May 26, 2025; Milwaukee, Wisconsin, USA; General view of a Boston Red Sox hat during warmups prior the game against the Milwaukee Brewers at American Family Field. Mandatory Credit: Jeff Hanisch-Imagn Images Jeff Hanisch-Imagn Images

Red Sox Star Predicted To Cash In With $182 Million Deal

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Oct 27, 2025 9:15 AM ET

The first order of business for the Boston Red Sox should be figuring out a way to keep Alex Bregman with the organization into the foreseeable future.

The partnership worked out so well in 2025, that even after one season it would be hard to see him go. Bregman's play on the field and veteran voice in the clubhouse held serious weight but now the club will have to decide whether that is enough to give him a large, new contract. The Athletic's Jim Bowden predicted Bregman to ink a six-year, $182 million deal this offseason.

"Bregman has an opt-out in his contract with the Red Sox and his camp has already indicated that he plans to test the free-agent market for a second straight offseason. He battled a quad injury for a good part of the 2025 season, and still managed to slash .273/.360/.462 with 28 doubles, 18 home runs and 62 RBIs in 495 plate appearances, though he was significantly less productive after returning from the IL (.727 OPS) than he had been before the injury (.927 OPS).

"Bregman was a leader in the Boston clubhouse by example and words, mentoring many of the Red Sox young future stars. He will be sought-after in free agency as the industry views him as a winning player who can contribute on both sides of the ball and perform on the biggest stage in the biggest moments. He’ll likely seek a long-term contract instead of settling for a shorter-term deal like he did last year. By opting out of his deal with the Red Sox, he’s walking away from a guaranteed $41.67 million in each of the next two seasons...Contract prediction: 6-years, $182 million."

The Red Sox should absolutely pay up to sign Alex Bregman

Bowden is an MLB insider and former general manager, so his words do hold weight around the league. This type of deal also arguably would be perfectly fair as well. If Bregman were not to opt out, he would have two years and $80 million left on his three-year, $120 million deal. An extension that essentially keeps those two years and adds roughly four years and $100 million should be fair.

Fellow Scott Boras client, Matt Chapman, signed a six-year, $151 million deal at a similar age to Bregman. If you do a deep dive into Chapman and Bregman's numbers, this value makes a lot of sense.

Throughout the season, the Red Sox's front office took every opportunity to openly talk about how much they love the third baseman. In September, Red Sox president and chief executive officer Sam Kennedy joined WEEI's "The Greg Hill Show" in September and told a story about a few of the team's leaders coming together with the front office to chart a path forward, and Bregman was included. Kennedy also said it would "take care of itself" and that Bregman's wants to be in Boston.

There will be competition for his services, but Boston should be all him at this price point. The price is fair in relation to Chapman's deal, there will be competition that likely will drive up the cost, and Boston clearly loves him. There's no reason to not pay him at this point.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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