Baseball contracts can be wild. One day, a guy is raking at the plate, throwing heat, or making Gold Glove plays, and the next—after securing a massive paycheck—he’s suddenly swinging at air, losing velocity, or booting routine grounders like he just learned the game. It happens. Teams bet big, and sometimes they lose big.
Let’s take a look at 15 players who secured the bag and promptly… well, let’s just say their teams probably had buyer’s remorse.
1. Chris Davis (Baltimore Orioles)
Davis went from crushing homers to literally setting records for not hitting. His 0-for-54 streak in 2019 was painful to watch, and the Orioles paid him handsomely for some of the worst production in MLB history.
2. Jacoby Ellsbury (New York Yankees)
The Yankees thought they were getting a speedster and on-base machine. Instead, they got injuries, inconsistency, and a guy who vanished so thoroughly by the end of his contract that Yankees fans started conspiracy theories about where he went.
3. Albert Pujols (Los Angeles Angels)
Pujols was a machine in St. Louis. In Anaheim? Not so much. He was still decent, but nowhere near what the Angels were paying for, turning into a shell of his former self pretty quickly.
4. Josh Hamilton (Los Angeles Angels)
The Angels really thought Hamilton would keep mashing like he did in Texas. Instead, he struggled mightily, got hurt, and ultimately left in what felt like a giant waste of cash.
5. Barry Zito (San Francisco Giants)
The Giants expected an ace. They got a No. 5 starter with an ERA consistently above 4.00. The best thing Zito did in San Francisco was help them win a ring after his deal was already a lost cause.
6. Carl Crawford (Boston Red Sox)
Crawford went from a dynamic Tampa Bay superstar to an injury-prone mess in Boston. The Red Sox couldn’t get rid of him fast enough and shipped him to the Dodgers in a massive salary dump.
7. Jason Heyward (Chicago Cubs)
Great defense, sure. But the Cubs didn’t hand out nearly $200 million for a few Gold Gloves. His bat disappeared almost immediately, making his contract one of the worst in franchise history.
8. Stephen Strasburg (Washington Nationals)
Strasburg dominated in the 2019 World Series, got paid, and then… barely pitched again due to injuries. This contract is already looking like a disaster.
9. Prince Fielder (Texas Rangers)
Injuries derailed Fielder’s career fast. Texas got a few okay seasons before a neck injury forced him into an early retirement.
10. Miguel Cabrera (Detroit Tigers)
Miggy is a Hall of Famer, no doubt. But that extension was brutal. The Tigers paid him huge money while his production and health declined rapidly.
11. David Wright (New York Mets)
Wright was a Mets legend, but injuries made this contract an absolute bust. He barely played after signing it, and the Mets were stuck paying for years of rehab.
12. Mo Vaughn (Anaheim Angels & New York Mets)
Vaughn left Boston and immediately fell off a cliff. Injuries and weight issues made this contract a total disaster.
13. Yoenis Cespedes (New York Mets)
Cespedes was electric in his first stint with the Mets, but once he got paid, the injuries piled up, and at one point, he hurt himself… chasing a wild boar?
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14. Rick Porcello (Boston Red Sox)
Porcello somehow won a Cy Young in 2016. After that? He became a liability, and by the end of his deal, Boston was happy to see him go.
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15. Pablo Sandoval (Boston Red Sox)
The Kung Fu Panda turned into an absolute disaster for the Red Sox. He showed up out of shape, played terribly, and was released before his contract even ended.
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