The Tokyo Olympics have proven to be one of the most durable events in all of sports. The Summer Games were nearly canceled in 2020, but the expensive and time-consuming decision to postpone them for a year instead eventually won the day. Then they were almost canceled again as a coronavirus resurgence forced a state of emergency — but here, too, Tokyo 2020 survived.
Now, the long-awaited 2020 Games are set to begin — albeit with no fans in the stadiums.
Those who place in the top three spots in their respective contests will go home with lots of spending cash. According to Team USA, gold medals come with a reward of $37,500, $22,500 for silver and $15,000 for bronze. For those who learn how to make their skills, talent and celebrity pay, however, that’s only the beginning of a lifetime of fortune and riches. Here’s a look at the wealthiest Olympians of all time.
Lee Chong Wei
A giant of the sport of badminton, Lee Chong Wei won silver medals in three of his four Olympic appearances between 2004-2016. He retired in 2019 after being diagnosed with cancer, but not before he was ranked No. 1 in the world for 349 weeks, including a streak of 199 weeks straight.
The source of his wealth is not exactly clear, but he enjoyed some of the biggest sponsorships in badminton during the peak of his career, according to RepublicWorld, including deals with Samsung, 100Plus, Yonex and Cafe 99.
Before there was Usain Bolt, the man whose name was synonymous with speed was Carl Lewis. The greatest American track-and-field star since Jesse Owens, Lewis is one of only four athletes to have won nine gold medals, including four in Los Angeles in 1984, two in Seoul in 1988, two in Barcelona in 1992 and one in Atlanta in 1996. He is regarded as one of the greatest athletes of the 20th century and one of the greatest Olympians of all time.
He successfully crossed over to movies and TV, piling up 10 acting credits and 75 TV and film appearances as himself. He recently added the Silk alternative milk brand to his endorsement portfolio.
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American figure skating great Brian Boitano competed in the 1984 Olympics in Sarajevo and the Lillehammer Olympics a decade later in 1994, but it was at the 1988 Olympics in Calgary where he struck gold.
He remained a prominent name in skating through the decades as a performer, judge, host and representative of the United States in overseas competitions. Mostly, he found a second career as a TV personality, racking up nearly 80 appearances, including 14 episodes of his own Food Network show “What Would Brian Boitano Make?”
Ukraine native Oksana Baiul was a world champion figure skater at the age of 15. One year later, she won gold at the Lillehammer Olympic Winter Games in 1994. Pulling glory out of a painful beginning, Baiul was raised by figure skating — literally. Her mother — the last living member of her family — died when she was 13, leaving the young future champion alone. Her father figure coach left for Canada shortly after.
In 2012, Baiul made headlines again — this time off the ice. She sued her management agency, claiming that they collected millions of dollars on her behalf without her knowledge. Her suit claimed that her representation misled her at the height of her career, when she signed contracts as an orphaned minor who didn’t speak any English.
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The biography on Mark Spitz’s own website refers to him as “the most famed athlete of all-time.” While that’s up for debate, the nine-time gold medalist and 11-time Olympic medalist is without question one of the greatest athletes ever to enter Olympic water. At the 1972 Munich Olympics, Spitz became the first Olympian to win seven golds in seven events with seven world records, according to Team USA.
His miracle in Munich landed him a $50,000 poster deal, according to The Hollywood Reporter. Norman Brokaw of the William Morris Agency quickly arranged $5 million more in endorsement deals, making Spitz one of the original pioneers of big-money Olympic endorsements. He was still getting endorsement deals into the 2010s and he also earns money as a speaker and an investor.
Before there was Lance Armstrong, there was Jan Ullrich, a German cyclist who spent the 1990s piling up white jerseys at the Tour de France. At the 2000 Sydney Olympics, Ullrich won a gold medal and a silver medal in the road race and time trial, respectively. He’s considered one of the sport’s greatest-ever time trialists.
Ullrich was hounded by doping allegations that eventually led to his retirement in 2007, according to CyclingTips. The scandal was the catalyst for the sport-wide scandal that would eventually consume Armstrong as well. Ullrich survived to land several endorsement deals, but by the mid-2010s, he began to spiral downward into a series of highly publicized personal problems, allegations of hard drug abuse, a drunk driving incident, and eventually, two arrests in two weeks for violent alleged assaults involving drugs and alcohol.
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Belgian Eddy Merckx was considered the greatest cyclist of all time long after his appearance at the Tokyo Olympics in 1964. The winner of more than 500 major races, Merckx has too many records to name. His five Tour de France wins were the most ever until Lance Armstrong won seven before his doping disqualifications.
Merckx was so dominant that by 1972, he had deals with Gillette, Adidas and other big brands. He was such a sensation in the media that he was a millionaire making $400,000 a year by age 27.
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Longtime Bruins captain Ray Borque remains history’s greatest offensive defenseman — he owns the records for career scoring, assists and points by a defenseman to this day. Bourque repped his native Canada in the 1998 Olympics in Nagano.
Although he was inducted into the Hall of Fame during his first year of eligibility and remains one of the only players to have his number retired by two different teams, he didn’t appear to land major endorsement deals. After more than two decades in Boston, he signed one last contract with the Avalanche for $5.5 million for a single season, according to ESPN.
Figure skater Tara Lipinski took home gold at the 1998 Games in Nagano. At just 13 years old in 1996, Lipinski qualified for the United States team at the world championships. Just one year later she shocked the world when she became the youngest world champion in the history of the sport. When she edged out Michelle Kwan in Nagano, she became the youngest skater to win gold in an individual event at just 15 years and 255 days old, according to Olympics.com.
