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Stephen Strasburg retired, Patrick Corbin’s deal with the Washington Nationals finally expired and Chris Sale roared back to form in a major way.
That means there are changes to the annual rankings of MLB’s worst contracts. With Black Friday deals in the past and baseball’s hot stove on the verge of heating up, risk-averse executives often point to the league’s underwater contracts as justification for trusting internal development or otherwise standing pat with mediocre rosters.
Such reasoning can amount to an excuse, of course. But there’s no denying free agency can be a gamble. Even lesser deals without massive publicity don’t work out. Think Jeimer Candelario in Cincinnati or Mitch Haniger in San Francisco and now Seattle. In the case of Pittsburgh’s Ke’Bryan Hayes, even the en vogue pre-arbitration extension isn’t looking like a wise investment for a notoriously penny-pinching ownership.
Elsewhere, big-money deals to shortstops like Carlos Correa and Dansby Swanson are fine for now, but hints of injuries or regression leave room for serious concern about the future.
Some deals, however, are already outright flops with higher salaries and much higher stakes.
Those stand alone as the worst contracts in the league.
Original deal: Five years, $100 million
Remaining years:
2025: $20 million
2026: $20 million
Castellanos was fresh off the best season of his career when the Phillies signed him in March 2022. In the three years since, Castellanos’ time with the Phillies has provided doses of nearly every emotion. Frustrations have been offset by heroic moments, colorful quotes and charming shots of Castellanos celebrating with his son.
Despite being part of thrilling playoff runs, the Phillies have yet to win it all with Castellanos aboard. And his tenure has ultimately not been worth near his salary. Castellanos has been worth only 1.4 fWAR over the past three seasons. His first year was a struggle. His 29 homers in 2023 seemed like a step in the right direction. But even when the power shows up, Castellanos has remained free-swinging and prone to severe slumps. Despite playing 162 games in 2023, Castellanos was worth 0.4 fWAR. His 105 wRC+ was only a tick above league average. Over the past three years, his minus-28 defensive runs saved is the worst total among all MLB outfielders.
Now there are whispers of the Phillies trying to trade Castellanos as they look to retool their roster. But the question looms: Will they have any takers?
Original deal: Six years, $162 million
Remaining years:
2025: $27.833 million
2026: $27.833 million
2027: $27.833 million
2028: $27.833 million
Rodón’s big-money deal looked like a disaster after he posted a 6.85 ERA in 2023, his first year in the Bronx. Rodón made small steps toward redemption this past season, throwing 175 innings with a 3.96 ERA and averaging 10 K/9. Although Rodón was much improved from that disastrous 2023, he has a long way to go to live up to the high AAV the Yankees will pay him for four more seasons.
Rodón was worth only 1.7 fWAR this past season and lasted only 3 1/3 innings in his lone World Series outing. The good news is that Rodón had a 2.91 ERA in the second half and saw his strikeout numbers return to near-elite levels after the All-Star break. However, the 31 home runs Rodón surrendered in 2024 tied for the second-highest total in the majors.
Original deal: 11 years, $280 million
Remaining years:
2025: $25,454,545
2026: $25,454,545
2027: $25,454,545
2028: $25,454,545
2029: $25,454,545
2030: $25,454,545
2031: $25,454,545
2032: $25,454,545
2033: $25,454,545
When the San Diego Padres signed Bogaerts at Winter Meetings in 2022, it was immediately a polarizing decision. On one hand, it was another aggressive move to bring another All-Star to San Diego. On the other hand, 11 years is an awfully long time. Bogaerts is only two seasons into this contract, and though he’s still an above-average player, there are already signs of decline.
In 2024, Bogaerts’ wRC+ fell to 95, below the league average of 100, for the first time since 2017. He homered only 11 times in 111 games. And worse from a value standpoint, Bogaerts has already moved away from shortstop, playing 85 games at second base this past season. Bogaerts returned to shortstop in September, but he’s never graded well at the position. Going forward, the Padres are also paying Manny Machado more than $39 million annually through 2033, so they must hope Bogaerts can fend off further decline as he enters his age-32 season. San Diego will pay him until he is 40.
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The Rangers’ gamble on Jacob deGrom hasn’t paid off. (Tim Heitman / Imagn Images)
Original deal: Five years, $185 million
Remaining years:
2025: $40 million
2026: $38 million
2027: $37 million
2028: $37 million (mutual option)
The Rangers have already paid Jacob deGrom $70 million for only nine starts. The deal has so far been a predictable money pit for a pitcher who has not surpassed 92 innings since 2021.
When healthy, deGrom has still looked like one of the best pitchers in the sport. He returned from the second UCL reconstruction of his career and allowed only two earned runs in three starts with the Rangers this past season. Over his 41 innings with the Rangers, he has a 2.41 ERA and has averaged 13 K/9.
Getting deGrom back on the mound this season was a positive step, even if it took longer than initially hoped. Although deGrom enters the offseason healthy, he is now 36, and the Rangers are paying him top-shelf money for several more seasons.
Original deal: 12 years, $426 million
Remaining years:
2025: $37,116,666
2026: $37,116,666
2027: $37,116,666
2028: $37,116,666
2029: $37,116,666
2030: $37,116,666
With all the money left on the table, there’s a real argument for Trout to be No. 1 on this list. But because he is Mike Trout and because, when healthy, he’s still had a 134 OPS+ over the past two seasons, we will resist such a harsh assessment for now. Still, 2025 could be a crucial year for Trout to prove he’s still among the game’s stars.
Trout’s career path has come to mirror Ken Griffey Jr.’s in ways good and bad, an all-time talent who keeps succumbing to injuries. Even if Trout keeps hitting, his speed and defense may never again be the tools they once were. While the Angels wrestle with even bigger problems, they’ve also discussed Trout moving away from center field and spending more time at the outfield corners or DH. We’ve got a long way to go before 2030.
