Projecting MLB's 9 Biggest Nightmare Contracts by 2028
As we wait to find out where Kyle Tucker and Bo Bichette are going to sign what could be decade-long, nine-figure contracts, which currently inked megadeals are most likely to feel like nightmares three seasons from now?
Before we dive in here, let's be sure to specify that we are looking at cash owed, per Spotrac contract data. Not payroll salary or luxury-tax hit, but straight cash, homey, including deferred payments. And, if you can believe it, there are already 24 players scheduled to be paid at least $100M from 2028 onward.
Some of them will be worth every penny.
Others will get all sorts of painful until they mercifully come to an end.
Which ones are which? And which one is likely to be the worst?
Honorable Mentions (1 of 2): Young Enough Not to Worry Yet
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Any number of these could become painful in due time, but each of these players is young enough that he ought to still have several years' worth of "in his prime" seasons left in the tank heading into 2028.
Roman Anthony (21): Owed at least $119M from 2028-33, plus possible escalators and a $30M 2034 club option.
Garrett Crochet (26) Owed at least $114M from 2028-31, plus possible escalators. Can opt out of $30M in 2031.
Vladimir Guerrero Jr. (26): Owed at least $419M from 2028-39, plus possible incentives for All-Stars and MVPs.
Jackson Merrill (22): Owed at least $118M from 2028-2034, but could be as much as $181M, pending MVP votes and plate appearances.
Julio Rodríguez (25): Owed $18M in each of 2028 and 2029 with a club option of at least $240M from 2030-37.
Juan Soto (27): Owed at least $553.75M from 2028-39, but can opt out of the final 10 years, $460M prior to 2030.
Fernando Tatis Jr. (27): Owed $241M from 2028-34.
Bobby Witt Jr. (25): Owed $240M from 2028-2034, plus a three-year, $89M club option for 2035-37. Can opt out prior to any of 2031, 2032, 2033 or 2034.
Yoshinobu Yamamoto (27): Owed $228M from 2028-35, but can opt out after 2029 or after 2031.
Both Yamamoto and Crochet were All-Stars who finished top three in the Cy Young vote. Hard to worry much about either of those pitchers' contracts, unless you're still concerned about Crochet's pre-2024 injury history.
Of the seven hitters here, the only contract that figures to feel even a little bit headache-y heading into 2028 is Rodríguez's. And even that is only because of that convoluted option for 2030 and beyond which needs to be decided upon within five days of the 2028 campaign ending. If he happens to win two of the next three AL MVPs, it becomes a 10-year, $350M club option—which Seattle would presumably be happy to exercise.
Soto's player option after the 2029 season also looms large, although New York will have the option to void the opt out by increasing his salary from $46M to $50M over the course of that decade.
Honorable Mentions (2 of 2): Deferred Pain
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Each of these players is signed to play through at least 2030, but signed to pay through at least 2036, with a total amount still due heading into 2028 of at least $136M.
Mookie Betts (33): Owed $115M to play from 2028-32, plus $120M of deferred payments from 2033-44.
Corbin Burnes (31): Owed $72M to pitch from 2028-30, plus $64M of deferred payments from 2031-36. (Burnes could opt out after 2026, but that is highly unlikely, considering he may miss the entire season while recovering from TJ.)
Dylan Cease (30): Owed at least (possible incentives) $90M to pitch from 2028-32, plus $64M of deferred payments from 2033-2046.
Rafael Devers (29): Owed $135M to play from 2028-33, plus $64.27M in deferred payments from 2035-43.
Francisco Lindor (32): Owed at least (possible incentives) $108M to play from 2028-31, plus $50M in deferred payments from 2032-41.
Shohei Ohtani (31): Owed $12M to play/pitch from 2028-33, plus $680M in deferred payments from 2034-43.
Frankly, all six of these are likely to feel at least a little painful heading into 2028, but at least there's a chance they'll provide some serious value for the 3-6 years they're still contracted to perform.
More than anything, this figures to be when the worm starts to turn on the Dodgers' dynasty.
Betts will be 35 and still owed $235M, while Ohtani will be 33 and still owed $692M. Throw in Blake Snell at 35 and owed nearly $100M and Will Smith at 33 with $77.45M still coming his way and that's more than $1.1B committed to a quartet of current stars who will either be well past or nearing the end of their respective primes.
Burnes' contract might be most painful of all, though, depending on how well he recovers from his injury.
At least the Dodgers have already gotten multiple World Series out of their grand plan, and have the revenue stream to figure out how to stomach all those future payments. The Diamondbacks threw $210M at Burnes, and the next 11 years of paying that off might be brutal if he doesn't bounce back to the dominant force that he was from 2020-24.
9. Austin Riley, Atlanta Braves
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2028 Will Be: Age-31 Season
Remaining on Contract: $22M annually from 2028-32 with a $20M club option for 2033
Compared to some of the gargantuan contracts out there, Austin Riley making $22M per year is almost a drop in the bucket. At any rate, by the time the likes of Kyle Tucker, Bo Bichette and Alex Bregman sign their new contracts this winter, Riley isn't even going to rank top 40 in 2026 salary.
All the same, his past two seasons have made that 10-year deal look less and less like an actual deal.
2021-23 Riley: .286/.354/.525, 36.0 home runs and 159.3 games played per season, 18.8 bWAR
2024-25 Riley: .258/.316/.445, 17.5 home runs and 106.0 games played per season, 4.2 bWAR
Riley missed two weeks in May 2024 with an oblique injury and the final six weeks of that season with a fractured hand. And after making it almost to the All-Star Break unscathed this past season, more core injuries caused him to miss 60 of Atlanta's final 69 games.
Worse yet, while appearing in each of Atlanta's first 93 games in 2025, his numbers were way down. He hit 27 home runs in his first 93 games of 2022, but he was operating at a 162-game pace of 24.4 last year.
Can he bounce back, or did he peak in his mid-20s?
If it's the latter, how much worse might things get by his mid-30s?
8. Aaron Judge, New York Yankees
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2028 Will Be: Age-36 Season
Remaining on Contract: $40M annually from 2028-31
Fresh off his third AL MVP in the span of four seasons, it feels a little idiotic to question Aaron Judge's ability to keep performing at a high level for the duration of this nine-year contract.
When he signed that $360M deal, though, there were plenty of external concerns about his injury history and whether the latter few years of this contract would be as painful for the Yankees as the Albert Pujols and Miguel Cabrera ones were for the Angels and Tigers, respectively.
So far, so good, of course. Judge did miss about a third of the 2023 campaign, most of that due to a toe injury. Even so, he has the second-highest batting average (behind only Luis Arraez) and the second-most home runs (behind only Shohei Ohtani) in all of baseball over the past three seasons.
These were the years the Yankees fully expected him to be great, though, and it doesn't change the fact that there has not been a single player in the past four years who hit at least 25 home runs in his age-36 season or older.
By no means does that mean Judge can't do it. He may well age just as gracefully as David Ortiz and Nelson Cruz did, each hitting at least 160 home runs from his age-36 season onward.
If that's not the case, though, the final $160M on this contract will sting.
7. Willy Adames, San Francisco Giants
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2028 Will Be: Age-32 Season
Remaining on Contract: $28M annually from 2028-31
Season No. 1 of Willy Adames' seven-year, $182M contract ended up being pretty solid.
It certainly didn't start out that way, as he hit .193/.281/.303 while starting each of San Francisco's first 65 games. But one random Sunday off in early June followed by a shift in the batting order was just what the doctor ordered, hitting 25 home runs and posting an .848 OPS the rest of the way.
Adames ended up getting to 30 home runs, which hadn't been done by a San Francisco Giant since Barry Bonds clubbed 45 back in 2004.
He always has been a late bloomer, hitting far better in July and August than he has in March and April throughout his career.
But can this zero-time All-Star keep being a second-half hero into his mid-30s?
And at what point does that second-half prowess turn into postseason production? Adames hasn't homered in any of his last 30 playoff games, posting a .196/.310/.258 triple slash dating back to his final appearance in the 2019 ALDS.
He did at least bounce back a bit from what was an atrocious final season of glovework in Milwaukee, but he has never won a Gold Glove and certainly wasn't close to getting one in 2025. If Adames regresses in that regard moving forward, this contract could get really painful—especially if the Giants wind up with Bryce Eldridge as the regular first baseman and Rafael Devers as the primary designated hitter, leaving nowhere to hide Adames' glove.
6. Mike Trout, Los Angeles Angels
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2028 Will Be: Age-36 Season
Remaining on Contract: $35.45M annually from 2028-30
Mike Trout was healthier than usual in 2025, appearing in 130 games. He did miss most of May with a knee injury, but otherwise played in all but six games, kept fresh by not making a single appearance in the field after April 30.
There is an unfortunate side of Trout making enough plate appearances to qualify for a batting title for the first time since 2020, though.
It was a big enough sample size to suggest that Trout is already past his prime.
See, for a while, Trout was rarely healthy, but still pretty great for the portions of the season that he wasn't on the IL. From 2021-24, he missed nearly 60 percent of Angels games, but posted a .951 OPS and averaged 46.3 home runs per 162 games played when available.
In 2025, his OPS was .797—a solid mark for most mortals, but laughable by Trout's former standards—his HR% (4.7) was the lowest it has been since 2016 and his K% (32.0) was the worst of his career.
He still mashed the occasional moonshot, including going 485 feet on the 400th home run of his career. However, he's nowhere near the consistent force he used to be.
And that was 2025. We're talking about 2028 here—a season in which Trout will turn 37 in August, with two more expensive years still to come.
At least by 2028, though, it's only going to be a little more than $100M left on his contract. And at least it's no longer going to be a case of paying both Trout and Anthony Rendon a combined sum of more than $70M per year to rehab from various injuries. That keeps him from landing in the top five.
5. Corey Seager, Texas Rangers
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2028 Will Be: Age-34 Season
Remaining on Contract: $31M annually from 2028-31
While Corey Seager's injury history isn't quite as extensive as Mike Trout's, he has missed at least 39 games in each of the past three seasons, getting a reputation for inevitable time spent on the shelf.
And how often do injury-prone shortstops suddenly figure out how to stay healthy in their mid-30s?
Better yet, how often do shortstops provide any real value into their mid-30s regardless of their injury history?
Derek Jeter fared pretty well into his late-30s, even batting .316 in his age-38 campaign. But that was a rarity and it was 13 years ago. The only example worth mentioning in the past decade was Brandon Crawford flirting with an NL MVP in his age-34 season—and even he had a .618 OPS from that point forward.
Granted, Seager doesn't have to remain a shortstop. By the time 19-year-old top prospect Sebastian Walcott is ready for the Rangers' gig, Joc Pederson will be out of the picture and Seager could become the full-time DH. That could buy him a few more years of good production, as he did still have an .860 OPS this past season for the 102 games he didn't miss.
At this point, though, we'll believe he can stay healthy when he actually does it again, and that skepticism for 2028-31 will only exponentiate if he misses significant chunks of the next two seasons.
4. Max Fried, New York Yankees
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2028 Will Be: Age-34 Season
Remaining on Contract: $29M annually from 2028-32
For the most part, Max Fried had a dynamite first season with the Yankees.
There was a rough patch of about six weeks during the doldrums of the summer, and he did get lit up by the Blue Jays in Game 2 of the ALDS. However, he made 20 quality starts and had a sub-3.00 ERA, which only six other pitchers can boast. Also, the average velocity on his four-seamer was almost two MPH greater than it had been in any of his previous seasons with Atlanta. Hard to argue with that.
But when the Yankees signed Fried to an eight-year deal less than 48 hours after Juan Soto signed with the Mets, it wasn't the 2025 portion of the contract that made it feel like a panic-driven pivot by the Bronx Bombers.
It was the sheer length of the contract given to a pitcher who A) was already just one month away from turning 31 and B) dealt with forearm strains in both 2023 and 2024.
