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.

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.