; Toronto Blue Jays shortstop Bo Bichette (11) gets caught trying to steal third base against Boston Red Sox third baseman Alex Bregman (2) during the first inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | John E. Sokolowski-Imagn Images

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Anyone else having a difficult time envisioning the Boston Red Sox successfully pivoting off Alex Bregman to sign Bo Bichette?

On Saturday night, Bregman reportedly agreed to a five-year, $175 million deal with the Chicago Cubs, who were outbid by the Red Sox for the same player just 11 months ago. In the immediate aftermath, every story written about the deal from a Boston perspective suggested that Boston would pursue Bichette, the Toronto Blue Jays' two-time All-Star shortstop.

The Red Sox might well intensify their efforts to sign Bichette from this point forward. But it would be foolhardy to put much stock into them acquiring him.

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It's hard to believe Red Sox would sign Bichette now

First, the Red Sox are pivoting to Bichette at a time when everyone else is doing the same. The Philadelphia Phillies' interest in Bichette just intensified to the point that they're having their first meeting with him on Monday. The New York Yankees also reportedly started preparing for Cody Bellinger to sign elsewhere and will likely redouble their Bichette efforts.

Bichette isn't the type of free agent you can afford to treat as a backup plan. Even if he understands why the Red Sox waited until after Bregman was gone to make their best offer, he won't be sympathetic to any ideas they have about saving a buck or two.

Bichette had to be salivating over the contract Bregman got on Saturday night. He's four years younger, and in all likelihood, he'll get more total dollars than the new Cubs third baseman, even if the average annual value of the deal is slightly lower.

And then again, maybe that AAV won't be lower, in which case the minimum price for Bichette would figure to be six years, $210 million. Boston hasn't given out a $200 million deal to a free agent since Dave Dombrowski was running the show (David Price, 2016).

Bregman was the Red Sox's biggest free-agent win of the decade so far, and his was a unique situation because he chose to take a pillow contract. That might be what the Red Sox are hoping Bichette will do, but it feels like he has too much interest right now.

Nothing the Red Sox have done in the last six years suggests that they'll register the highest bid for Bichette. The Red Sox should feel free to prove that statement wrong, but we're not holding our breaths.

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Jackson Roberts
JACKSON ROBERTS

Jackson Roberts is a former Division III All-Region DH who now writes and talks about sports for a living. A Bay Area native and a graduate of Swarthmore College and the Newhouse School at Syracuse University, Jackson makes his home in North Jersey. He grew up rooting for the Red Sox, Patriots, and Warriors, and he recently added the Devils to his sports fandom mosaic. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scott@wtfsports.org