How does Alonso deal affect Red Sox's pursuit of Bregman?

December 10th, 2025

ORLANDO, Fla. -- The thought of towering slugger Pete Alonso taking aim at Fenway Park’s Green Monster was an enticing possibility, one that was discussed for weeks. But on Wednesday, the final day of the Winter Meetings, the Red Sox learned that the right-handed hitter is headed to the Orioles on a five-year, $155 million contract, sources told MLB.com.

While it’s always unpredictable which free agents will end up where, the fit between Alonso and the Red Sox felt too perfect for it not to happen. Chief baseball officer Craig Breslow has spoken all winter about the need to acquire a slugger who could sit in the middle of Boston’s batting order.

“Without getting into the details of specific pursuits, the profile that I've talked about wanting to add is certainly one that he would fit,” said Breslow. “But these things don't always line up. We’ve got to make the best decisions that we can for the organization. And players have to make the best decisions for themselves and their families, and now we've got to figure out another way to improve our roster.”

Alonso and Kyle Schwarber were the two best home run hitters available via free agency, and Schwarber agreed to a five-year deal with the Phillies on Tuesday. That one didn’t sting as much to Red Sox Nation because Schwarber is a left-handed hitter, and there was a sense of inevitability he would wind up back in Philadelphia, where he is beloved.

Now, all eyes turn to Breslow, and how he pivots to put some more production into his batting order.

The first domino effect is that this would seem to increase the chances Boston will retain veteran leader , who exercised the opt-out in the three-year, $120-million deal he signed in February.

“We remain engaged with any player that we think can help us,” said Breslow. “He’s certainly one of them.”

Though Bregman hasn’t really fit the slugger profile since he mashed 41 homers for the 2019 Astros, he remains an invaluable player due to his hitting, defense and tireless work ethic, which he spreads around the clubhouse to his teammates.

Even before Alonso slipped away, reports surfaced that Boston’s top goal this offseason is securing a new deal with Bregman. Now, they could have more financial freedom to do so.

“In terms of Alex, we saw what he was able to bring on the field and in the clubhouse last year,” said Breslow. “He's still out there, and he's a guy that could fit our roster particularly well.”

In February, the Sox were willing to go high on AAV with Bregman (though a chunk of his $40 million per year salary was deferred) but were conservative with years.

To get him back, Boston figures to, at the very minimum, offer a five-year contract that could come in at a similar dollar amount to the deals that Alonso and Schwarber signed the last couple of days.

The Red Sox have already improved their pitching this offseason by trading for Sonny Gray and Johan Oviedo.

If Bregman comes back, he would again be a veteran presence and a right-handed bat to complement the team’s strong core of left-handed hitters that includes Roman Anthony, Wilyer Abreu and Jarren Duran. Trevor Story’s right-handed bat is also back in the fold after a resurgent season.

But the Sox would likely need to get another hitter to go with Bregman, one who can belt the ball out of the ballpark.

Bo Bichette is a free agent who might be linked to the Red Sox even more now that Alonso is out of the picture. Though the shortstop’s career high in homers is 29 in the ‘21 season, Fenway’s friendly left-field dimensions could allow him to crack 30 for the first time in his career.

With Story entrenched as Boston’s shortstop, Bichette would likely make a position switch if he came to the Red Sox, either to second or third base.

Bichette is still in his prime at 27 years old, and his move to the Red Sox would be a feel-good story. His parents met at a gym behind the Green Monster. Dante Bichette, Bo’s dad, played two seasons in Boston at the end of his career.

Other power hitters available via free agency include Jorge Polanco and Eugenio Suárez.

“I still feel like adding some slug into the lineup is a really good place to start,” Breslow said. “That said, if we set our sights on only one or two options, and those fall through, we can't [lack] alternatives. So we've got to figure out a way to round out the roster, to improve the offense, and that's what we're set on right now. If that ends up looking a little bit different, I think we have to be open to it.”

There’s also the possibility of a trade. The Red Sox’s strong depth both in starting pitching and in the outfield could help a deal happen, not to mention an emerging farm system.

“We’ve had [trade] conversations ongoing for a couple of months at this point,” said Breslow. “To date, there haven't been a ton of really significant trades. It's impossible to know where that will end up, but we’ll remain engaged in both free agency and with other teams.”