Bregman joined the Red Sox in a blockbuster move during the offseason. He joined Rafael Devers and Jarren Duran as Boston’s stars in the field. After a .500 season in 2024, the team was under pressure to add a star and re-enter the ranks of contenders in the AL. Bringing Bregman in accomplished that goal if the Red Sox can hold on to their Wild Card spot for the rest of the season.

Boston’s focus is on making the playoffs and going on a run. However, the front office cannot afford to have that excitement distract it from securing the roster long-term. One of the biggest pieces of that puzzle is Bregman, who signed a unique contract. The former All-Star has the option to decline the rest of his deal in the 2025 and 2026 offseason if he decides to move on.

Bregman’s original contract was for three years, totaling $120 million. However, he was coming off an underwhelming season in 2024, preventing him from getting a top-of-the-market deal. After putting together a bounce back year at the plate and in the field, Bregman could potentially set the third baseman market with a new deal this winter. Even at 31 years old, he is valuable.

If the Red Sox win a couple of series in October, Bregman could accept his option or negotiate a new deal with Boston. However, an early exit could cause him to consider his other options and listen to other offers.

If he is available, Bregman will have plenty of suitors

When the Houston Astros moved on from Bregman, plenty of teams were interested. The former All-Star is no longer the best third baseman in the league, but he is not very far off. The fact that he is back to his normal self this season puts him near the top of many general managers’ target list heading into the offseason. As soon as Bregman declines his option, the phone will ring.

Bregman has not said much about the contract talks between his agent and the Red Sox. While some experts believe that he fits best in Boston, the team may wait until the playoffs end before making its choice. The veteran has spent time on Cora’s injured list this season, creating concern about reoccurring injuries that could impact his production as his career continues.

Bregman’s numbers are as good as they have ever been. Slashing .279/.363/.482 at the plate, the veteran has been a great leader for his team, both on the field and in the clubhouse. Young players like Mayer need guidance as they transition into the major leagues, and Bregman has taken to that role perfectly. The real question is how much the Red Sox value that trait.

There is a world where the Red Sox go home early and are desperate to keep Bregman around. However, an exit in the Wild Card round would introduce a new level of drama for Cora and the front office to deal with. The third baseman’s name was thrown around a bit at the trade deadline. However, the Red Sox quickly doused that spark before it became anything serious.

That kind of move likely means that Boston wants to retain him. What the team needs to figure out is whether or not he fits into its long-term plans.

Keeping Bregman could prevent the development of Boston’s young talent

Bregman has been supportive of the Red Sox’s young talent throughout the season. However, he and Trevor Story aren’t exactly in the primes of their careers anymore. Story’s production has fallen off, even if his infield teammate continues to rake at the plate. Despite their bright moments, Cora and Boston could decide that developing Mayer and Cedanne Rafaela is more important.

Mayer entered the big leagues with a lot of hype. While Boston has sent the young prospect back to the minor leagues, he showed flashes with the Red Sox. The organization is excited for the team’s future with him, Roman Anthony, and Kristian Campbell leading the way at the plate. If all three of them blossom into stars, Bregman becomes the odd man out at third base.

If Boston succeeds this fall without Bregman leading the way, the team could decide he is not worth negotiating a new deal with. It would please the front office if the veteran accepted his option, but that is very unlikely. For Bregman, playing well in the playoffs and leading a deep run could help him get a big payday in free agency, even if it does not come from the Red Sox.