Craig Breslow’s vision is to build a “winning team.” When you look at how the Red Sox are exploring options this offseason, that much is clear, especially around the decision whether to re-sign their All-Star third baseman. The front office hasn’t closed the door, but they haven’t flung it wide open either. Meanwhile, Alex Bregman isn’t sitting idle. He’s making things interesting, reportedly eyeing other clubs as leverage builds on both sides.

Bregman entered free agency after opting out of his contract following a strong 2025 campaign with Boston. He posted a .273/.360/.462 slash line with 18 home runs in 114 games, earning his first All-Star selection since 2019. The 31-year-old proved his value despite missing seven weeks with a quad injury. Now the question becomes whether the Red Sox will meet his asking price or if another team swoops in to land the veteran infielder.

The back-and-forth has turned into something of a chess match. An update posted recently on X captured the dynamic perfectly. It wrote, “Red Sox will leak that they’re exploring all these other options / that they can only afford one bat. Bregman’s camp will leak that he’s gonna get $175M from someone. In the end, all roads will lead him back where he belongs. These two parties need each other.”

These are the mind games playing out behind those closed doors as both sides try to gain the upper hand.

What makes this dance more intriguing is the production Bregman delivered in his lone season with the Red Sox. Beyond the numbers, he brought veteran leadership to a young clubhouse and defensive reliability at third base.

This summer, Boston reached the postseason for the first time since 2021. That kind of impact doesn’t show up in a box score, but it matters when you’re trying to build a winning roster.

Through it all, manager Alex Cora has made his position clear. He’s placing his trust in Breslow to navigate this critical offseason. “He did an amazing job last year. I know a lot of people don’t give him credit, but if you look at the offseason we had last year — Aroldis Chapman, Justin Wilson, Alex Bregman, Garrett Crochet — three All-Stars, Wilson was great,” Cora said, speaking about the job his chief baseball officer did last winter.

“Let him be, let him do the job. Obviously, he will ask me how I see it, but at the end of the day, we make decisions based on what we have to improve on our 40-man roster and our 26-man roster, and hopefully we can do that.”

Both sides have valid points. Bregman took a risk with a shorter contract, and his bounce-back season has put him in a position to seek a longer deal around a five-year, $175 million contract. Meanwhile, the Red Sox are focusing on finding a balance with their need for top-tier pitching and a power bat under a budget.

Breslow addressed the Alex Bregman situation after the GM meetings. He said, “We recognize what he has done for us. We also recognize what he could potentially do for us. Now we’ve got to evaluate how we best improve our roster in 2026, and we’ll be very open-minded about what that could look like.”

While negotiations with Bregman continue, Boston is already exploring alternatives to strengthen its lineup.

The Red Sox’s plan B: Targeting big bats beyond Bregman

The Red Sox are reportedly keen on Bo Bichette, a free-agent infielder known for his hitting prowess. He’d be a good fit at either third or second base. Their involvement suggests they’re not counting on Bregman returning anytime soon, and they’re already making contingency plans.

Boston’s name has also been floated in connection with Kyle Schwarber. He’s a former Red Sox player, a slugger who blasted 56 home runs in 2025, and boasted an impressive on-base power metric. He’s a potential power bat if the front management decides to move on from Alex Bregman’s contract.

Another key player to watch is Pete Alonso, the Mets’ right-handed power hitter. Reports indicate the Red Sox might lean towards acquiring Alonso over Schwarber. The reasoning? Alonso’s playing style aligns better with Fenway Park’s dimensions, and he wouldn’t be tied to a qualifying offer.

Essentially, the front office is signaling, ‘We’re considering a return for Bregman, but we’re also prepared for his departure.’ By pursuing Bichette, Schwarber, and Alonso, they’re boosting their bargaining position. This signals they have alternative strategies prepared, should the $175 million negotiations falter in Boston.