She went on to a successful career in television, racking up nearly 20 credits as an actress and more than 100 credits as a host, broadcaster, interviewer and guest.
Scott Hamilton was the most dominant skater in the world — winning four consecutive World Championships — between his first trip to the Olympics in 1980 at Lake Placid and his second visit to the games in Sarajevo in 1984 when he took home the gold.
He made his celebrity and talent pay in his post-Olympic career, first becoming a professional skater and joining the Ice Capades. Later he formed his own show company, which would become Stars on Ice. He’s also worked as a skating analyst and a broadcaster. A cancer survivor and a champion, Hamilton has used his incredible life story to find success as a motivational speaker, as well.
Although he didn’t know it at the time, the crash that brought down Peter Sagan’s cycle at the Tour de France would also bring down his dreams of Tokyo gold. The three-time world champion announced he will miss the 2020 Olympics after receiving surgery for an infection in his knee that started with the crash. It would have been the Slovakian’s third trip — he pedaled through the 2012 Olympics in London as well as the 2016 games in Rio. With 113 professional wins, he is one of the sport’s all-time elites.
He launched his own brand, the Peter Sagan Line of apparel accessories. According to CyclingTips, he’s a master at using social media to amplify his sponsorship brands, sometimes earning hundreds of thousands of dollars with a single Facebook post.
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British track and field giant Alan Pascoe earned a silver medal at the Munich Games in 1972, but he also competed in Mexico City in 1968 and Montreal in 1976. One of the first athletes to capitalize on the business of athletics in the U.K., Pascoe became a pioneering sports marketer. He created Alan Pascoe Associates Ltd., which then went through several name changes, according to AthleticsWeekly. A broadcaster, businessman and celebrity endorser, he earned tens of millions of dollars, but he raised tens of millions more for sports and for charity.
In 1986, Greg LeMond became the first American and non-European in general to win the Tour de France — his first of three titles. No American has legitimately won the Tour since. Although he never competed in the Olympics, LeMond makes this list because he was chosen for the U.S. Olympic team in 1980, but America boycotted the Moscow Games. After that, he went pro and the Olympics didn’t allow professionals to compete until after he retired in 1996. He is the greatest American cyclist in history.
LeMond was one of the first prominent figures in cycling to raise allegations that his heated rival Lance Armstrong might be taking performance-enhancing drugs. His LeMond Bicycles company has become one of the most respected names in the sport since he launched the brand in 1986. In February, Forbes reported that he just unveiled a new signature line of LeMond bikes.
Still the most famous and infamous name in cycling, Lance Armstrong fell from revered to reviled, from champion to cheater after he was engulfed in a doping scandal that toppled him from his perch at the summit of the racing world.
In the early 2000s, it was hard to find a human wrist that wasn’t adorned with yellow Livestrong rubber. Armstrong inspired the world when he survived cancer and went on to smash all records with an incredible seven Tour de France wins. By the 2010s, however, Armstrong’s world was crumbling as former teammates began admitting to using banned substances and implicating Armstrong himself. He was eventually banned from racing for life and had all of his titles — including his Tour de France wins — stripped. In 2013, he returned his only Olympic medal, the bronze he took home from Sydney during his glory days in 2000.
Although he’s also a standout skateboarder, snowboarding is what made Shaun White one of the most famous faces in winter sports. He won gold in three of his four Olympic appearances. No snowboarder has ever won more X Game gold medals and total medals than “the Flying Tomato” — he has 15 gold and 23 total X Game medals.
Money.com called him one of the richest winter athletes, citing his impressive real estate portfolio, his many business investments and his corporate endorsements and sponsorships. Those sponsorships were worth $2 million per deal at one point, according to Forbes.
Michael Phelps is to water what Shaun White is to powdery, frozen water — the sport’s greatest champion. But the truth is, Phelps stands alone in the modern era. With 28 medals, he’s the most decorated Olympian from any sport and it’s quite possible that he is the greatest Olympian of all time. His 23 golds are more than double the record of his next-closest rival.
Aside from establishing himself as a prominent advocate for mental health — not to mention the face of the online therapy app Talkspace — he has his own signature swim spa line and made millions from endorsements with Visa, Under Armour and Speedo, just to name a few.
When Usain Bolt was wrapping up his legendary career in 2017, Forbes reported that he was earning more than $32 million a year from his sponsorship deals alone. The supremely marketable Jamaican sprinter was one of the highest-paid athletes in the world thanks to contracts with brands like Advil, Sprint, XM and many others. Puma alone was paying him $10 million a year.
Five years later, and Usain Bolt is still the fastest man alive, according to CNBC — the records he set are all still intact. With eight Olympic medals to his name, Bolt three-peated both the 100-meter and 200-meter in Beijing 2008, London 2012 and Rio 2016.
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Caitlyn Jenner is now most commonly in the news regarding her bid to become the governor of California — but she’s certainly no stranger to the spotlight. In the 1970s, she broke the world decathlon record and won gold in 1976 at the Montreal Games. Jenner also competed at Munich in 1972.
Jenner’s star power was rewarded with big contracts with brands like Wheaties and Coca-Cola. In the 1990s, Jenner earned hundreds of thousands of dollars promoting fitness products with Kris Jenner. Her third act came when she found enormous fame and renewed celebrity stardom with the rise of the Kardashian family as a television, media and marketing juggernaut.
A veteran of both the London 2012 Olympics and the Rio 2016 Olympics, Anna Kasprzak rose to fame as a Danish dressage champion — but that’s not what made her one of the richest millennials in the world, according to Forbes. She is the partial owner of ECCO, the Denmark-based shoe company founded by her grandfather, Karl Toosbuy, in 1962. ECCO is now worth $1.46 billion.
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