The tennis world was stunned when Serena Williams announced that she’d be pulling out of the US Open to finish healing from a hamstring injury, according to Yahoo Sports. Along with her sister, Venus, Williams revolutionized the sport of tennis in the 21st century. The pair ushered in a new era both on the court and in the realm of marketing, branding, endorsements and sponsorships.
Some of the tennis greats who made their talents pay are icons of the sport who have held onto laundry lists of records that have endured for decades. Others were known less for their athletic prowess and more for their impact on culture and in the media.
All, however, are famous across the world and rich beyond imagination. Meet the biggest names in tennis who earned the biggest bucks during and after their time on the court.
Anyone with even a passing familiarity with tennis knows the name Chris Evert. After playing in her first Grand Slam tournament in 1971 at the age of 16, Evert went on to win 18 Grand Slams singles titles (tied for fifth-best in women’s history) and play in the finals of 34. Evert holds a big record over every tennis player who has ever picked up a racket, male or female — her astonishing .900 winning percentage (1,309-148).
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Famous for her over-the-top grunting as much as for her devastating two-hand forehand, Monica Seles was part of the supremely talented and highly marketable crew of teen phenoms that emerged in the 1990s. Known as the Youth Brigade, according to the International Tennis Hall of Fame (ITHOF), the group included stars like Jennifer Capriati. Seles went pro at just 15 years old in 1989, the year she won her first tournament after beating none other than a retiring Chris Evert.
Billie Jean King
One of the greatest feminist icons of tennis, sports and history in general, Billie Jean King will always be famous for beating Bobby Riggs in the “Battle of the Sexes” in 1973. Across the world, 93 million people tuned in to watch King win three straight sets. Beyond that one exhibition match, however, King was a giant of the sport, winning 39 Grand Slam titles including 20 Wimbledon titles.
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According to the ITHOF, Billie Jean King herself called Martina Navratilova “the greatest singles, doubles, and mixed doubles player who ever lived.” Navratilova holds enough both-gender records to back up that statement and then some. No male or female player has ever won more than her 167 singles tournaments, 177 doubles events or 2,189 matches. Her career began in 1975 and ended with her winning the mixed doubles championship at the US Open a month before she turned 50 in 2006. In that three-decade span, she lost just 219 times in singles matches.
Martina Hingis entered one of the most saturated fields in the history of women’s tennis during the talent glut of the late 1990s. The roster included the likes of Jennifer Capriati, Monica Seles, and Steffi Graf, according to ITHOF. Even so, Hingis emerged as a talent among talents, winning 114 career titles. The first major title came when she was just 15 years, nine months old with a doubles championship at Wimbledon — she remains the youngest titlist in history.
Simona Halep walked away from Roland Garros in 2018 with her first Grand Slam title, according to Forbes, only to win Wimbledon the following year in 2019. One of the biggest names in the sport, she’s been ranked No. 1 twice between 2017 and 2019.
The No. 4 highest-paid female athlete of 2020, Halep earned $10.9 million last year, according to Forbes, $6.9 million on the court and $4 million from endorsements. She also has a real estate portfolio that includes ownership of a hotel at a ski resort in her native Romania.
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Although he went pro in 2000, Andy Roddick had his breakout year in 2003, when he beat Andre Agassi, made it to the semifinals at Wimbledon, and won the US Open, according to the ITHOF. His crushing power had a lot to do with his 32 career singles titles. His 152-mph serve remains the fastest ever recorded in a Grand Slam tournament.
During her run of dominance that spanned the 2010s, Caroline Wozniacki played in epic battles against the era’s greats like Simona Halep, Kim Clijsters and the Williams sisters. She went pro in 2005 at the age of 15. Wozniacki was also consummately marketable, with Forbes naming her among the 10 highest-paid female athletes as early as 2011 and consistently after that throughout the decade. She retired at the beginning of 2020.
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In 2000, Forbes reported on a great, but not elite tennis player who was ranked No. 9 in the world and had never won a title. Nonetheless, she was one of the most famous and highest-earning female athletes on Earth across all sports despite having earned just six-figure winnings on the court the year before. It was Anna Kournikova, whose name at the peak of her success was one of the most popular image searches across all of Google. Her model looks, trendy outfits and designer dog helped her ride an early-internet wave to self-branding superstardom.
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By the time she announced her retirement in 2014, Li Na was enduring hundreds of injections per week into her knee, which had been operated on four times, to alleviate the relentless swelling, according to Forbes. She had been a global superstar since 2011, when she became the first Asian-born player to win a Grand Slam singles event at the French Open. Her status earned her $2 million a year off the court thanks to multimillion-dollar, multiyear deals with Nike, Mercedes-Benz and Samsung.
