It’s the age-old MLB tradition: throw a giant bag of money at a player and hope it doesn’t explode in your face. Sometimes it works out beautifully, but other times, that contract starts to smell bad before the ink even dries.
Whether it was injuries, underperformance, or just a complete failure to mesh with the team, these 17 franchises watched their mega-deals turn into mega-mistakes. Let’s take a look at the biggest “why did we do that” moments in recent baseball contract history.
17. Colorado Rockies – Kris Bryant
The Rockies gave Kris Bryant a massive deal and then spent the next two years pretending it never happened. Between injuries and underwhelming play, it’s been a bizarrely quiet era for a guy once seen as a cornerstone.
16. Chicago Cubs – Jason Heyward
They paid Heyward for defense and leadership, which was code for “we hope he figures out how to hit again.” Spoiler: he never really did.
15. Los Angeles Angels – Josh Hamilton
The Angels took a gamble on Hamilton’s upside and immediately watched it nosedive. Off-field issues and on-field struggles made this a nightmare contract almost from day one.
14. New York Mets – Jason Bay
Bay looked like a slugger in Boston, but once he landed in Queens, the bat vanished. Mets fans were left wondering if they had signed the right guy or just someone with the same name.
13. San Diego Padres – Eric Hosmer
Hosmer got paid like a franchise player and played like a league-average first baseman. San Diego tried for years to make it work before finally moving on.
12. Arizona Diamondbacks – Madison Bumgarner
They paid for playoff magic and got a whole lot of regular-season mediocrity. It never clicked in the desert, and the D-backs were stuck holding the bill.
11. Philadelphia Phillies – Jake Arrieta
The Phillies hoped Arrieta would be their ace, but instead got a lot of grumbling and injuries. He was a shell of his Cy Young self, and the contract didn’t come close to paying off.
10. Detroit Tigers – Jordan Zimmermann
Detroit opened the wallet expecting a reliable starter, and Zimmermann never delivered. His ERA ballooned while his availability plummeted.
9. Boston Red Sox – Carl Crawford
Crawford was supposed to be a game-changer in Boston, but instead, he just looked uncomfortable the entire time. Injuries, inconsistency, and media pressure made this a quick disaster.
8. Texas Rangers – Shin-Soo Choo
Choo put up decent numbers here and there, but never lived up to the size of the paycheck. Rangers fans spent most of the deal waiting for it to end.
7. New York Yankees – Jacoby Ellsbury
Ellsbury went from Red Sox hero to Yankees ghost. The injuries piled up, and he became more myth than man by the end of his deal.
6. Chicago White Sox – Yasmani Grandal
The White Sox made him the highest-paid catcher in team history, and then watched him hit like a backup infielder. Not quite the veteran impact they were hoping for.
5. Miami Marlins – Wei-Yin Chen
Miami handed Chen a surprising pile of cash, then watched him get shelled every fifth day. By the end, they were paying him not to pitch.
4. Baltimore Orioles – Chris Davis
This one was brutal. The Orioles bet on power and instead got strikeouts, slumps, and one of the worst contracts in MLB history.
3. San Francisco Giants – Barry Zito
Zito’s deal was massive and instantly became the standard for “overpaid pitcher” jokes. Even when he was decent, it never felt like enough for the price tag.
Read More: 20 Sports Contracts That Looked Crazy — Until They Paid Off
2. Los Angeles Angels – Albert Pujols
Pujols put up some solid counting stats, but he wasn’t the machine L.A. thought they were buying. The back half of that contract felt like a very expensive farewell tour.
Read More: Ranking the 20 Most Self-Certain Pitchers Ever
1. New York Mets – Bobby Bonilla
Yes, we’re still talking about it. Bonilla’s deferred money masterpiece is the cautionary tale to end all cautionary tales—he’ll be cashing checks long after most of us retire.
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