Predicting MLB's 10 Biggest Nightmare Contracts by 2026

It only takes one, maybe two bad contracts to derail a Major League Baseball franchise for at least half a decade.

Take my beloved, downtrodden Washington Nationals, for example. Not only have they been stuck paying outrageous sums of money to both Stephen Strasburg and Patrick Corbin (and still making deferred payments to Max Scherzer) for the past several years, but those contracts kept them from being able to keep stars like Bryce Harper, Trea Turner and Juan Soto, causing them to plummet from 2019 World Series champions to the fewest wins in all of baseball over the past three years combined.

So, two years from now, which contracts are most likely to become a franchise-crippling albatross?

The only real criterion here is that the player presently must be owed at least $50 million* for 2026 and beyond. Anything less than that isn't really a nightmare so much as it is a considerable nuisance, as was the case this past season for the final year of Miguel Cabrera's contract—which absolutely was a nightmare until its final chapter.

Presently is a key word in that qualification, as we will not be including unsigned free agents. Depending on the duration and size of the contracts, Blake Snell, Cody Bellinger, Jordan Montgomery and others could become solid candidates for this list in the coming days. But we can only use contracts already on the books.

Beyond that, it's really just a question of which players seem most likely to invoke a "We still owe that guy how much and for how many more years?!" response among the team's fans heading into the 2026 campaign.

These 10 players are ranked in ascending order of how visceral those responses might be.

*Examples of contracts that might be terrible but don't meet that $50 million threshold: Javier Baez ($48 million from 2026-27), Byron Buxton ($45 million from 2026-28), Yu Darvish ($43 million from 2026-28), Joe Musgrove ($40 million from 2026-27), Anthony Rendon ($38 million in 2026), Sonny Gray ($35 million in 2026), Andrew Benintendi ($31 million from 2026-27), Robbie Ray ($25 million in 2026). Even without those big numbers included, there are still 42** players who will still be owed at least $50 million at the start of 2026.

**Does not include Wander Franco's contract, which we are excluding from this conversation, given the uncertainty on whether he'll be allowed to play again or whether Tampa Bay will have to pay him.

Tyler Glasnow, RHP, Los Angeles Dodgers ($81.6 million from 2026-28)

Given how well Glasnow has pitched when healthy, he is easily worthy of the $27.3 million average annual value (AAV) on his new five-year contract. But given that 2023 was the first time he made more than 14 starts—and still only managed 120 innings pitched—there is justifiable concern that he'll enter 2026 as much more of a question mark than a sure thing of a quality starter, as was the case with the likes of Chris Sale and Jacob deGrom this past season.

Jung Hoo Lee, OF, San Francisco Giants ($85 million from 2026-29, with a player opt-out available after 2027)

A career .340 hitter in seven seasons in the KBO, the 25-year-old Lee might end up being a colossal bargain on his six-year deal with an AAV of $18.8 million. But if he struggles to adjust to MLB pitching, then the mildly back-loaded structure of this contract — $12M, $16M, $22M, $22M, $20.5M and $20.5M—becomes a problem for a Giants franchise which typically avoids these long-term pacts for that very reason.

Jake Cronenworth, 1B/2B, San Diego Padres ($60 million from 2026-30)

This one certainly doesn't look great after Cronenworth's OPS dropped for a third consecutive season to just .689 in 2023. But even if he is completely unplayable by 2026, $12 million per year for five years hardly seems like a nightmare situation. Heck, $12 million is less than the deferred payments the Nationals will still be making to each of Max Scherzer and Stephen Strasburg in 2026.

Yoshinobu Yamamoto, RHP, Los Angeles Dodgers (Owed an estimated $271 million from 2026-2035, but with player opt-outs available after 2029 and 2031)

Simply put, a guaranteed 12-year deal for a pitcher is a bit terrifying. Especially for one who has yet to throw a pitch in the majors. But I refuse to classify this one as a potential nightmare until we get a full year of the Yamamoto experience to find out if it's plausible he might even exceed the value of his contract.

Fernando Tatis Jr., OF, San Diego Padres ($286 million from 2026-34)

This one sure looked like a nightmare a year ago while Tatis was serving his 80-game performance-enhancing-drug suspension and recovering from yet another injury. But the shortstop-turned-outfielder had a fantastic 2023 campaign, just turned 25 on Jan. 2 and reasonably should be quite valuable for the next decade. That 14-year, $340 million contract was quite back-loaded, though, and he'll be owed an average of $31.8 million over the final nine years of the deal.

