The rich keep getting richer in the world of sports. Five months after Canelo Alvarez signed the richest contract in professional sports history with DAZN, MLB phenom Mike Trout bumped Alvarez down to second place with a colossal $430 million extension with the Los Angeles Angels.
Over the course of a few weeks during the wild baseball offseason, Bryce Harper inked the most lucrative contract in baseball history with the Phillies in February…. until the player he hoped would follow him to Philadelphia finalized a deal that could keep in him Los Angeles for the rest of his career.
Here is an updated list of the 20 richest contracts in sports history, starting with Stephen Curry.
20. Stephen Curry: $201.2 million/5 years (2017)
Average Annual Value: $40,200,000
After earning the first unanimous MVP award in NBA history, Stephen Curry became the first player to sign a contract that broke the $200 million mark in 2017.
19. Russell Westbrook: $205 million/5 years (2018)
Average Annual Value: $41,000,000
The 2017 NBA MVP signed a max deal the following year, and while he has yet to deliver in the playoffs, Westbrook has now averaged a triple-double in three consecutive seasons.
18. Zack Greinke: $206.5 million/6 years (2016)
Average Annual Value: $34,416,667
The 2009 AL Cy Young award winner left the Dodgers after the 2015 season and signed a deal with the Diamondbacks that made him the highest-paid pitcher in baseball by AAV.
17. Max Scherzer: $210 million/7 years (2015)
Average Annual Value: $30,000,000
The Nationals lured Scherzer in free agency with a megadeal, and it’s safe to say he’s been worth the money. Scherzer won Cy Young awards in 2016 and 2017, and finished second in Cy Young voting in 2018.
16. Prince Fielder: $214 million/9 years (2012)
Average Annual Value: $23,777,777
The Tigers won the Fielder sweepstakes in 2012, but the slugger would only play two seasons in Detroit before being traded to Texas. Neck injuries ended Fielder’s career in 2017.
15. Clayton Kershaw: $215 million/7 years (2014)
Average Annual Value: $30,714,285
After winning two Cy Young awards in the span of three seasons, Kershaw was rewarded with a monster deal and added a third Cy Young in 2014.
14. David Price: $217 million/7 years (2016)
Average Annual Value: $31 million
David Price helped the Red Sox win the World Series in 2018, going 2-0 against the Dodgers.
13. Joey Votto: $225 million/10 years (2014)
Average Annual Value: $22.5 million
The 2010 NL MVP cashed in with a huge deal in 2014, and has put together back-to-back All-Star seasons in 2017 and 2018.
12. James Harden: $228 million/6 years (2017)
Average Annual Value: $38 million
James Harden has become one of the most polarizing players in the NBA, but it’s hard to argue with his production. The 2018 NBA MVP averaged 36.1 points per game this season.
Tie-10. Albert Pujols: $240 million/10 years (2012)
Average Annual Value: $24 million
The former Cardinals phenom hasn’t quite lived up to his contract in Anaheim, and the Angels have only made one playoff appearance since Pujols arrived.
Tie-10. Robinson Cano: $240 million/10 years (2014)
Average Annual Value: $24 million
Robinson Cano delivered three All-Star seasons for the Mariners before being traded to the Mets in late 2018.
9. Miguel Cabrera: $247 million/8 years (2016)
Average Annual Value: $31 million
Miguel Cabrera won back-to-back MVP awards in 2012 and 2013, but the Tigers likely regret giving Cabrera such a lucrative deal at the age of 33.
8. Alex Rodriguez: $252 million/10 years (2001)
Average Annual Value: $25.2 million
A-Rod took contracts into a new stratosphere in 2001. According to ESPN, three MLB teams had payrolls smaller than Rodriguez’s AAV at the time.
7. Nolan Arenado: $260 million/8 years (2019)
Average Annual Value: $32,500,000
The Rockies locked up their perennial All-Star after he won six consecutive Gold Gloves and four consecutive Silver Slugger awards.
6. Alex Rodriguez: $275 million/10 years (2008)
Average Annual Value: $27.5 million
Rodriguez would only play 99 games or more in six of the ten years on his deal, but he did help power the Yankees to their last World Series title in 2009.
5. Manny Machado: $300 million/10 years (2019)
Average Annual Value: $30 million
The White Sox, Phillies and Yankees were all reportedly in the running for Machado, but the Padres swooped in with a huge offer for the third baseman.
4. Giancarlo Stanton: $325 million/13 years (2014)
Average Annual Value: $25 million
To put Alex Rodriguez’s earlier deals into perspective, Stanton became the first player other than Rodriguez to surpass A-Rod’s 2001 deal in terms of total value. Rodriguez had already broken his own total value record in 2008.
3. Bryce Harper: $330 million/13 years (2019)
Average Annual Value: $25,384,615
It didn’t take long for Phillies fans to start booing Harper in his first season as a Phillie, but he’s committed to playing the rest of his career in Philadelphia. Harper’s deal includes a no-trade clause and no early opt-outs.
2. Canelo Alvarez $365 million/5 years/11 fights (2018)
Average Annual Value: $73,000,000
Mexican superstar Canelo Alvarez inked a massive deal with streaming service DAZN and easily won the first fight of his 11-fight deal against Rocky Fielding last December.
1. Mike Trout: $426.5 million/12 years (2019)
Average Annual Value: $35.54 million
Bryce Harper made it clear that he wanted Mike Trout to join him in Philadelphia, but Trout responded by signing the biggest contract of all time to secure his future with the Angels. Even at $35 million per year, Trout is still considerably underpaid.
