5 of the biggest endorsement deals in modern history

by Nov 18, 2021ENDORSEMENTS & SPONSORSHIP, LISTICLES

Since the 1920s, brands endorsing athletes and vice versa, has become a huge part of sport, with famous pants wearing baseball phenom Babe Ruth’s endorsement of All America Athletic Underwear starting the craze. Whilst athletes in the past may have considered brand endorsements an income supplement, modern-day endorsements are a completely different kettle of fish, a big piping hot pond or even a big boiling ocean of fish in fact (different kettle of fish is a weird phrase). Athletes are now raking in huge amounts of money that dwarf their regular salaries and allow them to retire far earlier than they have any right to.

When Michael Jordan signed a 5-year $7 Million endorsement with Nike in 1984, he set a new bar for the world’s biggest athletes’ endorsement deals, disgusting anti-capitalists everywhere. In the years since, the money continues to rise to levels so sickening that my keyboard was adorned with yesterday’s dinner by the time I’d finished the research for this article. These days, many of the world’s most prolific athletes see most earnings coming from endorsements and brand partnerships. We’ve compiled a list of the top 5 largest modern endorsement deals in sport for you to have a look at.


Lionel Messi – The Face of Adidas

5. Lionel Messi & Adidas

Although he is the second-highest-paid athlete globally and synonymous with football, Lionel Messi is last on our rundown of highest endorsement deals. Poor guy. He has a yearly endorsement income of $27 million, as well as his yearly salary of $80 Million. Messi has been signed to the German sports brand Adidas since 2006 and is considered by many, the face of their brand. Other endorsement deals he has penned include Gatorade, Pepsi, Budweiser, and others. I guess he just really likes drinks (and money).

Athlete: Lionel Andrés Messi

Sport: Football

Team: Paris Saint-Germain F.C (2021-Present)

Brand: Adidas

Endorsement period: 2006 – Present (Lifetime)


4. Roger Federer & Uniqlo

UNIQLO signed a deal with Roger Federer worth a massive $300m

Once synonymous with the brand Nike, 20-time Grand Slam winner and millions-time ball hitter Roger Federer switched to the Japanese designer brand UNIQLO. His endorsement deal with them is worth a whopping $300 million over the next 10 years, almost double what his 20-year endorsement with Nike would have been worth and a smidge under $300 million more than I earn writing sports marketing content. This makes Roger Federer and UNIQLO one of the biggest endorsements deals of the all-time.

Athlete: Roger Federer

Sport: Tennis

Grand Slam Wins: 20

Brand: UNIQLO

Endorsement period: 2020 – 2030


One of sports few billionaires, with help from Nike

3. Tiger Woods & Nike

Part-time Whacky Racer and full-time golfer Tiger Woods is well known for his 2009 infidelity scandal. This infamous ordeal put him off the track to become the first athlete to make a very villainous sounding one billion dollars. His deal with Nike, at the time, was one of the most lucrative deals in history for a pro athlete, and Tiger Woods was one of the most endorsed athletes in the world. Because of that scandal, Woods lost a large number of his endorsements, but at least he was gettin’ some, oh and Nike and EA Sports continued to support his career anyway, which helped.

Tiger Woods continued to work on his golfing career and ended up being one of the highest-paid athletes of all time with a total net worth of over $1.5 Billion. With just 10% of that being his prize money from golfing, you can see how endorsement deals have become the primary income source for sporting GOATs like Tiger. Whoever said cheaters never prosper have never met Tiger Woods or any billionaire ever, I guess.

Athlete: Eldrick Tont “Tiger” Woods

Sport: Golf      

Professional wins: 109

Brand: Nike

Endorsement period: 1996 – Present


2. Cristiano Ronaldo & Nike

Cristiano Ronaldo is, arguably, the most famous footballer on the planet and one of the most recognisable athletes of all time. Many people consider him the face of football, with global influence unmatched by any other athlete or person for that matter (outside of the Kardashian clan and Dwayne Johnson, of course). Ronaldo has a life-long endorsement contract with Nike which has exceeded $1 Billion making him one of the richest Nike-sponsored athletes of all time and set to be footballs first and only billionaire player. Not only does he have endorsements with Nike, but other formidable Brands such as EA Sports and Herbalife. The man is so rich he can afford to buy children, and he did.

Athlete: Cristiano Ronaldo dos Santos Aveiro

Sport: Football

Team: Manchester United (2003-2009, 2021-Present)

Brand: Nike

Endorsement period: 2003 – Present (Lifetime)

Cristiano Ronaldo – Footballs billionaire

1. Steph Curry & Under Armour

Steph Curry signed a behemoth contract with Under Armour

Ranked at No.9 on the Forbes list of the World’s Highest-Paid Athletes of 2019, Steph Curry who currently plays for the Golden State Warriors holds one of the largest shoe endorsement deals of all time. With a $34.9 million annual contract with the Golden State Warriors, his endorsement with Under Armor worth $42 million a year greatly exceeds this. The endorsement between Steph Curry and Under Armor is the fourth-highest endorsement worldwide of any athlete, coupled with this being one of the most expensive annual payments of all time and has landed him at number one on our list.

Athlete: Wardell Stephen Curry II

Sport: Basketball (NBA)

Team: Golden State Warriors (2009-Present)

Brand: Under Armour

Endorsement period: 2013 – 2024


So if you’re interested in offering a blog writer a lucrative endorsement deal, get in touch today to find out what depravity I would stoop to for a million or two. Seriously, though, a well executed endorsement deal can prove instrumental in your brands growth strategy. At Cheat we help brands make the most of their deals, with PR activity and marketing campaigns built around your objectives utilising the faces of your brand. Get in touch today to see how we can support with your next endorsement opportunity.