Red Sox All-Star Has Most to Lose During Boston's Postseason Run

This Red Sox third baseman is not only playing for a ring in his first season with Boston.
Boston Red Sox third base Alex Bregman (2) hits an RBI double during the ninth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium.
Boston Red Sox third base Alex Bregman (2) hits an RBI double during the ninth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. | Brad Penner-Imagn Images

The MLB postseason is here. The Boston Red Sox's season has been filled with the highest of highs and lowest of lows, including trades, injuries, losing skids, and a 10-game winning streak that ultimately turned the season around.

After years of being content with mediocre rosters that would ultimately miss the playoffs, the Red Sox signed three players this past offseason that helped the team get back in the big dance: starting pitcher Garrett Crochet, reliever Aroldis Chapman, and third baseman Alex Bregman.

Crochet looked good, ending the year leading the majors in strikeouts, and he's since led the club to a 3-1 win over the New York Yankees in Game 1 of the American League Wild Card Series. Chapman, meanwhile, held down the closer role all season, posting a 1.17 ERA and 32 saves, tied for the fifth-most in the majors before signing a one-year deal earlier this month.

Then there's Bregman, who has struggled at the plate recently. In September, the three-time MLB All-Star has slashed just .216/.310/.330 and has been feeling under the weather (h/t @bradfo) leading up to the Red Sox wild card series. With a potential stop in free agency looming, any hiccups couldn't have happened at a worse time.

Red Sox 3B Alex Bregman Has Most to Lose This Postseason

Although he had two hits and an RBI in Game 1's 3-1 win over the Yankees, it's clear that Bregman still has the most to lose this fall.

Not only must Bregman replicate his Game 1 success to help the Red Sox win a World Series, but he needs more of the same if he wants to get paid this winter. MLB Trade Rumors' Steve Adams projected in August that Bregman could be looking for a $200 million contract, which teams — including Boston — might be hesitant to pay without a strong playoff run.

The Red Sox made a splash by signing Bregman to a three-year, $120 million contract, with opt-outs after this winter and in 2026. Although he lived up to his pricetag for the most part, Bregman's 48 missed games could leave the front office uncertain about what his next contract should look like.

When healthy, the 31-year-old gives the Boston lineup what it has lacked over the last few years: a strong, pull-heavy right-handed bat that can pepper the Green Monster. His performance this season earned him his third MLB All-Star nod, while also improving players around him in Trevor Story and Marcelo Mayer.

After struggling at the plate over the last month of the regular season, Bregman needs to continue his strong performance against the Yankees (and, hopefully, beyond) to get back in Red Sox fans' good graces. It will also help him earn more years and money on his next deal.

Bregman will have a decision to make whenever the Red Sox postseason wraps up, and the Texas native should have a plethora of teams trying to pry him away from Boston if he does opt out. His winning pedigree has certainly made an impact on the Red Sox from April to September, and he has to prove it again this postseason.

More Boston Red Sox News & Rumors: