With Roger Federer following Williams into retirement and Rafael Nadal winding down his career, opportunities abound for young players—on and off the court.



When Holger Rune&nbsp;started watching Rafael Nadal, he was about 7, maybe 8, growing up in Denmark and worshiping the Spanish tennis legend for what Rune calls his “fighting spirit.” Then he started looking up to Roger Federer, for his elegance and his transition game coming to the net.



“If I was going to idolize them, I was trying to idolize them all the way. So I wore the same clothes; I played with the same racket,” Rune tells&nbsp;Forbes, confirming that the mimicry extended to wearing Federer’s signature bandana. “I even tried the one-handed backhand, but luckily my coach told me to stick to your own tennis.”



Rune’s tennis has taken him pretty far—onto practice courts with both Nadal and Federer and into competitive matches against another player he has long admired, world No. 2 Novak Djokovic, whom Rune has actually beaten in two of their three meetings. His game has also sent the 20-year-old skyrocketing to No. 4 in the world rankings, from outside the top 100 at the start of 2022.



And he is not tennis’ only precocious player. A fellow 20-year-old, Carlos Alcaraz of Spain, sits atop the ATP Tour’s rankings while 22-year-old Jannik Sinner of Italy and 24-year-old Casper Ruud from Norway are seen as real contenders to win a Grand Slam, whether at this year’s U.S. Open or going forward.



On the women’s side, Polish phenom Iga Swiatek is No. 1 and owns four major titles at age 22, and American Coco Gauff is a 19-year-old rising star who reached the French Open final last year and won the two biggest tournaments of her career this month.



To be sure, no one—whether tournament organizers or broadcast executives or sponsors—is racing to chase Federer, who retired last year, or Nadal, who has said 2024 will likely be his final season, out of the sport. And while Djokovic is 36 and less than a year younger than Nadal, he continues to play at the highest level, winning titles at this year’s Australian Open and French Open and losing to Alcaraz in a thrilling five-set final at Wimbledon. Still, there is a recognition that tennis tends to go through cycles of talent—just as Pete Sampras and Andre Agassi ruled the era before the Big Three—and there is a growing belief that a new generation is ready to fill the void, on and off the court.



“For sure, it’s not the worst time to be in tennis,” Rune says with a smile.



He and his fellow prodigies have quite the tennis shoes to fill. Djokovic has won a record 23 major singles titles, followed by Nadal with 22 and Federer with 20—no other man has won more than 14 (Sampras). Add it all up, and the Big Three have captured 65 of a possible 80 Slams dating to Federer’s first title at Wimbledon in 2003. Their dominance has been so absolute for so long that tennis pundits speak of a “lost generation,” and the numbers back that up: Players younger than Djokovic have won a combined six Grand Slam titles since Federer exploded on the scene, with four of them coming in the last three years (Dominic Thiem in 2020, Daniil Medvedev in 2021 and Alcaraz in 2022 and 2023).



And while she did not have as much company at the top of the sport, Serena Williams, who like Federer&nbsp;<a href="https://www.forbes.com/sites/brettknight/2022/08/09/serena-williams-tennis-retirement-net-worth-earnings/">announced her retirement</a>&nbsp;last year before backtracking somewhat in subsequent interviews, herself piled up 23 major singles titles, a women’s record for tennis’ Open Era.



The four tennis legends have an equally imposing legacy off the court. A mainstay near the top of&nbsp;Forbes’&nbsp;annual list of the&nbsp;<a href="https://www.forbes.com/lists/athletes/">world’s highest-paid athletes</a>, the 42-year-old Federer is one of&nbsp;<a href="https://www.forbes.com/sites/mattcraig/2022/06/12/billion-dollar-ballers-these-athletes-tiger-woods-lebron-james-federer-messi-ronaldo-mayweather-have-earned-more-than-1-billion-apiece/">just seven athletes</a>&nbsp;with career pre-tax earnings over $1 billion, having cultivated a sponsor portfolio filled nearly top to bottom with premium brands, including Rolex, LVMH and NetJets. “Novak, he tried to be ahead in technology, and Nadal, he just tried to be a little bit different,” Lisa Delpy Neirotti, associate professor of sports management at George Washington University, notes of two players who have crossed $500 million in career earnings. Meanwhile, Williams, who made an estimated $440 million across her career, was a trailblazer among athletes as a&nbsp;<a href="https://www.forbes.com/sites/kurtbadenhausen/2019/06/03/inside-serena-williams-plan-to-ace-venture-investing/">venture investor</a>&nbsp;and a&nbsp;<a href="https://www.forbes.com/sites/kerryadolan/2022/12/08/serena-williams-feels-your-pain/">startup founder</a>, and transcended the sport into mainstream pop culture, appearing in two Super Bowl commercials in 2023 alone.