Original deal: Six years, $140 million
Remaining years:
2025: $22.5 million
2026: $25 million (opt-out)*
2027: $25 million
(*If Story opts out after 2025, the Red Sox can opt back in by activating an additional $25 million in 2028.)
It was still April when Trevor Story dove for a ball and landed awkwardly. As Story grimaced, Red Sox nation groaned. The left shoulder dislocation cost Story the majority of the year, and now three years into a deal marred by injuries, the Red Sox must hope there’s still something left in Story’s bat.
In only 163 games over the past three years, Story has a mere .296 on-base percentage and an 89 OPS+. He made a surprise return from the shoulder injury and hit .270 with two home runs in September, providing a small glimpse of hope. But after all the injuries, the chances of Story taking his opt-out after this coming season are slim. As the Red Sox look to return to contention, they must hope Story can stay healthy and find his form of old even as he enters his age-32 season.
Original deal: 13 years, $325 million
Remaining years:
2025: $32 million
2026: $29 million*
2027: $25 million*
2028: $25 million (club option)*
(*Marlins will pay $10M.)
If you watched the MLB postseason, you know Giancarlo Stanton can still change a baseball game. We are still witnessing a potential Hall of Famer with majestic power. There’s still a place for him on the Yankees. But the harsh truth is he’s not worth anywhere near his enormous salary these days. For as much as playoff heroics — seven home runs and a 1.048 OPS — might have calmed some of the outcry, Stanton has been worth only 1.3 fWAR over the past three seasons.
Although his power still looms large, he hasn’t had an on-base percentage over .300 since 2021. Mostly a DH, Stanton played 33 games in the outfield last season and was worth minus-3 defensive runs saved. Stanton is 35 and already among the slowest players in the league. FanGraphs estimated Stanton’s production to be worth $6.2 million this past season, but the Yankees will pay him much more for the next three years.
Original deal: Six years, $140 million
Remaining years:
2025: $25 million
2026: $24 million
2027: $24 million
The Story contract still looks good in comparison with Báez. The two shortstops signed for identical amounts in the 2021-22 offseason. Báez has played far more games (360), which has only elevated the reasons for dismay. Over the past two years, Báez’s 56 wRC+ is the fourth worst among players to receive at least 500 plate appearances. Although he’s still capable of magical plays in the field, he was worth minus-4 defensive runs saved and minus-1 outs above average in 2024.
Báez finally underwent hip surgery in August. Tigers president of baseball operations Scott Harris said Báez is expected to “have a fighting chance to be ready for Opening Day,” and it seems he is in Detroit’s plans once again in 2025. He may be a mere platoon player next season, and it is still difficult to envision Báez finishing this contract as the Tigers improve their trajectory. Perhaps the oddest part: The notoriously strikeout-prone Báez has actually cut his K-rate sharply since coming to Detroit, from 33.6 percent in 2021 to 23.9 percent last season. In turn, however, Baez’s power has been zapped and his ability to hit fastballs has greatly diminished.
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Kris Bryant has produced -1.4 fWAR in three seasons with the Rockies. (Isaiah J. Downing / USA Today)
Original deal: Seven years, $182 million
Remaining years:
2025: $27 million
2026: $27 million
2027: $27 million
2028: $27 million
Javier Báez’s contract is an albatross. The Yankees declined their option on Anthony Rizzo. And still no member of the once-great Cubs core is struggling more than Kris Bryant. The player who won an MVP at 24 has played only 159 games over three seasons with the Rockies. His performance at the plate has declined in each of those three seasons. A negative WAR player over the past two years, Bryant has battled plantar fasciitis and multiple back issues. Now dealing with severe arthritis, Bryant has indicated he hasn’t had any thoughts of retirement. At the same time, he’s well aware of how rough the situation has become.
“I’m not going to sugarcoat it, it’s been terrible,” he told reporters in September. “It’s been terrible on me, physically and emotionally. I feel like I’ve let a ton of people down.”
Original deal: Seven years, $245 million
Remaining years:
2025: $38 million
2026: $38 million
The good news here: There are only two seasons left. But even though there are longer deals worth more money, no one is getting less bang for their buck than the Angels for Anthony Rendon. The third baseman who was among the toasts of the 2019-20 free-agent class has never played more than 58 games in a season for the Angels. This past season he hit a grand total of zero home runs in 206 at-bats. FanGraphs had him as a negative WAR player for the first time in his career.
Worse, Rendon’s not-so-subtle disinterest leaves almost no room for hope. Rendon will be paid handsomely, and eventually the Angels will be able to move on from what will go down as one of the worst contracts in MLB history.
Might that day be coming sooner rather than later?
“When Anthony has played, he hasn’t been productive,” Angels general manager Perry Minasian said in September. “He’s going to have to come in and earn it. There are no handouts. We’re starting to create some depth. … The best players are going to play.”
Honorable mention
José Berríos, Toronto Blue Jays: Four years, $86.9 million remaining, with an opt-out after 2026
Robbie Ray, San Francisco Giants: Two years, $50 million remaining
Lance McCullers Jr., Houston Astros: Two years, $35.4 million remaining
DJ LeMahieu, New York Yankees: Two years, $30 million remaining
Jung Hoo Lee, San Francisco Giants: Five years, $105.2 million remaining, with an opt-out after 2027
Jordan Montgomery, Arizona Diamondbacks: One year, $22.5 million remaining
Starling Marte, New York Mets: One year, $20.75 million remaining
(Top photo of Anthony Rendon and Mike Trout: Kevork Djansezian / Getty Images)
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