Every offseason, MLB teams dream of making the one big move that puts them over the top. They throw piles of money at superstar free agents, hoping for MVP numbers, October magic, and jersey sales galore.
But sometimes, those dreams turn into nightmares faster than you can say “designated for assignment.” Whether it was age, injuries, bad vibes, or just plain underperformance, these 20 superstar signings were supposed to be franchise-changers—and they weren’t.
20. Troy Tulowitzki – Toronto Blue Jays
Toronto hoped Tulowitzki would bring his Colorado magic north of the border. Instead, he brought injuries and a steady decline.
19. Josh Hamilton – Los Angeles Angels
Hamilton’s Texas numbers earned him a massive payday, but he never looked comfortable in Anaheim. Off-field struggles and on-field slumps defined his Angels tenure.
18. Barry Zito – San Francisco Giants
Zito crossed the Bay with a Cy Young and a $126 million contract. What followed was inconsistency, bloated ERAs, and a lot of second-guessing.
17. Pablo Sandoval – Boston Red Sox
Boston brought in the Panda, hoping for postseason magic. What they got was weight issues, injuries, and a shocking lack of production.
16. Carl Crawford – Boston Red Sox
Crawford was electric in Tampa Bay but looked like a completely different player in Boston. Injuries and pressure derailed him almost immediately.
15. Jason Bay – New York Mets
Bay arrived in Queens with big power expectations and left with barely a whisper. Citi Field swallowed his swing and his confidence.
14. Jacoby Ellsbury – New York Yankees
The Yankees paid Ellsbury to be their next dynamic star. Instead, he spent more time on the IL than on the field, collecting checks and dust.
13. Mike Hampton – Colorado Rockies
Hampton famously signed with Colorado “for the school system.” The real lesson? Don’t give a finesse pitcher a mega-deal to pitch at Coors Field.
12. Chris Davis – Baltimore Orioles
Davis had monster power and a monstrous contract to match. Then his bat completely vanished, and he became the face of dead money in baseball.
11. Prince Fielder – Texas Rangers
Fielder was supposed to be the centerpiece of Texas’s lineup, but neck issues cut his career short. The contract aged poorly, even though the player didn’t get a fair shot.
10. Mo Vaughn – Anaheim Angels
Vaughn was a monster in Boston, but injuries and underwhelming play followed him to Anaheim. The only thing that stayed consistent was his paycheck.
9. Vernon Wells – Los Angeles Angels
The Angels took a huge swing trading for Wells and his massive contract. He never found his rhythm and became one of the most expensive flops of the decade.
8. José Reyes – Miami Marlins
The Marlins went big with Reyes as part of their flashy 2012 reboot. The whole experiment blew up a year later, and Reyes was leaving.
7. Kei Igawa – New York Yankees
The Yankees thought they were getting the next big thing from Japan. They got a guy who couldn’t stay in the majors and never adjusted to MLB hitters.
6. Eric Hosmer – San Diego Padres
Hosmer was paid like a cornerstone piece but never met the hype. His production plateaued quickly, and fans grew restless with every ground ball to second.
5. Miguel Cabrera – Detroit Tigers (Post-Prime Years)
Miggy was a legend, but that contract extension lasted way too long. Detroit paid premium prices for healthy, below-average production in his twilight years.
4. Jeff Bagwell – Boston Red Sox (Trade Regret)
Okay, technically not a signing, but the Red Sox letting Bagwell go before he blossomed in Houston was a front-office nightmare. Boston gave away a superstar before he became one.
3. Robinson Canó – Seattle Mariners
Canó was still productive in Seattle, but not nearly enough to justify his monster deal. Add in a PED suspension, and the Mariners were left with major buyer’s remorse.
Read More: Ranking the Most Overpaid Baseball Players in MLB History
2. Yoenis Céspedes – New York Mets
The Mets re-signed Céspedes after his 2015 heroics, but he spent most of his contract sidelined. From wild boar injuries to disappearing acts, it was a wild and disappointing ride.
Read More: 20 MLB Stars Who Signed Massive Contracts and Never Delivered
1. Alex Rodriguez – Texas Rangers
Texas made A-Rod the wealthiest man in sports history, and he delivered big numbers, but the team didn’t win, and the deal crushed their payroll. It was a one-person show that never translated to team success.
Read More: The 15 Worst Free-Agent Contracts in MLB History
