Each MLB Team's Nightmare Contract By 2027
With most Major League Baseball teams already in offseason mode and the free-agency signing window opening in less than a month, it's a good time for a reminder that long-term contracts are like a box of chocolates.
You never know what sort of ROI you're gonna get.
If we include (which we did) the deferred/retained payments Miami and Washington owe to Giancarlo Stanton and Stephen Strasburg, each of the 30 teams has multiple players signed through at least 2027.
And for each of the 30 teams, we've identified the current contract that figures to be most painful for them next offseason. In most cases, it's also the most painful right now.
Teams are broken up by division and listed in alphabetical order by location. All contract data courtesy of Spotrac. The age in each player's "Age/Contract" section is as of Opening Day 2026.
American League East
1 of 6
Baltimore Orioles: Tyler O'Neill, RF
Age/Contract: 30, $16.5M player option for 2026, $16.5M in 2027
Baltimore's actual nightmare situation is that 2027 is the final season before Adley Rutschman reaches free agency, as well as the O's next-to-last year of team control on Gunnar Henderson.
Dean Kremer, Tyler Wells and Kyle Bradish are also fast approaching free agency as the window on this nucleus that won 101 games two years ago is already closing.
However, that three-year, $49.5 million deal with O'Neill is looking mighty ugly after he hit .199 in 54 games played in 2025. Enjoy those Opening Day homers, though.
Boston Red Sox: Masataka Yoshida, DH
Age/Contract: 32, $18.6M in 2026, $18.6M in 2027
With four young, talented outfielders each under team control through at least 2028, Boston may well be looking to unload an expendable Yoshida this offseason.
And if that's the plan, at least he hit .333 in September before also going 4-for-7 at the dish in the wild card round loss to the Yankees.
Might be able to find a taker for the two years and more than $37 million left on his deal.
New York Yankees: Ryan McMahon, 3B
Age/Contract: 31, $16M in 2026, $16M in 2027
The figure of $16 million is kind of whatever to the Yankees. At any rate, similar salaries didn't stop them from kicking both Marcus Stroman and DJ LeMahieu to the curb this summer.
However, the Yankees have already borne witness to the fact that McMahon isn't the same hitter outside of Coors Field, where he had a career OPS of .817. He posted a .641 mark in the 54 games after New York acquired him, pretty much only providing value with his glove.
Tampa Bay Rays: Yandy Díaz, 1B/DH
Age/Contract: 34, $12M in 2026, $13M in 2027 (if he reaches 500 PA in 2026)
If Díaz's option doesn't vest, Tampa Bay's only figure currently on the books for two seasons from now is a club option on Drew Rasmussen—exact amount to be determined by 2026 escalators, but they can decline it for $500,000.
The Rays also might look to trade Díaz this winter, given Jonathan Aranda's breakout season at first base that relegated Díaz to mostly DH duties.
In other words, there really isn't a nightmare contract here, which is pretty well business as usual.
Toronto Blue Jays: Andrés Giménez, 2B
Age/Contract: 27, $15.6M in 2026, $23.6M annually from 2027-29, $20M club option (or $2.5M buyout) in 2030
While Tampa Bay has no real candidates for this list, Toronto has a few too many.
The Anthony Santander signing isn't looking great, and José Berríos's two-year, $48 million player option for 2027-28 is a large-looming variable. But owing Giménez $73.2 million from 2027-29 takes the cake.
That's an awful lot of money for a plus glove who had a sub-.600 OPS this season, and having that much earmarked for this middle infielder could end up being the biggest reason the Jays fail to re-sign their other one this winter: Bo Bichette.
American League Central
2 of 6
Chicago White Sox: Andrew Benintendi, LF
Age/Contract: 31, $17.1M in 2026, $15.1M in 2027
Benintendi hit 20 home runs for a second consecutive year and was more valuable for the White Sox than in either of his previous seasons on the roster.
However, we're talking a season of 0.2 fWAR after back-to-back years in the negatives. So, not a ringing endorsement for the two years and $32.2 million left on his deal.
He's also the only choice from the White Sox, aside from the pair of $20 million club options they have for Luis Robert Jr. in 2026 and 2027.