Alessandro Barel Di Sant Albano, who represents Gauff at Team8 and has worked with Federer, says Williams and the Big Three “have been the GOATs that have taken the traditional TV-watching fan into thinking about athletes as brands. They’re the pioneers that have taken us to a new way of looking at tennis as more of an entertainment platform, and more than just a sport.”



And all of that is setting aside the societal changes of the last 20 years, starting with the rise of social media. The upshot: The players coming of age today are entering a dramatically different, and increasingly global, sponsorship market, with more brands looking to spend more money on tennis than ever before.



The players have already started to take advantage of sponsorship opportunities, with&nbsp;<a href="https://www.forbes.com/sites/brettknight/2023/08/25/the-worlds-highest-paid-tennis-players-2023/">eight of the sport’s ten highest-paid</a>&nbsp;now under 30. Shoe and apparel companies typically come calling first—often by age 13, Delpy Neirotti notes—but other brands have also seen “a unique opportunity to align themselves with someone who can carry the torch,” says Marijn Bal, Ruud’s agent at IMG. “They know that if they get in early, they can get a lot of bang for their buck.”



So what will it take for a young player to reach the heights that Federer did? It starts with winning, which brings more attention from marketers and can also come with a direct payoff because endorsement deals often carry bonuses—sometimes in the seven figures—for climbing up the rankings or winning Grand Slams. For instance, Emma Raducanu raked in $18 million from endorsements and appearances in 2022, after winning the 2021 U.S. Open as a virtual unknown, and Naomi Osaka’s four major titles helped her eclipse Williams’ earnings record for a female athlete with at least $50 million off the court in both 2021 and 2022.



But “you need continued dominance—you can’t be dominant for just a few months, or a couple of years,” adds John Tobias, an agent at GSE Worldwide. “And it’s also about staying healthy in a really physically demanding sport—basically an 11-month-a-year sport that requires an insane amount of travel, an insane amount of dealing with time zones. Then you have to have the right personality and the right, we say,&nbsp;passport—or you come from the right country—and the ability to communicate with people on a global scale.”



Authenticity remains another important factor, which Bal says starts with “don’t endorse Coca-Cola when you’re drinking Pepsi” but extends to aligning with brands that fit the image you’re trying to cultivate for yourself—the way that Federer made himself synonymous with luxury and Nadal cast himself as a rebel.



In addition, “social responsibility and cause marketing are more important now than they ever were before,” says Joe Favorito, a veteran marketing consultant and former executive with the WTA Tour and the U.S. Tennis Association. While the great Arthur Ashe was once questioned for talking about social issues, Osaka’s support for the Black Lives Matter movement and her statements about&nbsp;<a href="https://www.forbes.com/sites/brettknight/2021/06/02/naomi-osaka-is-the-highest-paid-female-athlete-ever-and-her-french-open-exit-may-actually-help-her/">mental health</a>&nbsp;have made her even more valuable for brands, Favorito says.



Even with all of those boxes checked, there is no guarantee anyone will follow Federer to $1 billion in earnings. Players have to be willing to commit to their off-court endeavors, even amid the grind of the tennis schedule—and the teenaged Gauff, for instance, is taking a slow and steady approach as she develops as a player and a person. The 25-year-old Osaka, meanwhile, was once pegged as a perennial champion but has taken an unexpected detour over the last couple of years because of injuries and a recent pregnancy. “The story arc is never that simple because that’s real life,” says Stuart Duguid, who represents Osaka at Evolve, the talent agency they cofounded. “Life happens.”