Giancarlo Stanton, OF/DH, New York Yankees ($64 million from 2026-28)

The saving grace keeping Stanton out of the top 10 is the fact that this $64 million is split almost evenly between the Yankees and Marlins, as Miami retained $10 million for each of 2026, 2027 and 2028, meaning he's only actually owed $34 million by New York for 2026 and 2027 (and another $15 million for 2028, should they pick up his club option).

Contract: $26 million annually from 2026-28 ($78 million total owed)

2023 Stats: .233/.313/.367, 10 HR, 31 RBI, -1.0 bWAR

To put it lightly, the first two years of Kris Bryant's seven-year, $182 million deal with the Rockies didn't go well.

Already, he has missed 202 games, after missing a combined total of just 148 games in his first seven seasons in the majors. Injury history wasn't really a concern when he signed the contract, but now it has become a major issue.

At least in 2022, he was reasonably productive while healthy, posting an .851 OPS. But this past season, he missed half of Colorado's games and played quite poorly in the other half with a .680 OPS. Save for struggling in the truncated 2020 campaign, it was the first time he had posted an OPS below .830.

That's with the Rockies, too, where you benefit from the thin air in half your games. If anything, you should really post your highest-ever OPS after signing with Colorado, not your worst by a margin of 150 points.

So, where do Bryant and his full no-trade clause go from here?

Right now, it's one of the biggest nightmare contracts in the majors.

Two years from now, at least the total remaining cost will be down to $78 million, which keeps it below a handful of nine-figure deals in our top nine. But it does feel like the Rockies are going to be stuck in the NL West basement for the duration of this contract they hoped might put them back on the map.

Contract: $40 million annually from 2026-31 ($240 million total owed)

2023 Stats: .267/.406/.613, 37 HR, 75 RBI, 4.5 bWAR

The reason the Yankees balked at signing Aaron Judge to a massive long-term extension prior to the 2022 campaign when he had one year left on his rookie deal was his injury history. He missed 50 games in 2018, 60 games in 2019 and more than half of 2020 before finally enjoying back-to-back mostly healthy years in 2021-22.

After he clubbed an AL-record 62 home runs in the latter year, the Yankees had to go to a nine-year, $360 million price point to keep their star slugger.

But already, those injury woes have bitten the Yankees, as he missed 56 games in the first year of that massive contract while they sputtered to an 82-80 disappointment.

And how many guys who were injury-prone throughout their 20s suddenly enjoy a healthy run through their 30s?

Oh, Judge was still fantastic while healthy in his age-31 season. He always has been. His .993 OPS since the beginning of 2017 is the second-highest in the majors, trailing only Mike Trout's mark of 1.032. And with his strength and physical stature, it's plausible he'll still be mashing home runs at a 162-game pace of 40-plus well into his late 30s.

Over the final six years of this contract, though, what percentage of New York's games do you think Judge will start?

Anything below 75 percent would probably turn this contract into a nightmare.

Contract: $27.27 million annually from 2026-33 ($218.18 million total owed)

2023 Stats: .266/.320/.459, 26 HR, 76 RBI, 102 R, 30 SB, 3.4 bWAR

Four months into this massive contract, it looked like the Phillies bought themselves a lemon of a shortstop. Trea Turner was hitting just .236 with a .656 OPS—and let's just say he wasn't using his glove to make up for those struggles at the dish—through his first 108 games.

But he was outstanding from August 5 onward, hitting .339 with a 1.069 OPS and boasting 162-game paces of 221 hits, 55 home runs and 141 RBI over his final 47 games of the regular season. He proceeded to hit .347 with three home runs in Philadelphia's 13-game postseason run.

Better late than never, and that 11-week surge inspired a fair amount of hope that Turner will be able to live up to his 11-year deal.

We shall see how the next two seasons go, though, which will dictate how everyone feels about this contract heading into 2026.

Turner will be 32 at the beginning of that season with eight years left on his deal. Not many shortstops have played beyond their age-35 season, and fewer still are actually productive into their late 30s. But maybe Turner will be one of the exceptions to the rule, like Derek Jeter or Ozzie Smith, both of whom were All-Stars at the age of 40.

If he starts to fall apart by 32, though, woof. At least the Phillies will be done paying both Kyle Schwarber and JT Realmuto after 2025, but that would be a tough pill to swallow for a long time.

Contract: $2 million annually from 2026-33, $68 million annually from 2034-43 ($696 million total owed)

2023 Stats: .304/.412/.654, 44 HR, 95 RBI, 20 SB; 132.0 IP, 3.14 ERA, 1.06 WHIP, 11.4 K/9, 10.0 bWAR

By deferring so much of Shohei Ohtani's $700 million contract, the Los Angeles Dodgers were able to get the present value of his deal down to a still-record-setting $460.8 million.

