In case you haven't heard, one of the top remaining free agents finally made a decision over the weekend. While plenty of people in the baseball world thought that third baseman Alex Bregman would wind up back with the Boston Red Sox, he opted for a five-year, $175 million contract with the Chicago Cubs.
The Cubbies came out of nowhere to snag the 31-year-old veteran in a surprising move, to say the least. While the rumors about the Philadelphia Phillies having any interest in Bregman died off long ago this offseason, the big get by Chicago could have a big impact on the Phillies' pursuit of Bo Bichette.
As everyone in Philadelphia knows by this point, the Phillies had a meeting with Bichette scheduled for Monday. Following the hiring of Don Mattingly as bench coach, it seems like Bichette's interest in joining the defending NL East champions is real.
After losing Alex Bregman, Red Sox going after Phillies' target Bo Bichette seems likely
With the Red Sox possibly hitting desperation mode after losing out on Bregman, will they set their sights on Bichette? They've previously been connected to the former Toronto Blue Jay this offseason. They'd be silly not to circle back now.
As The Boston Globe's Alex Speier reported, Red Sox chief baseball officer Craig Breslow has been looking to add a second middle-of-the-order bat (subscription required). Boston's first plan was Bregman. Their second plan? It could very well be Bichette.
According to Speier, multiple sources have characterized the Red Sox’s post-Bregman plans as being “creative” and “open-minded positionally.” That could mean anything is on the table for Breslow.
BO BICHETTE BELTS ONE TO DEEP CENTER 🤯@BLUEJAYS LEAD 3-0 IN GAME 7 pic.twitter.com/64ai0Udfyl
— MLB (@MLB) November 2, 2025
After making an "aggressive" offer to Bregman (that still fell short of the Cubs' deal), experts seem to think that Bichette will likely be the Red Sox's top target (subscription required), according to The Athletic's Jen McCaffrey.
Phillies' Bo Bichette pursuit has many moving parts
If the discussions go well with Bichette's camp, the Phillies could potentially add a career .294 hitter who has twice led the American League in hits. He would have probably made it a third time in 2025 if it hadn't been for a late-season injury.
That kind of consistency, with an innate ability to fight off bad pitches while looking for a mistake, would surely be a welcome addition to a Phillies lineup. It would bring an interesting wrinkle to an offense that has struggled to succeed in the postseason with an all-or-nothing mentality.
The Phillies may be forced to choose between adding the 27-year-old shortstop, who would likely play second base in Philly, and moving on from free agent catcher J.T. Realmuto. The veteran backstop has had since the MLB Winter Meetings to agree to the Phillies' current offer. His hesitation may cost him the opportunity to return after seven years in the City of Brotherly Love.
The Phillies would also be forced to move on from another player currently on the roster if they were to sign Bichette. They'd need to make room on the infield and they'd need to clear more payroll room. Third baseman Alec Bohm is the best bet, considering those two specifications. Heading into his final year before hitting free agency and earning $10.2 million, shipping him out makes the most sense.
However Monday's meeting turns out, now that Bregman is off the board the Phillies will be in a dogfight to secure Bichette's services.