Still, the number of talented players hitting their primes at once means exciting times ahead for the sport—and, presumably, for their wealth advisors.



“They all push each other, and they’re all friendly with each other,” Bal says. “[Ruud] got to Toronto early—he practiced with Medvedev, with Rune and with Sinner three consecutive days. So these guys are not shy, they’re playing with each other, they’re pushing each other, and it’s great for the sport.”

Western & Southern Open – Day 8

Tennis’ Big 3 And Serena Won 88 Majors And Made $2.5 Billion. A New Generation Is Ready For Their Shot.

Miami Open 2019 – Day 3

The Highest-Paid Tennis Players 2020: They Are Barely Playing, But The Top 10 Pros Still Earned $340 Million

Roger Federer has landed the top spot on&nbsp;<a href="https://www.forbes.com/athletes/">the annual&nbsp;Forbes&nbsp;list of the highest-paid athletes</a>&nbsp;for the first time this year with $106.3 million in pre-tax earnings. The Swiss ace is the first tennis player to take the No. 1 rank since the list debuted in 1990.



Federer’s haul includes $6.3 million in prize money and $100 million from endorsements and appearance fees, lifting him from the No. 5 spot he held in 2019 and beating his previous high of second place in 2013.



“His brand is pristine,” says David Carter, a sports business professor at USC’s Marshall School of Business, “which is why those that can afford to align with him clamor to do so.”



Federer’s endorsement portfolio is unmatched among active athletes, with 13 brands including Barilla, Moet &amp; Chandon and Rimowa paying between $3 million and $30 million to associate themselves with the 20-time Grand Slam champ. The 38-year-old and golfer Tiger Woods are the only two active athletes to have hit $100 million in a single year from sponsorships alone.



Federer’s on-court résumé is the stuff of legend, with the men’s records for most Slam titles and most weeks ranked No. 1 (310). The consistency is staggering. He ranked in the top three for 750 straight weeks—almost 15 years—and qualified for 18 out of 19 Slam finals between 2005 and 2010.



Call it the Jordan playbook, the blueprint for global domination chronicled in ESPN’s ten-part documentary on the basketball great, The Last Dance: command a sport with a global audience for years; appeal to both men and women; stay out of trouble; add in a dose of swagger and a dash of charisma. It made Michael Jordan the <a href="https://www.forbes.com/sites/kurtbadenhausen/2020/04/17/the-inside-story-of-how-michael-jordan-became-the-worlds-richest-athlete/">richest athlete on the planet</a> and the first billionaire athlete. Even in retirement, he continues to <a href="https://www.forbes.com/sites/kurtbadenhausen/2020/05/03/michael-jordans-1-billion-nike-endorsement-is-the-biggest-bargain-in-sports/">collect endorsement checks</a> rivaling those of Federer and Woods thanks to <a href="https://www.forbes.com/sites/kurtbadenhausen/2019/08/28/the-nbas-richest-shoe-deals-lebron-kobe-and-durant-are-still-no-match-for-michael-jordan/">his massive cut of Nike Jordan Brand sneaker sales</a>.



The three breathe a rarefied air, reserved for the most elite competitors. Jordan had the No. 1 spot on the&nbsp;Forbes&nbsp;list six times during his 13-year career with the Chicago Bulls, eventually giving up the mantle to Woods after he retired from the Bulls in 1998. (Formula One’s Michael Schumacher held the crown for two years between Woods and Jordan.) Woods went on to collect more than $100 million annually off the course at his peak, landing at the top of&nbsp;Forbes’ highest-paid athlete ranking a record 12 times until he broke stride, landing in hot water over an infidelity scandal while injuries contributed to a decade-long majors title drought on the links.



Federer, while seizing the top spot late in his career, is showing no signs of slowing down. His latest partnership is with Swiss startup running shoe On, whose headquarters sit close to the new home the tennis star is building on Lake Zurich. A renowned sneakerhead, Federer will endorse the brand, whose sales have been <a rel="noreferrer noopener" href="https://www.oregonlive.com/business/2020/01/on-the-fastest-growing-sneaker-company-youve-never-heard-of.html" target="_blank">doubling annually since its 2010 launch</a>, and also invested in the company in return for an equity stake that one source called “significant,” a partnership that could have serious upside for Federer.



