In 2025, the Boston Red Sox made the playoffs for the first time in four seasons and took big steps toward building the World Series contender the front office has worked on for half a decade. Some big spending from John Henry and Fenway Sports Group helped them get there, including a $120 million deal for Alex Bregman and long-term extensions for Garrett Crochet and Roman Anthony.
Of course, Bregman can opt out of the final two years of his deal this offseason, but if he opts in, the Red Sox's payroll will be close to the luxury tax threshold for 2026. Boston will start the season with $237-plus million on the books (figure courtesy of redsoxpayroll on Twitter), including Bregman and Trevor Story's contracts, and the first luxury tax threshold sits at $244 million.
There are some unsavory contracts contributing to the Red Sox's payroll total, however — not that funds or remaining under the luxury tax should matter for Henry, one of the richest owners in MLB. Offloading Rafael Devers freed up some money, but there are a handful of worse deals still on the roster (and one even came from the Devers trade).
3 contracts that could hold the Red Sox back in 2026 and beyond
Masataka Yoshida
Masataka Yoshida is a skilled hitter who's had his moments in a Red Sox uniform, but the lengthy contract to which Chaim Bloom signed him has been mostly not worth it. He signed a five-year, $90 million deal before the 2023 season, and he's posted just 303 games in the first three seasons of the contract.
Yoshida's bat also hasn't lived up tp the hype. He was an on-base machine in Nippon Professional Baseball, with a career .421 on-base percentage across seven seasons with the Orix Buffaloes. Yoshida can still put together a gutsy at-bat in MLB, but his .337 on-base percentage with the Red Sox leaves much to be desired.
Yoshida was one of the clutchest players on the Red Sox late in the 2025 season, but his frequent injuries, slow starts and underwhelming offense have made it hard to argue that his contract has been worth it.
Jordan Hicks
The Red Sox traded Devers' entire contract to the San Francisco Giants for an arguably worse one for Jordan Hicks. The Giants signed Hicks to a four-year, $44 million deal before the 2024 season, and it's no wonder they were so quick to get rid of it.
Hicks has posted a 4.41 ERA over 420.1 innings across his seven-year career, including 37 appearances as a starter. His first half-season with Boston went poorly and he severely struggled with his command. Hicks logged a 8.20 ERA with 15 strikeouts and 12 walks in 18.2 innings
Hicks has a blistering fastball in his arsenal and ranks in the 92nd percentile in fastball velocity. But such a pitch doesn't mean much if the pitcher has no command of it. Hicks is due $12.5 million in 202, and Boston would've been better off giving that money to Devers.
Kristian Campbell
Kristian Campbell took the minor leagues by storm in 2024, so much so that the Red Sox added him to their Opening Day roster and extended him on an eight-year, $60 million deal after just a few successful big league games. A month after his extension, Campbell started struggling, and never really found his way in the minor leagues.
Campbell batted .223/.319/.345 with 72 strikeouts over 68 games in the big leagues, a stark change from his 2024 breakout season, when he slashed .330/.439/.558 with a .997 OPS across three levels of the minor leagues. Boston sent Campbell down to Triple-A after his struggles in the big leagues, and he batted .273/.382/.417 over 73 games in Worcester. His infield defense was also disastrous, and he posted -9 outs above average and -16 defensive runs saved.
This is not to say that the Red Sox should give up on Campbell. In 2024, he showed an uncanny ability to put the bat on the ball, but the major leagues are an entirely different beast. Boston has begun extending young talent early in their big league careers to avoid anymore Mookie Betts and Xander Bogaerts situations, but there is a real risk of moving too fast and extending someone before their true skillset is realized. Campbell still has plenty of time to prove himself, but it would be nice if the Red Sox didn't owe him $2.25 million next year.