Inside The Red Sox

NL Team Emerges As Red Sox's Top Competition For Alex Bregman, Bo Bichette

Will the two teams simply split the pot?
Aug 19, 2025; Pittsburgh, Pennsylvania, USA;  Toronto Blue Jays shortstop Bo Bichette (11) in the batting cage before the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images
Aug 19, 2025; Pittsburgh, Pennsylvania, USA; Toronto Blue Jays shortstop Bo Bichette (11) in the batting cage before the game against the Pittsburgh Pirates at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

Alex Bregman has multiple suitors. Bo Bichette has multiple suitors. But there aren't a lot of instances of crossover.

For Bregman, the Boston Red Sox's incumbent third baseman, the Toronto Blue Jays appeared to drop out of the mix recently, and it even seems fairly unlikely now that the Blue Jays will bring back Bichette, who has been in the organization since he was drafted in 2016.

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It seemed previously like the Blue Jays could be the main team pushing the Red Sox for both Bichette and Bregman. Now, it appears that distinction has fallen to a National League contender instead.

Cubs in on both Bregman and Bichette

According to a Wednesday report from Ken Rosenthal and Will Sammon, the Chicago Cubs have an interest in both Bregman and Bichette, due to their desire to upgrade at third base over the production they got from rookie Matt Shaw this past season.

"Another reason for the logjam in free agency might be the reluctance of certain players to sign before others they are competing with in the market – a dynamic possibly in play with ... Bregman and Bichette," the insiders wrote.

"Bregman, who turns 32 in March, is four years older than Bichette, but a number of teams view his leadership as a difference-maker. The Boston Red Sox and Chicago Cubs are among the teams talking to both players, according to people briefed on the conversations. The Blue Jays have been in touch with both, too, but now appear more focused on (Kyle) Tucker."

Bregman is a cleaner fit for the Cubs since he's played third base for the vast majority of his career, and we know the Red Sox prefer Bregman too, since they've already had him. The Cubs being in on both could create a doomsday scenario in which Boston loses Bregman to Chicago, then has to contend with big-market teams like Toronto and the Philadelphia Phillies for Bichette.

We also know, though, that the Red Sox blew the Cubs' offer for Bregman out of the water last year. And Chicago also might have to swing a trade for second baseman Nico Hoerner, who is a fantastic player, to make all the puzzle pieces fit together.

In conclusion, while the Red Sox should absolutely view the Cubs as a threat at this point, they also should feel embarrassed if they wind up with neither of these two star free agents while Chicago gets one.

More MLB: Dominoes Beginning To Fall In Red Sox-Alex Bregman Saga


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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