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.
1Michael Jordan x NikeThe 1984 deal that created Air Jordan and turned a rookie guard into a footwear empire.
2David Beckham x AdidasA 2003 lifetime agreement with Adidas, reported around $160 million, that set the template for modern athlete branding.
3LeBron James x NikeSigned out of high school in 2003 and converted into a lifetime deal in 2015 reported at over $1 billion.
4Lionel Messi x AdidasThe Argentine's long-running Adidas partnership, built around signature boots worn through four World Cups.
5Cristiano Ronaldo x NikeA Nike relationship that began at Sporting and became a lifetime deal in 2016.
6Tiger Woods x NikeThe 2000 renewal worth a reported $105 million, then the largest endorsement contract in sport.
7Stephen Curry x Under ArmourThe 2013 signing that gave Under Armour a basketball line and Curry his own sub-brand.
8Serena Williams x NikeA tennis partnership that ran for two decades and put her catsuits and tutus on Grand Slam courts.
9Shaquille O'Neal x ReebokThe 1992 rookie deal behind the Shaq Attaq, later abandoned so he could sell cheap shoes at Walmart.
10Derrick Rose x AdidasA 13-year, $185 million agreement signed in 2012 — briefly the biggest in sports.
11Rory McIlroy x NikeThe 2013 golf deal reported at around $250 million, signed the year he switched every club in his bag.
12Caitlin Clark x NikeThe WNBA guard's Nike deal, which produced her first signature shoe, the Caitlin 1, in 2026.
13James Harden x AdidasA 2015 defection from Nike reported at $200 million that gave Adidas its marquee NBA signature line.
14Roger Federer x UniqloThe 2018 apparel switch away from Nike, reported at $300 million over ten years.
15Allen Iverson x ReebokA 1996 deal, later made lifetime, whose Question and Answer models defined basketball street style.
16Kobe Bryant x NikeThe 2003 move from Adidas to Nike that produced the low-cut Kobe line copied across the league.
17Simone Biles x AthletaThe 2021 switch from Nike to Athleta, chosen for the gymnast's say over how she was marketed.
18Naomi Osaka x NikeA 2019 signing that made her one of the sport's highest-paid endorsers before she turned 22.
Comments 1
Signed in 1984 with a rookie Bulls guard, answered in 2003 with a footballer's lifetime deal; the newest entry ships this October at $140: https://youpick.best/articles/nike-vs-adidas-ranked https://youpick.best/articles/shaquille-oneal-ranked-many-ways
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