MLB's 9 Biggest Nightmare Contracts by 2028: Who Will Regret These Deals? (2026)

Imagine a future where some of baseball's biggest stars become financial burdens for their teams. It's a reality that's closer than you think, as we project the 9 most nightmare-inducing MLB contracts by 2028. But here's the twist: it's not just about the money; it's about the value these players will (or won't) bring to the table. And this is the part most people miss: even the brightest stars can fade, leaving teams with hefty bills and dwindling returns.

As the MLB landscape evolves, with players like Kyle Tucker and Bo Bichette potentially signing decade-long, nine-figure contracts, we can't help but wonder: which current megadeals will age like fine wine, and which will turn into costly mistakes? To answer this, we delve into the world of contract data, focusing on cash owed, including deferred payments, as per Spotrac. Surprisingly, there are already 24 players set to earn at least $100 million from 2028 onward. But will they all be worth it?

Some players, like Roman Anthony, Garrett Crochet, and Vladimir Guerrero Jr., are young enough to still be in their prime by 2028, making their contracts seem like safe bets. However, others, like Julio Rodríguez, face convoluted contract options that could complicate their future. And then there's the controversy: players like Mookie Betts and Shohei Ohtani, whose contracts include substantial deferred payments, raising questions about their long-term value.

Take Betts, for instance. By 2028, he'll be 35, still owed $235 million, with an additional $120 million in deferred payments stretching into the 2040s. Similarly, Ohtani will be 33, with $692 million still due. Is this a wise investment, or a recipe for disaster? The Dodgers, already boasting multiple World Series titles, might have the revenue to stomach these payments, but what about teams like the Diamondbacks, who threw $210 million at Corbin Burnes? If Burnes doesn't regain his dominant form, the next 11 years could be brutal.

As we explore these contracts, from Austin Riley's declining performance to Aaron Judge's injury-prone history, one thing becomes clear: the future is uncertain. Players like Willy Adames, Mike Trout, and Corey Seager face questions about their ability to maintain productivity into their mid-30s. Meanwhile, pitchers like Max Fried and Trea Turner must overcome the odds stacked against aging shortstops and pitchers.

But the real controversy lies in the top spots: Manny Machado and Xander Bogaerts. Machado, despite his hitting prowess, has become a liability at third base, while Bogaerts has already seen a sharp decline since signing his mega-deal. Are these contracts the worst in the sport? We invite you to join the discussion, as we ponder the fine line between investing in talent and overpaying for past glory. Will these players prove their worth, or will their contracts become cautionary tales for teams and fans alike?

MLB's 9 Biggest Nightmare Contracts by 2028: Who Will Regret These Deals? (2026)

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