Another sign of his command of the off-court side hustle: Once companies align themselves with him, they almost never leave. Rolex, Credit Suisse, Mercedes-Benz and Wilson have all been on Team Fed for more than a decade. The exception? Jordan’s Nike.



Federer stunned the tennis world in 2018 when he split from the sneaker giant after 20 years and joined with apparel brand Uniqlo. The chain, part of Fast Retailing, made an offer he couldn’t turn down, promising $300 million over ten years whether he was playing tennis or not and leaving open a slot for a shoe deal like the one with On since the Japanese giant doesn’t make sneakers.



The length and terms of the deal raised eyebrows given that Federer was about to turn 37 when he signed it. At that age, almost all tennis players have long since retired—a detail that meant little to the long game the retailer is eyeing.



“We feel the greatest impact of Roger Federer is yet to come,” says Uniqlo’s head of global creative John Jay. “Of course, it will be fueled by his status as the greatest of all time, but Roger’s ability to bring positive change to the world is his future and ours.”



The company hopes Federer can hold the same kind of appeal Jordan still has long after he launched his last jump shot. Already, tennis clubs in Europe are flooded with kids wearing “RF” hats, the logo that Nike controlled for two years after the split but is back in Federer’s hands and is the foundation for future licensing deals.



It wasn’t his only shrewd move. Federer took more control of his brand when he left the IMG sports firm with longtime agent Tony Godsick to launch their own operation in 2013, dubbed TEAM8. Current clients include male tennis pros Juan Martin del Potro and Alexander Zverev, 16-year-old rising star Coco Gauff and New York Rangers goalie Henrik Lundqvist. TEAM8 also found success with the creation of a new annual event, the Laver Cup, which matches a team from Europe versus the rest of the world in a competition that is comparable to golf’s Ryder Cup.



Federer has other levers in the sport that even Jordan doesn’t have. He is a hot commodity for organizers of smaller tournaments that pay appearance fees for top players to show up; a men’s event without one of the Big Three—Federer, Rafael Nadal and Novak Djokovic—is a tough sell. Federer commands the top rate of more than $1 million per stop. Then there are the exhibition tours—a mix of tennis and show business—in places that have no major event to offer. He did a five-stop swing through Latin America in November that added more than $15 million to his bank account, including a match versus Zverev in a bullfighting stadium in Mexico City that attracted 42,517 fans, a record to watch a tennis match.



Federer has used his platform and cash to focus on educating children in Africa, with his namesake foundation spending $52 million to aid 1.5 million kids. He’s teamed with Bill Gates in charity matches three times; the&nbsp;<a href="https://www.forbes.com/sites/tracywang/2020/02/04/bill-gates-doubles-up-with-tennis-legend-roger-federer-for-much-anticipated-charity-match-in-south-africa/#5a2c77e41b92">latest “Match for Africa”</a>&nbsp;featured Gates and Federer versus Nadal and&nbsp;The Daily Show&nbsp;host Trevor Noah in South Africa, where Federer’s mother was born. The February event raised $3.7 million.



Federer is the GOAT, both on and off the court.



&#8211;<a href="https://www.forbes.com/sites/kurtbadenhausen/">Kurt Badenhausen</a>, Forbes Staff, <a href="https://www.forbes.com/sportsmoney">SportsMoney</a>

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Roger Federer Tops World’s Highest-Paid Athletes: Tennis Ace Scores First No. 1 Payday With $106 Million

Doubles match full view – Christiaan Kotze

An Evening When The Stars Descended With Racquets: Federer And Nadal Faced-Off On African Soil For The Mother Of All Tennis Matches

Roger Federer,&nbsp;Novak Djokovic&nbsp;and&nbsp;Rafael Nadal&nbsp;are kicking off play at the U.S. Open as the three favorites to win the title and take home a Grand Slam-record $3.85 million payday as the singles champion. The Big Three are a good bet, having captured 53 out of 63 Slams since the start of 2004, including the last 11.



The on-court dominance has produced a combined $373 million in career prize money for the trio, light years ahead of their peers. But the money off the court is even sweeter for Federer, Djokovic and Nadal, to the tune of a cumulative $1.2 billion during their careers from endorsement partners and appearance fees.



