# The 18 Greatest Athlete Endorsement Deals in Sports History

> Some of these contracts built a shoe empire; others just rented a logo for a season. Eighteen deals, one question of who got the better end.

*By YPB Team · Published August 11, 2026 · https://youpick.best/ranking/the-18-greatest-athlete-endorsement-deals-in-sports-history*

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## Current results (0 votes)

1. **Michael Jordan x Nike**
   The 1984 deal that created Air Jordan and turned a rookie guard into a footwear empire.
2. **David Beckham x Adidas**
   A 2003 lifetime agreement with Adidas, reported around $160 million, that set the template for modern athlete branding.
3. **LeBron James x Nike**
   Signed out of high school in 2003 and converted into a lifetime deal in 2015 reported at over $1 billion.
4. **Lionel Messi x Adidas**
   The Argentine's long-running Adidas partnership, built around signature boots worn through four World Cups.
5. **Cristiano Ronaldo x Nike**
   A Nike relationship that began at Sporting and became a lifetime deal in 2016.
6. **Tiger Woods x Nike**
   The 2000 renewal worth a reported $105 million, then the largest endorsement contract in sport.
7. **Stephen Curry x Under Armour**
   The 2013 signing that gave Under Armour a basketball line and Curry his own sub-brand.
8. **Serena Williams x Nike**
   A tennis partnership that ran for two decades and put her catsuits and tutus on Grand Slam courts.
9. **Shaquille O'Neal x Reebok**
   The 1992 rookie deal behind the Shaq Attaq, later abandoned so he could sell cheap shoes at Walmart.
10. **Derrick Rose x Adidas**
   A 13-year, $185 million agreement signed in 2012 — briefly the biggest in sports.
11. **Rory McIlroy x Nike**
   The 2013 golf deal reported at around $250 million, signed the year he switched every club in his bag.
12. **Caitlin Clark x Nike**
   The WNBA guard's Nike deal, which produced her first signature shoe, the Caitlin 1, in 2026.
13. **James Harden x Adidas**
   A 2015 defection from Nike reported at $200 million that gave Adidas its marquee NBA signature line.
14. **Roger Federer x Uniqlo**
   The 2018 apparel switch away from Nike, reported at $300 million over ten years.
15. **Allen Iverson x Reebok**
   A 1996 deal, later made lifetime, whose Question and Answer models defined basketball street style.
16. **Kobe Bryant x Nike**
   The 2003 move from Adidas to Nike that produced the low-cut Kobe line copied across the league.
17. **Simone Biles x Athleta**
   The 2021 switch from Nike to Athleta, chosen for the gymnast's say over how she was marketed.
18. **Naomi Osaka x Nike**
   A 2019 signing that made her one of the sport's highest-paid endorsers before she turned 22.

Tags: brands, sports, nike, sneakers, adidas