Red Sox’s Most Problematic Contract Shouldn’t Surprise Anyone

The Boston Red Sox have hit a few home runs over the last few years from a contract perspective.

If you look at the organization right now, Boston was able to get early extensions done with Roman Anthony, Ceddanne Rafaela, Brayan Bello, Garrett Crochet, Garrett Whitlock and Kristian Campbell. Boston handed out a good deal this past offseason as it signed Ranger Suárez to a five-year deal in free agency. The club has a handful of core pieces under team control for the foreseeable future as well, like Jarren Duran, Johan Oviedo, Marcelo Mayer, Triston Casas, Caleb Durbin, Carlos Narváez, Payton Tolle and Connelly Early, among others.

All of this is to say that the Red Sox are in a very good position for the 2026 season and beyond. But every team has some sort of contract miss. Bleacher Report's Tim Kelly broke down the worst contract for each team and for Boston, that was Masataka Yoshida's five-year, $90 million deal.

Not Boston's best contract

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox outfielder Masataka Yoshida (7) hits a two run RBI during the seventh inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

"Boston Red Sox: Masataka Yoshida," Kelly wrote. "Original Contract: Five years, $90 million. Remaining Money: $37.2 million through 2027. While Masataka Yoshida has gotten strong results in the World Baseball Classic for Japan, it's fair to say that he's been a bust to this point in his MLB career. Over his first three MLB seasons, Yoshida has been worth just 1.5 WAR total, per FanGraphs. Since posting minus-four defensive runs saved and minus-eight outs above average in left field during his rookie season, the Red Sox have treated Yoshida like a DH, as he's played just 45 innings in the outfield over the last two seasons.

"Yoshida is an obvious change of scenery candidate for a Red Sox team that has a surplus of outfielders, and will likely use Jarren Duran as their primary DH to open the season. The two choices chief baseball officer Craig Breslow has right now are to keep Yoshida as an expensive bench player or subsidize a trade for a minimal return."

Yoshida's contract has been talked about endlessly because there are two years left on it, but he doesn't currently have a pathway to playing time with Boston right now. That doesn't mean he's not a talented player, though. Look at the World Baseball Classic, for example. He has been electric for Team Japan. For the Red Sox, they are fortunate to have the best overall outfield in baseball. He isn't great defensively, but his contract wouldn't look as bad as it does if he had a clear pathway to playing time.

He can really hit. In 2023, he slashed .289/.338/.445 with 15 homers and 72 RBIs in 140 games played as a rookie in the majors. Since then, he has dealt with ever-changing roles and injuries. If the Red Sox end up finding a trade partner for him at some point, this deal is not going to look as bad as it does because he has plenty in the tank.