So many things happened around the Boston Red Sox over the last three days. They won the first game of the Wild Card series, then dropped two straight, losing the series 1-2 to the New York Yankees. For the first time, Alex Bregman lost a postseason series to the pinstripes. The Red Sox had also never lost to the Yankees in October since the Curse of the Bambino was broken in 2004. This kind of heartbreak often forces change, and for Alex Bregman, the future suddenly looks very interesting.

Bregman can opt out of his contract and become a free agent to test the market, leaving the final two years of his deal behind. The third baseman is widely expected to do just that after a fantastic season where he hit a solid .270/.360/.462  with an .821 OPS on his way to a third All-Star appearance. Plus, he established his role as a leader on the young team. And if such metrics are anything to go by, then he will likely seek a long-term deal. But the question is, will it be in Boston? Now, this is where it gets complicated.

The Red Sox might see things a little differently. MassLive’s Chris Cotillo suggested that Boston’s front office isn’t unified on bringing Bregman back. Cotillo wrote, “One of my big takes heading into this winter is that they might be more willing to let Bregman walk than everyone thinks.” Reason? Cotillo continued, “There are concerns about the aging curve and health there. Have to weigh that against leadership/intangibles/his ceiling. Remember, split camp last winter.”

This hesitation isn’t new. The front office was reportedly a split camp last winter, where Manager Alex Cora and CEO Sam Kennedy were huge supporters, but CBO Craig Breslow was more cautious. And now, Breslow’s concerns seem justified after Bregman’s performance dipped as he returned from a serious quad injury. The numbers add another layer.

Before the injury that had him sidelined for seven weeks, he hit .299 with 11 home runs, 35 RBIs, and a .938 OPS in 51 games. After returning on July 11, the 31-year-old hit .250 with seven homers, 27 RBIs, and a .724 OPS over his final 63 games, though his numbers declined in a major way over his final 35 games (.203 average, two homers, 10 RBIs and a .585 OPS after Aug. 17. Further, he earned a massive $40 million salary this season. But his .821 OPS would have ranked just 30th in baseball. That’s very good, but is it worth top-tier money? So, the question remains…

And when asked about his future, Bregman played his cards perfectly after the crushing loss. A reporter asked whether he could see himself staying in Boston. “Of course,” Bregman replied. “The future is bright. We envisioned winning tonight and making a deep run, but proud of the fight in the room… It was an honor to put on this jersey.” This kind of professional response kept the mystery alive and well. So, before canceling all the possibilities, we have to understand certain things.

The Tigers were Bregman’s most aggressive bidder last season, presenting a chance for him to reunite with A.J. Hinch, who managed him in Houston. They offered six years and $171.5 million with $40 million in deferrals and an opt-out clause after 2026, but since the two could not reach a common ground, that deal never materialized.

Even last winter, the Cubs also made a push for Bregman, offering him a four-year, $120 million deal with opt-outs after both the 2026 and ‘27 seasons. On the other hand, the Astros made Bregman a six-year, $156 million offer last winter, but Houston never budged off that number.

Keeping in mind that he has attracted such attention in the past, the same could be true for the current scenario as well. But why might his current club still make an effort to keep him?

Why Boston might still pay up

Despite the concerns, there are powerful reasons Boston might open up the checkbook. Even the reportedly cautious Craig Breslow has praised Bregman publicly all season long. He called extension talks “‘ongoing’ is always a fair summary.” He also stated, “He’s a guy we would like to have here in a Red Sox uniform for a long time.”

Then there’s the elephant in the room: the Rafael Devers trade. Bregman’s arrival indirectly led to the departure of the former third baseman. Allowing Bregman to walk away months later would be a public relations nightmare. And the fan base is already sensitive after losing Mookie Betts years ago.

But the Sox also have other players to worry about this winter. Shortstop Trevor Story has an opt-out after hitting 25 homers. Pitchers like Steven Matz and Dustin May are also free agents. Now, if Bregman hits the open market, he will command a huge price, and that will require a giant investment for Boston’s front office to consider.

Committing that much to Alex Bregman means they can’t spend it elsewhere. And Boston’s top priority is reportedly adding depth in rotation with high-end pitching after Garrett Crochet. And they could pursue free agents like Framber Valdez or Shane Bieber. So, the questions remain, and the roster equations become more and more complicated day after day. But it will be interesting to see where the superstar third baseman ends up for sure.