Cleveland Guardians: Steven Kwan, LF
Age/Contract: 28, arbitration-eligible in 2026 and 2027
This one isn't a nightmare for financial reasons, but rather expiring reasons.
Kwan was the only outfielder who amounted to anything for Cleveland in 2025, and his free-agency clock is already ticking so loudly that he was one of the most frequently mentioned names ahead of this summer's trade deadline.
Will he still be on the roster in 2027? Maybe with an extension in place?
Detroit Tigers: Javier Báez, SS
Age/Contract: 33, $24M in each of 2026 and 2027
Báez was an All-Star this year for the first time since 2019, but what was an .809 OPS through 80 team games gave way to a .527 mark for the rest of the regular season.
This didn't look too bad in June, but the Tigers can't exactly be thrilled with how much they still owe this free swinger who served as a utilityman in 2025.
Kansas City Royals: Seth Lugo, RHP
Age/Contract: 36, $21.5M in each of 2026 and 2027, $17M club option (or $3M buyout) that becomes a guaranteed $20M if he reaches an innings pitched minimum
Like Kwan in Cleveland, Lugo featured prominently on the various "trade deadline big boards" up until the Royals gave him this two-year, $46 million extension in late July.
It aged disastrously, though, with Lugo supplying an 8.35 ERA over his next seven starts before missing all of September with a lower back strain.
He turns 36 in November, and Kansas City has its fingers crossed that he still has a couple solid years left in the tank.
Minnesota Twins: Byron Buxton, CF
Age/Contract: 32, $15.1M in each of 2026, 2027 and 2028
Buxton had a career-best run through 2025, joining Juan Soto and Shohei Ohtani as the only players with at least 35 home runs and 20 stolen bases.
However, even in his much healthier than usual All-Star campaign, he still missed 36 games and remains one of MLB's preeminent "if he stays healthy" players. (Just about any team would gladly sign on for this potential nightmare contract, though. If Buxton was a free agent this winter, he'd haul in a whole lot more than 3/$45.3 million.)
American League West
3 of 6
Athletics: Luis Severino, RHP
Age/Contract: 32, $25M in 2026, $22M player option in 2027
This isn't a terrible contract, and Severino might opt out of that last year just to get the heck out of Sutter Health Park, given his 6.01 ERA at home and 3.02 ERA on the road in 2025.
However, it's one of only three options on the A's ledger, and the long-term deals with Brent Rooker and Lawrence Butler both look solid.
Houston Astros: Jose Altuve, 2B/LF
Age/Contract: 35, $33M in each of 2026 and 2027, $13M in each of 2028 and 2029
After a brutal first 47 games of the 2025 campaign, Altuve rallied for 22 home runs and an .836 OPS the rest of the way. Still, with a declining batting average and deteriorating defense, it was the least valuable (aside from 2020) season of his career.
That's not a great look in the first year of his five-year extension.
Los Angeles Angels: Mike Trout, RF/DH
Age/Contract: 34, $37.1M in each of 2026-30
At least Trout used to mash while acquiring the "injury prone" label, slugging .630 while missing more than 30 percent of Angels games from 2017-22.
Over the past three seasons, though, he has slugged .470, turning into a wildly overpriced version of Jake Burger.
His contract is nowhere near Anthony Rendon or Stephen Strasburg levels of pain, but we may have officially crossed the threshold where the amount left on Trout's deal (over $185 million) is an albatross.
Seattle Mariners: Luis Castillo, RHP
Age/Contract: 33, $24.15M in each of 2026 and 2027, $25M in 2028
It's not until after 2028 that the Mariners have to decide what they're going to do about Julio Rodríguez's gigantic option for 2030-37.
In the meantime, their nightmare might be Castillo, who is still slated to be Seattle's highest-paid player for the next three years, even though he might only be their fourth-best starting pitcher at this point, let alone two years from now.
Texas Rangers: Marcus Semien, 2B
Age/Contract: 35, $26M in each of 2026 and 2027, $20M in 2028
Take your pick from what will practically be a retirement home for aging veterans in Arlington two years from now.
Jacob deGrom will be making $37 million in his age-39 season; Nathan Eovaldi $24 million at age 37. And though Corey Seager will only be in his age-33 year, it's an old 33, given his injury history and the physical demands of a career spent at shortstop.
