Eating Dead Money for Fun and (Negative) Profit

The Red Sox have a recent history of releasing or trading players and paying a significant portion of their salaries. John Henry has apparently had enough.

Teams make bad deals. This is not news. Theo Epstein, maybe the greatest executive in the history of the game, has made bad deals. We all remember Matt Clement, Eric Gagne, Mike Cameron, and Carl Crawford. Fortunately, salaries had not exploded back then.

Dead money is what happens when a team says “Oops, we don’t want this guy anymore, but we still owe him money.” This is major league baseball. All contracts are guaranteed. The only options are releasing the player outright (DFA) or trading him. In either case, you will still owe the portion of his salary that his new club doesn’t pick up.

There is a business term for this: sunk cost. When you sign a multi-year deal, you have essentially already spent the money. This is how John Henry looks at it. When he spends money on an asset, he expects that asset to produce revenue, in this case a good player who puts butts in seats and sells beer, hot dogs, and merch.

Ben Cherington took over as general manager in 2012. After a disastrous first season thanks to Larry Lucchino’s hiring of Bobby Valentine, he went to work in the 2013 offseason and added some solid players such as Mike Napoli, Shane Victorino, and Jonny Gomes. These relatively low-cost players led the Red Sox to World Series in 2013. After a pretty bad 71-win 2014, Ben decided to go for broke. He signed Hanley Ramirez to a 4 year, $88M contract and Pablo Sandoval to a 5 year, $90M contract within 2 days in November of 2014.

Hanley Ramirez was nowhere near the player he was with the Marlins, and Sandoval was a shadow of his former self with the Giants (although he did now cast a much bigger shadow). Enter Dave Dombrowski in 2015. He wanted to build a championship roster, and he knew these guys would not be a part of it. He DFA’d Sandoval in July of 2017 and Ramirez in May of 2018. The Red Sox ended up eating $15M of Ramirez’ salary and $45M of Sandoval’s salary.

JOHN HENRY DEAD MONEY TRACKER: $60M

Dombrowski made some big moves of his own. He signed David Price to one of the largest contracts in MLB history in December of 2015, 7 years, $217M. Price had an up and down stint with the Red Sox, and he pissed off a lot of people, but he did start the clinching game of the 2018 World Series. He ended up being a member of the Chaim Bloom Salary Dump of 2020 when he was traded to the Dodgers with Mookie Betts. While technically a salary dump, the Red Sox had to eat $48M of the $96M left on his deal.

JOHN HENRY DEAD MONEY TRACKER: $108M

Following the 2018 season, Dombrowski gave another World Series hero, Chris Sale, a contract extension of 5 years, $145M. Sale was a great pitcher for the Red Sox, but his injury problems had just started. When Craig Breslow took over in 2023, he traded Sale to the Braves and ate $17M of the $28M left on his deal. Sale went on to win the Cy Young in 2024.

JOHN HENRY DEAD MONEY TRACKER: $136M

Many people think John Henry didn’t allow Chaim Bloom to spend money, but he did allow Bloom to make two big free agent signings. He signed Trevor Story to a 6 year, $140M contract in 2022 and Masataka Yoshida to a 5 year, $90M contract in 2023. Story has been hurt for all seasons except 2025, when he was a viable big-league starter (.717 OPS overall with the Red Sox). Yoshida’s star quality in Japan has not translated to MLB as Bloom expected (.762 OPS).

Trevor Story will be the Red Sox starting shortstop, but his position is precarious. He is no longer a good big-league SS. He is still injury prone. He is not a $25M per year player. Yoshida will most likely not be a starter for the Red Sox, and if they can’t move him, could be a bench player. Story has $50M left on his contract and Yoshida $36M.

JOHN HENRY DEAD MONEY TRACKER: $222M?

Not so fast. I think another $86M is a bridge too far for John. I think he’s done seeing his money go down the toilet. They won’t move Story because they don’t have depth in the infield, especially since Romy Gonzalez’ future is uncertain. It’s the opposite in the outfield. With Rafaela, Abreu, Anthony, and Duran, they have an everyday starting OF and an everyday (possibly rotating) DH. There is no room for Yoshida, not even as a platoon player since he is left-handed. He is a bad outfielder and a bad baserunner to boot.

Will he be traded? Maybe. If Breslow can find an out-of-town stupid general manager that is impressed with Yoshida’s performance in the World Baseball Classic, he may have a deal, but I doubt anyone will take on his $18M salary for two years, and the chances of John Henry eating any part of that? Slim and none. So, this is a big test for Craig Breslow. Does he have the savvy to work a deal or the cajónes to DFA Yoshida? I think you know the answer to that.