The arrival of Venus Williams and her sister Serena signaled the end of the Stefi Graf era and the beginning of a new time for tennis where physical power and athleticism ruled the day. One half of the greatest sister act in sports history, Venus Williams has 21 Grand Slam wins, 49 single title wins and 22 doubles titles — with Serena, of course. Off the court, she’s a force as well, according to Forbes, having launched her own interior design brand and her own apparel brand before buying an ownership stake in the Miami Dolphins.
Although he’s best remembered for his famously cantankerous personality, it was John McEnroe’s velvety soft touch at the net that earned him so much of his on-court success. His rivalries with Ivan Lendl, Jimmy Connors and Björn Borg were the stuff of legend, according to the ITHOF. He ended his career with 155 career titles, 17 major championships and more than 1,400 wins. McEnroe was a member of the Davis Cup team 12 times.
Steffi Graf was ranked No. 1 in the world for a cumulative 377 weeks, a feat unmatched by any player, male or female, before or since. She spent a record 186 consecutive weeks at No. 1, according to the ITHOF. The most dominant woman of the late 1980s and early 1990s without question, Graf achieved the greatest bragging rights in tennis history when she won the mythical “Golden Grand Slam” in 1988 — that’s when she became the only player ever to win all four Grand Slam singles titles and an Olympic gold medal in the same year. Also, no other player male or female has ever won every Grand Slam tournament at least four times except for Steffi Graf.
In the late 1980s, the male counterpart to Steffi Graf was Andre Agassi — a young, dominant and exciting superstar who came along just when the sport needed one the most. Agassi was so dynamic — both in performance and personality — that Nike signed him to a multimillion endorsement and sneaker deal as a teenager well before he ever won a tournament, according to the ITHOF. He won more than 74% of his major matches and more than 90% of his Australian Open matches. An Olympic gold medalist, Agassi retired with 61 career titles.
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Andre Agassi’s greatest career rival was Pete Sampras, who beat Agassi just 28 days after his 19th birthday to become history’s youngest US Open men’s singles champion. His 14 major championships include seven Wimbledon titles and five US Open titles, both of which put him in a tie for the most of all time for those tournaments. His 14 victories in 18 finals — 78% — represent the best percentage in history. All in all, Pete Sampras won 66 career titles — five more than Agassi.
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When it ranked Maria Sharapova as No. 87 on the list of the world’s richest self-made women in 2020, Forbes estimated her net worth to be $200 million. After a nearly 20-year career, Sharapova retired with five Grand Slam titles, according to Forbes. Along the way, she picked up $39 million in prize money — the third most of all time among women tennis players. Off the court, however, the endorsement powerhouse pulled in $300 million from corporate sponsors and appearances while launching several businesses. Incredibly, she was the highest-paid female athlete in the world across all sports for 11 years straight.
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Rafael Nadal’s 20-year career began in 2001 and he’s still one of the highest-paid celebrities across all trades. He earned $40 million in 2020, according to Forbes, which estimates that his appearance fees are in the seven figures. The Spaniard has won more than $121 million in prize money since his debut two decades ago and has established himself as the greatest clay-court competitor in modern tennis. He passed his 1,000th career win in 2020. His GOAT rivalry with Roger Federer — and now Novak Djokovic — is destined to go down with McEnroe-Borg and Evert-Navratilova as one of the best in history, according to Forbes.
One of the most instantly recognizable women on Earth, Serena Williams earned $94 million in prize money over the course of her career, according to Forbes, more than twice that of any other female athlete in history. Off the court, she has millions coming in from nearly 20 corporate sponsors and investments in dozens of startups through her company Serena Ventures. With 23 Grand Slam singles titles — more than any player in the Open era and second only to Margaret Court — Williams dominated the sport like few other players in history. She won that 23rd title, passing Steffi Graf’s 22, by beating her sister Venus at the Australian Open in 2017.
Novak Djokovic is one-third of the sacred triumvirate that has dominated men’s tennis so thoroughly from Wimbledon 2003 through Wimbledon 2021 that it has its own fraternity — the Big 3. Rafael Nadal, Roger Federer and Djokovic have won 58 of 69 Grand Slam tournaments, according to Statista. Djokovic himself now has 20 Grand Slam titles, tying him with the other two to become the only three men ever to win 20 majors. The Serbian’s $144 million in career prize money is the biggest haul in the history of the sport.
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Which champion among the Big 3 is truly the GOAT on the court depends on who you ask, but the undisputed king of tennis money makers is Roger Federer, whose sponsor portfolio is the envy of the sports world, according to Forbes. He’s currently the No. 7 highest-paid athlete in the world, pulling in $90 million in the year ending June 2021 alone.
He was No. 1 in 2020. His career on-court earnings have topped $130 million, but that’s a pittance compared to the haul he takes home from his corporate deals. His 10-year contract with the Japanese apparel brand Uniqlo alone pays him $300 million. A Swiss company called On, which Federer owns a piece of, will go public this fall.
Roger Federer spent a record 302 weeks at No. 1 and holds the record for Grand Slams singles championships with 20 titles and 30 trips to the finals.
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