Federer is the highest-paid tennis player for the 14th straight year, with $93.4 million from prize money, endorsements and appearance fees in the 12 months ending June 1. It is a record tally by a tennis player.



READ MORE | <a rel="noreferrer noopener" aria-label="Inside Serena Williams’ Plan To Ace Venture Investing (opens in a new tab)" href="https://www.forbesafrica.com/woman/2019/06/05/inside-serena-williams-plan-to-ace-venture-investing/" target="_blank">Inside Serena Williams’ Plan To Ace Venture Investing</a>



His sponsor portfolio is unmatched in sports, with a dozen partners together paying him more than $60 million a year, well ahead of other global sports icons like&nbsp;Tiger Woods,&nbsp;LeBron James&nbsp;and&nbsp;Cristiano Ronaldo. 



Credit Federer’s long run at the top—his Slam titles span 15 years—and the strong demographics of tennis fans, who spend heavily on equipment, apparel, cars, watches and financial services. The global nature of the sport also allows brands to use the players in marketing around the world.



Federer turned 38 this month, and Father Time will catch up at some point, but Japanese apparel brand Uniqlo is&nbsp;betting $300 million&nbsp;that Federer will continue to resonate with fans long after he hangs up his racket. 



READ MORE | <a href="https://www.forbeswomanafrica.com/wealth/2019/08/26/business-is-booming-for-tennis-ace-naomi-osaka-on-track-to-be-the-highest-paid-female-athlete/" target="_blank" rel="noreferrer noopener" aria-label="Business Is Booming For Tennis Ace Naomi Osaka, On Track To Be The Highest-Paid Female Athlete (opens in a new tab)">Business Is Booming For Tennis Ace Naomi Osaka, On Track To Be The Highest-Paid Female Athlete</a>



After two decades with Nike, Federer signed a ten-year deal with Uniqlo last year that is guaranteed whether he is playing or not. In the coming months, Federer will also likely take back control of his RF logo, which stayed with Nike after their split.



After a two-year Slam drought, Djokovic has roared back to capture four of the past five majors. The titles helped push his 12-month earnings to $50.6 million, including $30 million off the court from appearances and sponsors Lacoste, Head, Asics, Seiko, NetJets and Ultimate Software. He ranks as the second-highest-paid tennis player.



Rounding out the top five players are&nbsp;Kei Nishikori&nbsp;($37.3 million), Nadal ($35 million) and&nbsp;Serena Williams&nbsp;($29.2 million).



Tennis is the only major sport in which women and men are in the same zip code in terms of earnings. The U.S. Open was the first Slam to offer equal payouts for the men’s and women’s events, and now each of the four Slams has equal pay. While Williams was the only woman to crack&nbsp;Forbes&#8216; 100&nbsp;highest-paid athletes&nbsp;this year, the top ten earners in tennis are split evenly between men and women.



The top ten collectively made $312 million,&nbsp;up 23% from last year, fueled by huge gains by Federer, Djokovic and&nbsp;Naomi Osaka. See the full top ten below.



<h3 class="wp-block-heading">10. Sloane Stephens</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1142602393/960x0.jpg?fit=scale" alt="Mutua Madrid Open Masters v day 7"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $9.6 million



Prize money: $4.1 million



Endorsements: $5.5 million



The 2017 U.S. Open champion returns to Flushing Meadows this year&nbsp;wearing a tennis shoe&nbsp;based on the “Aqua” colorway of Nike’s retro Air Jordan VIII. Her Nike pact, which began last year, is one of the biggest in the sport. Stephens recently announced her engagement to soccer star Jozy Altidore.



<h3 class="wp-block-heading">9. Simona Halep</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1163387350/960x0.jpg?fit=scale" alt="The Championships - Wimbledon 2019"/><figcaption>CORBIS VIA GETTY IMAGES</figcaption></figure>



Total earnings: $10.2 million



Prize money: $6.2 million



Endorsements: $4 million



Halep has won only one event in 2019, but it was a big one: Wimbledon, and its $3 million payday, her second career Grand Slam title. The Romanian pro counts Nike, Wilson, Mercedes-Benz and Hublot among her sponsors.