Already, neither his curveball nor his changeup is as devastating as it used to be. His worst xSLG against either pitch in any season from 2020-23 was a .272 mark against the curve in 2020. However, it has been at least .321 against each pitch in each of the past two seasons. (Which, to be clear, is still quite good, but simply not as good.)
Something to keep an eye on over these next few years. Because with the contracts on both Gerrit Cole and Carlos Rodón expiring after 2028, the Yankees might be desperate for the latter half of Fried's deal to produce some serious fruit.
3. Trea Turner, Philadelphia Phillies
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2028 Will Be: Age-35 Season
Remaining on Contract: $27.27M annually from 2028-33
As previously mentioned in Corey Seager's section, shortstops aren't exactly renowned for their tendency to age like a fine wine.
For every Ozzie Smith or Omar Vizquel who managed to have an All-Star season at age 35 or older, there are a few dozen shortstops who abruptly went from "really good" to "replacement level" in their early 30s.
And Trea Turner will turn 40 before this contract expires.
For right now, it's a good contract. Turner won his second career batting title in 2025, placing fifth in the NL MVP vote despite missing three weeks in September. He has racked up a combined total of 62 home runs and 85 stolen bases over the first three seasons of this 11-year deal.
But the Phillies also just re-signed Kyle Schwarber through 2030, so opportunities to DH are going to be few and far between for Turner over the next half-decade. Transitioning to the less demanding first base isn't exactly an option, either, as Bryce Harper is signed through 2031.
It's shortstop or bust for the foreseeable future, and it'll be interesting to see how that plays out if and when Turner starts to lose a step.
2. Manny Machado, San Diego Padres
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2028 Will Be: Age-35 Season
Remaining on Contract: $40M annually from 2028-33
Thus far, Manny Machado has shown no serious signs of slowing down at the dish. He won a Silver Slugger in each of the past two seasons, going for a combined total of 56 home runs, 63 doubles, 200 RBI and 25 stolen bases.
He has now posted an OPS of at least .739 in each of his 14 seasons, and he might get to 400 career home runs by the end of 2026.
Already, though, he has declined from an asset to a liability at the hot corner.
In 2023, Machado had a Statcast Fielding Run Value of +10 and an Outs Above Average grade of +12, but he was at minus-4 and minus-6, respectively, in 2025. He "led" all NL third basemen with 16 errors.
And if he was that mediocre in 2025, how much worse will his defense be in 2028? Or 2033?
Hiding that glove by transitioning Machado to a full-time DH role could be an option as early as this coming season. Not only do the Padres not have a full-time DH in place, but they signed Sung Mun Song from KBO and he can play third base.
Even if they do that, though, $40M per year is going to get painful long before Machado turns 41 midway through the final season of this deal. He is a great hitter, but he's no Aaron Judge. And he's only going to get less Judge-like the older he gets.
1. Xander Bogaerts, San Diego Padres
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2028 Will Be: Age-35 Season
Remaining on Contract: $25M annually from 2028-33
In the five seasons before signing his 11-year, $280M contract during the 2022-23 offseason, Xander Bogaerts triple-slashed .300/.373/.507, averaging 26.5 home runs and 101 RBI per 162 games played. He was also worth 5.9 bWAR per 162 games played and received AL MVP votes in each of those five seasons.
Between years No. 2 and 3 of that mega deal, though, Bogaerts has already been a shell of what he once was. His triple-slash in 2024-25 was .263/.319/.386, averaging 14.4 home runs, 63.6 RBI and 2.1 bWAR per 162 games played.
Basically, he went from 2024-25 Vladimir Guerrero Jr. levels of production to 2024-25 Sal Frelick levels of production. (Bogaerts has at least played better defense for the Padres than he did for the Red Sox, though.)
And there are still eight years left on his contract.
Contrary to Trea Turner and Corey Seager—who are still quite good, but land in the top five because they need to overcome a long history of middle infielders struggling to remain even "replacement level" effective after they turn 35—Bogaerts has already declined sharply since turning 31 and is well on his way to becoming the next Kris Bryant or Anthony Rendon type of staple in these periodic conversations about the worst contracts in the sport.