Semien figures to be the biggest problem, though, already 35 and posting a sub-.700 OPS in each of the past two seasons.
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National League East
4 of 6
Atlanta Braves: Austin Riley, 3B
Age/Contract: 29, $22M annually from 2026-32, $20M club option for 2023
The first season (2023) of Riley's 10-year, $212 million extension went pretty great. The second and third seasons were less encouraging, missing 112 games and posting a combined OPS (.760) more than 100 points below where he had finished each of the previous three years.
Only seven years to go?
Miami Marlins: Giancarlo Stanton, DH
Age/Contract: 36, $10M deferred annual payments from 2026-28
Aside from these upcoming deferred payments to the former NL MVP, Miami's only known salary figures for 2026 and beyond are the $17.3 million owed to Sandy Alcantara next season and the $21 million club option they have on him for 2027.
It will be interesting to see if they get pressured by the MLBPA to spend some money this offseason after ending up with a payroll more than $10 million below even the A's and White Sox.
New York Mets: Brandon Nimmo, OF
Age/Contract: 33, $20.5M annually from 2026-30
The first three seasons of Nimmo's eight-year, $162 million deal have been respectable enough, worth a bit better than 3.0 WAR on average. But here come the years that made the sheer length of that contract a big surprise to many when it was signed.
Nimmo has already transitioned from full-time CF duties to basically a full-time LF, and he has a .744 OPS over the past two years compared to an .828 mark in his ages 27-30 seasons.
For New York's sake, here's hoping Nimmo's next five years don't wind up being on par with Starling Marte's past three seasons.
Philadelphia Phillies: Aaron Nola, RHP
Age/Contract: 32, $24.6M annually from 2026-30
Sidelined by injury for the first time in nearly a decade, Nola was a shell of his former self in 2025. He had a 6.16 ERA in nine starts before missing three months of action, and returned with a 5.84 ERA over his other eight starts of the season.
Can he rebound for 2026 and beyond, or is his even-year magic no more?
Washington Nationals: Stephen Strasburg, RHP
Age/Contract: 37, $23.57M retained in 2026, $26.7M deferred in each of 2027 and 2028, $30.7M deferred in 2029
Well, if we're counting deferred payments to Stanton, better also count the deferred payments to Strasburg. (For what it's worth, the Nationals also still owe Max Scherzer $15 million in each of 2026 and 2027.)
It was either this retired former ace or Keibert Ruiz, who is slated to make $36.875 million over the course of the next five seasons. That's barely $7 million per year, though, and at least he might actually provide some value.
Still owing Strasburg another $107.6 million over the next four years is quite the hurdle for a club that has already lost at least 56 percent of games played in six consecutive years.
National League Central
5 of 6
Chicago Cubs: Shota Imanaga, LHP
Age/Contract: 32, it's complicated
The Cubs have an option this winter to lock in Imanaga for a total of $57 million for the next three seasons. If they decline it, it becomes a $15 million player option. If he chooses to return, there will be a similar conditional option next winter.
Given their rotation woes, though, the Cubs will probably exercise the option now rather than risk having him walk this winter. And from there, they cross their fingers that he gets the home runs under control.
Cincinnati Reds: Ke'Bryan Hayes, 3B
Age/Contract: 29, $7M in each of 2026 and 2027, $8M in each of 2028 and 2029, $12M club option in 2030
The Reds only have three players signed through 2027. Hunter Greene's contract is the antithesis of a nightmare for them, and owing Jose Trevino $5.25 million with a club option for 2028 is no problem.
So, it's Hayes by process of elimination, even though he has an excellent glove at third base and hit a little better with Cincinnati than he did with Pittsburgh in 2025.
Even at that, though, "a little better" was still an uninspiring .656 OPS. The Reds are going to need to bury him in the lineup for the next four years.
Milwaukee Brewers: Christian Yelich, DH
Age/Contract: 34, $24M in each of 2026, 2027 and 2028, $20M mutual option in 2029
Like Cincinnati, another process-of-elimination pick here in which one of the three possible choices (Jackson Chourio) is a team-friendly dream while another (Aaron Ashby with a $7 million salary in 2027) is too inconsequential to consider a nightmare.