But, eventually, that bill will come due, and there will be a tipping point where what currently feels like a massive exploitation of a loophole will pivot into a conundrum for the franchise to deal with.

That tipping point probably won't be until at least the 2028-29 offseason, when Ohtani will be 34, possibly starting to decline and still owed what at that point would be $690 million over the next 15 years.

It could come sooner, though, if he doesn't regain his dominance on the mound.

We already know Ohtani won't be pitching in 2024. However, if he struggles and/or reinjures his elbow in 2025, we'll go into 2026 almost needing to assume he won't be a starting pitcher again, and viewing any pitching contributions over the remainder of the contract as a bonus rather than an expectation.

And if that becomes the case, he might need to hit .300/.400/.600 with 100 home runs and 200 RBI between the next two seasons—numbers he can certainly reach—to still feel worth his contract by 2026.

Whether the Dodgers win the 2024 and/or 2025 World Series will also play a big role here.

If Ohtani is the back-to-back World Series MVP and maybe NL MVP in one of those years, no one is going to much care how much he is owed from that point forward; he'll already be worth the contract. But if they get bounced in the NLDS in each of the next two Octobers or even miss a postseason altogether, Ohtani's contract might take the brunt of the outrage.

Contract: $38 million in 2026, $37 million in 2027 ($75 million total)

2023 Stats: 30.1 IP, 2.67 ERA, 0.76 WHIP, 13.4 K/9, 0.9 bWAR

Jacob deGrom has been an all-time great when healthy. In 1,356.1 career innings pitched, he has a 2.53 ERA and 0.99 WHIP. Among the 610 pitchers to log at least 1,000 innings dating back to 1969, he has the best WHIP and the third-best ERA.

However, he couldn't stay healthy in 2021 or 2022 and was already 34 years old when the Rangers shockingly signed him to a five-year, $185 million deal last winter.

And to the surprise of no one, he lasted just six starts with Texas before undergoing Tommy John surgery, which may well keep him out for all of 2024.

Maybe it's exactly the operation (and dedicated rest and recovery time) deGrom needed in order to end his career on something of a high note after missing so much time in recent years with various forearm, elbow and shoulder injuries.

But would even an eternal optimist be willing to make that bet on an older pitcher recovering from his second TJ surgery after four straight truncated seasons?

At least by 2026, this contract isn't that much of a disaster anymore, as it's the only one in our top 10 that doesn't run through at least 2028. If deGrom never makes it back to full strength, though, the $75 million for those final two seasons will be painful—for a team that is also slated to spend a combined $115 million on Corey Seager and Marcus Semien between those two years.

Contract: $35.45 million annually from 2026-30 ($177.25 million total owed)

2023 Stats: .263/.367/.490, 18 HR, 44 RBI, 2.9 bWAR

Because of how banged up Mike Trout has been over the past three seasons, his contract is already a top-10 nightmare heading into 2024.

The Angels still owe $248.15 million to a guy who has missed more than 50 percent of team games since the beginning of 2021, who just posted his worst batting average, OBP and slugging marks in more than a decade and who has yet to partake in a postseason victory in his career.

But while some of the current biggest nightmares (Stephen Strasburg, Anthony Rendon, Javier Báez) will "graduate" out of being colossal eyesores by 2026, Trout will still be owed an awful lot of that 12-year, $426.5 million contract signed in March 2019.

At that point, Trout will be 34 years old and a 15-year MLB veteran with five years remaining on his contract.

Even if he's mostly healthy and productive in both 2024 and 2025, 2026 was always likely to be where we started to see diminishing returns from what will be a first-ballot Hall of Famer one day.

If the Angels happen to be viewed as a contender heading into 2026—or if Trout gets traded to a contender within the next two years—his contract won't seem so bad. But with Shohei Ohtani gone while Trout and Rendon continue to eat up more than $75 million per year, that might be a pipe dream.

Contract: $25 million annually from 2026-33 ($200 million total owed)

2023 Stats: .285/.350/.440/.790, 19 HR, 58 RBI, 19 SB, 4.4 bWAR

Of the four shortstops who signed nine-figure contracts last offseason, Xander Bogaerts' was the most concerning one, even as the ink was still drying on those deals.

The $25.45 million AAV wasn't the problem. After five consecutive years earning AL MVP votes—during which time he hit .301/.373/.508 and was a three-time All-Star and three-time Silver Slugger—Bogaerts certainly deserved to be made one of the 25 highest-salaried players in the game.

However, giving an 11-year contract to a 30-year-old shortstop was inevitably going to look like a questionable move at some point.

