Red Sox Winners, Losers From Jake Bauers Deal, Including Triston Casas

The Boston Red Sox made a big splash on Friday afternoon.

Aug 22, 2026; Milwaukee, Wisconsin, USA; Milwaukee Brewers right fielder Jake Bauers (9) is greeted in the dugout after hitting a two run home run against the Atlanta Braves at American Family Field. Mandatory Credit: Benny Sieu-Imagn Images | IMAGN IMAGES via Reuters Connect

The Boston Red Sox got their guy on Friday.

Rather than waiting around to strike and make a deal, Boston swung the first major deal of the offseason in free agency by agreeing to terms on a four-year, $58 million deal with slugger Jake Bauers. Boston entered the offseason needing more offense and immediately filled a major hole. With Bauers, the Red Sox are getting a left-handed slugger coming off a season in which he hit 26 home runs, drove in 86 runs and won the 2026 National League Championship Series Most Valuable Player Award.

With that being said, here are the biggest winners — and losers — from Boston's deal with Bauers.

Winners

Milwaukee Brewers first baseman Jake Bauers (9) after tagging out Tampa Bay Rays right fielder Ryan Vilade at first during Game 5 of the World Series at Tropicana Field in St. Petersburg, Fla. on Oct 28, 2026. | USA TODAY Network via Reuters Connect

Jake Bauers

Let's start with the obvious one here. Bauers had a phenomenal 2026 season and just parlayed it into a significant payday. In 2026, he made $2.7 million in his final campaign as a member of the Milwaukee Brewers. Overall, he has made just over $9.4 million in his professional career, per Spotrac. He's going to make more than that in 2027 alone. Bauers had a great season and now he's joining another World Series contender where he will have a big role and make a lot of money. It's hard to ask for much more.

Craig Breslow

Breslow is cooking so far this offseason. He said all of the right things at the General Manager Meetings, had his title changed to president of baseball operations and now he has plugged a significant roster hole before anyone else could strike and set the market. Boston clearly is being aggressive and that's for the best. Breslow is off to the races.

Red Sox's Lineup In General

The Red Sox finished the 2026 season 26th in the league with 163 homers as a team. Right away, they've struck and added a guy coming off a 26-homer season to bolster the designated hitter spot and serve as a backup first baseman. A great move and a great start to the offseason in general.

Losers

Apr 29, 2025; Toronto, Ontario, CAN; Boston Red Sox first baseman Triston Casas (36) hits a single against the Toronto Blue Jays during the eighth inning at Rogers Centre. Mandatory Credit: John E. Sokolowski-Imagn Images | IMAGN IMAGES via Reuters Connect

Triston Casas

Casas is working his way back still and there's a real chance he actually gets into winter league action. But with Willson Contreras and Bauers now on the roster, it's hard to see much of a path for Casas to significant big league playing time, barring an injury. Contreras will be at first base and Bauers likely as the DH. Bauers just inked a four-year deal and Contreras has a 2028 club option that very well could end up being picked up. The path isn't great for Casas.

Jarren Duran/Masataka Yoshida

There have been rumors all offseason already about Duran potentially being on the move. With Bauers coming to town and likely serving as the DH on a consistent basis, that means that an outfielder will not. The Red Sox got through the outfield logjam — when everyone was healthy — by rotating them as DHs. Bauers appears likely to man the spot on a consistent basis. That isn't great for Duran — or Yoshida's — standing on the team.