Thus, the pick is Yelich, 33, who was Milwaukee's top slugger in 2025, but who isn't getting any younger. With a salary that makes up roughly one-fifth of the Brewers' payroll budget, they can ill afford to have him start showing his age.
Pittsburgh Pirates: Bryan Reynolds, OF
Age/Contract: 31, $14.25M in 2026, $15.25M annually from 2027-30, $20M club option in 2031
We all know the real contract nightmare in Pittsburgh is figuring out when and what to do about Paul Skenes' long-term future. But 2027 will merely be his first year of arbitration eligibility, so they can continue kicking that can down the road if they so choose.
Reynolds, on the other hand, is locked in for at least another $77.25 million over the next half-decade, and he just had the least productive (non-2020) season of his career.
If he doesn't start slugging again, that contract could get mighty painful.
St. Louis Cardinals: Willson Contreras, 1B
Age/Contract: 33, $18M in 2026, $18.5M in 2027, $17.5M club option in 2028
Take out the first 19 games of the season and Contreras had an .853 OPS over his subsequent 117 appearances, which would have been his best OPS in a season since 2019.
The 33-year-old was also one of the most valuable defensive first basemen in his first year playing there on an even remotely regular basis.
While an expensive, aging veteran is a nightmare for a Cardinals team trying to turn the page to its next chapter, it wouldn't be a surprise if a contender trades for Contreras this winter, after Pete Alonso and Josh Naylor sign in free agency and someone gets a little desperate at first base.
National League West
6 of 6
Arizona Diamondbacks: Eduardo Rodriguez, LHP
Age/Contract: 32, $21M in 2026, $19M in 2027, $17M in 2028
With an honorable mention to Corbin Burnes' six-year, $210 million contract that could be a colossal burden if he's not the same pitcher after returning from Tommy John surgery, Rodriguez has already given the D-Backs back-to-back seasons with both an ERA north of 5.00 and a WHIP of at least 1.50.
It's largely because Rodriguez amounted to nothing for them two years ago that they felt the need to shell out all that money for Burnes last winter.
Colorado Rockies: Kris Bryant, DH
Age/Contract: 34, $27M annually from 2026-28
Signing Bryant was supposed to be Colorado's first step toward mattering again.
Instead, since the acquisition, the Rockies have suffered a dozen more losses than the next-worst team (White Sox) while the 33-year-old has barely played in 25 percent of team games with a sub-.700 OPS.
Because it was only $182 million and not $245 million, this one has consistently landed behind both the Stephen Strasburg and Anthony Rendon contracts on the pain index. But there are three years left in what has already been an all-timer of a disaster.
Los Angeles Dodgers: Tanner Scott, LHP
Age/Contract: 31, $12.6M in 2026, $16.4M in 2027, $16.2M in 2028
During the regular season, Scott was responsible for 23 of L.A.'s 46 saves, while no one else on the roster had more than five. But he blew 10 saves along the way, had a 4.74 ERA and they have opted not to use him yet in the postseason, for fear of the possible consequences.
Not exactly what the Dodgers had in mind one year into his $72 million deal.
San Diego Padres: Xander Bogaerts, SS
Age/Contract: 33, $25.4M annually from 2026-33
The year 2027 is also when Manny Machado's salary spikes to $39.1 million for what will be his age-34 through age-40 seasons. That one could get all sorts of painful, but at least he's still playing well for now.
Bogaerts has already regressed drastically, giving the Padres a .705 OPS over the past two seasons compared to an .880 mark over his final five years in Boston. They still owe him more than $200 million over the course of the next eight years.
San Francisco Giants: Willy Adames, SS
Age/Contract: 30, $13.1M in 2026, $33.1M annually from 2027-31
Credit where it's due, Adames woke up in a big way in the second half. After ending June with nine home runs and a .636 OPS, he was at 21 and .854, respectively, the rest of the way, becoming the first Giant to reach 30 home runs in a season since Barry Bonds in 2004.
As far as Baseball-Reference is concerned, Adames ended up being more valuable this year than in his walk year with Milwaukee. Will he be worth $33.1 million annually in his age-31 through age-35 seasons, though?
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