And after a debut year in San Diego in which Bogaerts already posted a worse average, on-base percentage and slugging percentage than he had in any of his final five seasons in Boston, we might already be at that point—and almost certainly will be there by 2026.

To be clear, we're not saying Bogaerts played poorly in 2023. But he indisputably was not as valuable as he had been for the past half-decade, and the natural assumption is that his production will really begin to decline by his age-35 season, if not sooner.

San Diego had to know it was taking a big risk with the back half of this contract, but it did assume Bogaerts would be a big part of a postseason-bound team in 2023 and a World Series winner within his first five years on the roster. That first season definitely didn't go according to plan for the Padres, and they already seem to be hitting the eject button on that World Series window.

Contract: $27 million annually from 2026-28 ($81 million total)

2023 Stats: 64.1 IP, 6.85 ERA, 1.45 WHIP, 9.0 K/9, -0.9 bWAR

Everyone already knew last offseason that Carlos Rodón was an injury risk. He pitched a full, 178-inning season in 2022, but only after averaging 73.0 innings pitched over the previous five years.

Nevertheless, the Yankees took a chance on the southpaw who was a Cy Young candidate in both 2021 and 2022, signing Rodón to a six-year, $162 million deal.

And year No. 1 was an absolute disaster.

Rodón started the year on the IL with a forearm strain suffered during spring training, remained on the IL until July with a back injury and landed back on the IL with a hamstring injury just one month after his Yankees debut.

All told, he made just 14 starts, and struggled in most of them.

Even before ending the year by allowing eight earned runs without recording a single out against the lowly Royals, Rodón already had a 5.74 ERA and was a major disappointment. That final start was merely the cherry on the awful sundae.

Could he bounce back? Sure. Rodón had an 8.22 ERA in his very limited action in 2020 before posting a 2.37 ERA in 2021.

But he has now had two great seasons and three atrocious, injury-riddled seasons in the past five years, and the great seasons might have been fools' gold.

Contract: $31.5 million in 2026, $30.5 million in 2027, $30 million in 2028 ($92 million total, plus vesting options for 2029-32 which could drive the total cost up to $162 million)

2023 Stats: .230/.312/.399, 18 HR, 65 RBI, 1.4 bWAR

First and foremost with Carlos Correa, there are the medical history concerns which caused both the Giants and the Mets to rescind his $300-plus million offers last winter. Those teams were seemingly worried that because of his surgically repaired lower right leg, once Correa's late-career decline begins, it could be a swift drop off a cliff.

But that's why this already felt like a possible eventual nightmare from the moment the contract was signed.

Now that he's one disappointing year into the deal, though, Correa's contract is even more of a long-term concern for a small-market franchise that can't exactly afford to be throwing away more than $30 million per year.

Even if the medical history concerns didn't exist, Correa posted the lowest WAR of his career in 2023, struggling to get into any sort of groove and missing time late in the year while dealing with plantar fasciitis in his left foot. (He did show up in a big way in the postseason, though, with a .409 batting average in those six games.)

Correa is still only 29 years old, though. Maybe it was just a down year after a tumultuous offseason and he'll bounce back in a big way for the next half-decade.

Conversely, if he doesn't perform at anything close to an All-Star level over the course of the next two seasons, Minnesota could be forced to deal with a disaster that both San Francisco and New York managed to avoid.

Contract: $21 million in 2026, $40 million annually from 2027-33 ($301 million total owed)

2023 Stats: .258/.319/.462, 30 HR, 91 RBI, 2.9 bWAR

When the San Diego Padres signed Manny Machado to a 10-year, $300 million contract during the 2018-19 offseason, it included a player opt-out after the 2023 campaign. And rather than risk losing him this offseason, they re-signed him to an 11-year, $350 million contract back in February.

Already, they might be regretting that decision.

And by two years from now, it might be a full-blown disaster for them.

They surely didn't know in February that they would be looking to slash payroll this offseason, otherwise they would have just kept the status quo and risked letting Machado walk.

Instead, they re-upped with a third baseman who—by his five-time top-10 MVP vote-getter standards—really struggled in his age-30 season, posting a sub-.800 OPS for the first time since 2017.

At the start of 2026, Machado will be 33 and still owed more than $300 million, which already should have terrified the Padres even as they were signing him 10 months ago, fresh off his second-place finish in the NL MVP vote.

Now that he's coming off a down year, it's an even more frightening proposition for a franchise that already has a staggering $145.5 million payroll for 2027.

Maybe Machado will still be worth his big salary in the 2026-29 timeframe, but looking ahead to the final few years of that contract could make it the biggest nightmare situation in the majors two years from now.