At the time, these contracts had everyone scratching their heads. The dollar signs were eye-popping, the term lengths were wild, and the reactions ranged from “overpaid” to “career-ending mistake.”
But hindsight has a way of flipping the narrative. Whether it was championships, MVP seasons, or culture-shifting impact, these deals aged better than anyone could’ve predicted. Here are 20 sports contracts that went from laughable to legendary.
20. Alex Rodriguez – Texas Rangers (2001)
Ten years, $252 million felt like Monopoly money back in 2001. Even though the Rangers didn’t win big with him, A-Rod’s production more than justified the groundbreaking contract.
19. Drew Brees – New Orleans Saints (2006)
Brees came to New Orleans with a bum shoulder and a lot of doubts. All he did was turn the franchise around and deliver a Super Bowl.
18. Patrick Mahomes – Kansas City Chiefs (2020)
Half a billion dollars? Really? Turns out the Chiefs got a bargain for the most dominant quarterback of his generation.
17. Max Scherzer – Washington Nationals (2015)
Seven years and $210 million seemed excessive for a pitcher on the wrong side of 30. Then he won two Cy Youngs and a World Series while becoming a franchise icon.
16. Kobe Bryant – Los Angeles Lakers (2013)
Kobe’s two-year, $48.5 million extension raised eyebrows as he recovered from injury. But it allowed the Lakers to honor a legend while selling out arenas every night.
15. Joe Montana – Kansas City Chiefs (1993)
Bringing in an aging Montana felt risky, but he brought instant legitimacy to a floundering franchise. He didn’t win a title, but he made them matter again.
14. David Beckham – LA Galaxy (2007)
People scoffed at the $250 million package to bring Beckham to the MLS. Then he changed the league forever, raising its profile globally and opening the door for stars to follow.
13. Bryce Harper – Philadelphia Phillies (2019)
Thirteen years felt excessive for a player some called overrated. He went on to win an MVP and deliver clutch postseason heroics that won the city over.
12. Tom Brady – Tampa Bay Buccaneers (2020)
He was 43 and supposedly washed. Then he won a Super Bowl in year one and reminded everyone never to doubt Tom Brady.
11. Russell Wilson – Seattle Seahawks (2015)
At the time, making Wilson the highest-paid player in the league felt like a reach. But he backed it up with MVP-caliber seasons and deep playoff runs.
10. Miguel Cabrera – Detroit Tigers (2014)
Extending Cabrera for $248 million seemed risky given his age. But he delivered batting titles, home run milestones, and Hall of Fame consistency.
9. Sidney Crosby – Pittsburgh Penguins (2007)
Crosby’s 12-year deal looked like a gamble on long-term health. Instead, it locked up the face of the franchise through multiple Stanley Cups.
8. Stephen Curry – Golden State Warriors (2012)
Four years and $44 million were seen as a reach for an injury-prone guard. That deal became one of the greatest bargains in NBA history as Curry rewrote the game.
7. Giannis Antetokounmpo – Milwaukee Bucks (2020)
Five years, $228 million made small-market fans nervous. Then Giannis delivered an MVP and a championship, proving he was worth every cent.
6. Albert Pujols – St. Louis Cardinals (2004)
Before the Angels deal, the original seven-year, $100 million contract with St. Louis paid off in MVPs, dominance, and a title. Vintage Pujols was worth the price.
5. Peyton Manning – Denver Broncos (2012)
Neck surgeries made this contract a major risk. Two Super Bowl appearances and a win later, the Broncos looked pretty smart.
4. Derek Jeter – New York Yankees (2001)
Ten years and $189 million for the Captain felt like sentiment over value. Then he continued to produce, win rings, and stay the face of the franchise.
3. Lionel Messi – FC Barcelona (2017)
Leaked reports of a $674 million deal blew minds. But Messi kept delivering at a historic pace, making it hard to argue with the return.
2. Shohei Ohtani – Los Angeles Angels (2018)
At the time, $2.3 million seemed steep for an unproven two-way player from Japan. Turns out it was the greatest value contract in sports history. Too bad they lost him to their city rival.
Read More: 10 Reasons the Kansas City Chiefs Are the NFL’s Most Hated Team
1. LeBron James – Miami Heat (2010)
The Decision came with a massive payday and massive backlash. Then came four Finals appearances, two titles, and one of the most dominant runs in NBA history.
Read More: 15 NBA Stars Who Landed Massive Contracts but Fell Short of Expectations
