You may have noticed that in recent years, teams seem more and more reluctant to fork over big, long contracts to even the most proven players. Despite speculation about longer-term offers, Alex Bregman signed only a three-year deal with opt-outs. Pete Alonso, Jack Flaherty, and many others got two years or less. 

One reason? Front offices hate getting stuck with underwater contracts. The longer the term, and the bigger the contract, the greater the chance you may get stuck with an albatross that you can’t move.

This offseason is a case in point: Despite their best efforts, the Cardinals could not find a taker for Nolan Arenado’s contract. Ditto the Yankees with Marcus Stroman, the Red Sox with Masataka Yoshida, and the Diamondbacks with Jordan Montgomery – those are just a few, and they’re not even the worst ones on the books.

So what are those? We keep a list of the most underwater contracts in baseball, in our Player Rankings section (which is always available to our GM-level subscribers). But some players near the top (or is it bottom?) of that list would still theoretically be tradeable because they still have plenty of field value – they’re just ridiculously overpaid, which means their current teams would have to eat a big chunk of money to move them. We’re talking guys like Mike Trout (who can’t stay healthy, but is still productive when he’s on the field), Manny Machado (who is still very productive, it’s just that his contract is heavily backloaded) and Giancarlo Stanton (who can still impact a lineup, even though he’s aging and overpaid).

The ones who are the most difficult to move are those players who offer little or no field value, and are still owed too much money. So even if the team kicked in a bunch of cash, it still wouldn’t be worth it. Better to just DFA these guys and call it a loss. Of that subset, here are the five worst:

 

 

Again, this is not a ranking of the most underwater contracts, as we’ve skipped over players, like Machado and Trout, who have more field value and are thus more playable, such that in theory a trade could still happen if their current teams ate a big chunk. The list above cherry-picks from that list to find the ones who offer little to no field value, and so are completely unmovable. They’re basically just sunk costs at this point. Let’s take a closer look at them.

 

Nick Castellanos

The Phillies have, per multiple reports, been trying to trade Castellanos all winter, but to no avail. He’s a replacement-level player now, heading into his age-33 season. And that’s because he’s unplayable in the field, so his only value is in his bat. And that’s been in decline for the past three years, with his WRC+ hovering around average, and his projections for 2025 also in the 100 range. It’s possible a team would take him as a DH if the Phillies ate the whole contract, though at this point in the offseason it seems like a longshot.

 

Andrew Benintendi

Notice how, in all the articles about the White Sox fire sale, few ever mention Benintendi? The team’s last trade chip is Luis Robert, Jr., and he’s coming off a terrible year. They don’t mention Benintendi because, frankly, he’s untradeable. He’s put up back-to-back years of -0.3 fWAR, with below-average offense (87 and 93 WRC+) and horrifying defense. He’s still owed $49.3M. Good luck shedding that contract, Chicago.

 

Javier Baez

Baez has put up only 2.1 fWAR in his three years in Detroit, providing below-average offense every year. His WRC+ has declined from 89 in 2022 to 63 in 2023 to a godawful 43 in 2024. Notably, after Baez’s latest injury kept him off the field, the Tigers went on a dramatic run without him, including a surprisingly deep playoff run. They’re better off without him than with him, as at this point his only value is as a defensive replacement. He’s still owed $73M for that.

 

Anthony Rendon

Rendon’s contract with the Angels is one of the worst in history, and given the recent news that he will miss the entire 2025 season due to hip surgery, it’s now in total-loss mode. We’ve also learned that the Angels did not insure the contract, so they have no financial recourse. In the last four years, he’s put up a total of 1.2 fWAR, while making an average annual salary of $38.5M. He’s owed that amount again in each of 2025 and 2026, but may never play again.

 

Kris Bryant

You thought Rendon’s contract was bad? Talk to the Rockies. They signed Bryant for $182M over seven years. In the first three of those, he put up -1.4 fWAR, with the last two being the worst. He has yet to play more than half a season in each of those, and his WRC+ has declined in the past two years from 75 to 70, along with poor defense. There’s just nothing left in the tank here, and the Rockies have him on the books for four more years and $108M. No wonder they haven’t signed anybody of note this year.