<h3 class="wp-block-heading">8. Angelique Kerber</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1158622069/960x0.jpg?fit=scale" alt="Nature Valley International - Day Four"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $11.3 million



Prize money: $5.3 million



Endorsements: $6 million



Kerber triggered lucrative bonuses from sponsors, namely Adidas, with her 2018 Wimbledon title and year-end rank of second in the world. In addition to Adidas, the German pro has also renewed deals with SAP, Generali and NetJets since Wimbleon and recently inked a new pact with Procter &amp; Gamble’s Head &amp; Shoulders brand. Other endorsements include Yonex, Porsche, Rolex and Lavazza.



<h3 class="wp-block-heading">7. Alexander Zverev</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1160486313/960x0.jpg?fit=scale" alt="Rogers Cup Montreal - Day 8"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $11.8 million



Prize money: $6.3 million



Endorsements: $5.5 million



The 22-year-old German is a rising star on the ATP Tour and has 11 career titles, including the 2018 year-end ATP Finals, which was worth $2.5 million in prize money. He has a large deal with Adidas, in addition to endorsements with Head, Peugeot, Richard Mille and Zegna.



<h3 class="wp-block-heading">6. Naomi Osaka</h3>



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Total earnings: $24.3 million



Prize money: $8.3 million



Endorsements: $16 million



Osaka will see her endorsement number soar even higher, having signed a series of deals since her 2018 U.S. Open win. The biggest is with Nike, which was inked just ahead of our June 1 cutoff and is worth an estimated $10 million annually. She also recently added a series of endorsement partners—Hyperice, BodyArmor and Muzik—where&nbsp;she received equity stakes&nbsp;in the businesses.



<h3 class="wp-block-heading">5. Serena Williams</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1160435948/960x0.jpg?fit=scale" alt="Rogers Cup Toronto - Day 6"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $29.2 million



Prize money: $4.2 million



Endorsements: $25 million



The world&#8217;s&nbsp;highest-paid female athlete&nbsp;four years running had a record year off the court after her return to tennis following the birth of daughter Olympia. She added deals with Pampers, Axa Financial and General Mills to her roster.&nbsp;Williams&#8217; next act is&nbsp;tackling venture investing, focused largely on companies led by women or people of color.



<h3 class="wp-block-heading">4. Rafael Nadal</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1161098596/960x0.jpg?fit=scale" alt="Rogers Cup Montreal - Day 10"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $35 million



Prize money: $9 million



Endorsements: $26 million



The Spaniard is one of the biggest draws in tennis and can command appearance fees of more than $1 million a pop. His primary sponsors include Nike, Babolat, Kia Motors, Telefónica, Richard Mille and Mapfre.



<h3 class="wp-block-heading">3. Kei Nishikori</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1160287842/960x0.jpg?fit=scale" alt="TENNIS: AUG 07 Coupe Rogers"/><figcaption>ICON SPORTSWIRE VIA GETTY IMAGES</figcaption></figure>



Total earnings: $37.3 million



Prize money: $4.3 million



Endorsements: $33 million



Nishikori and Zverev are the only non-Slam winners among the ten highest-paid tennis players. But Nishikori&#8217;s robust endorsement portfolio is fueled by his status as the most successful Japanese player ever. He is set to be one of the faces of the 2020 Olympic Games in Tokyo. His sponsors Asahi, NTT, Japan Airlines, Lixil, Procter &amp; Gamble and Nissin are all official Olympics partners.



<h3 class="wp-block-heading">2. Novak Djokovic</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1168302451/960x0.jpg?fit=scale" alt="Western &amp; Southern Open - Day 6"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $50.6 million



Prize money: $20.6 million



Endorsements: $30 million



There have been ten tennis seasons in which a player won more than $12 million in prize money. Djokovic owns seven of those years. His $135 million in career prize money has him $9 million ahead of Federer. Djokovic&#8217;s Lacoste endorsement is one of the richest deals in the sport.



<h3 class="wp-block-heading">1. Roger Federer</h3>



<figure class="wp-block-image"><img decoding="async" src="https://specials-images.forbesimg.com/imageserve/1161645059/960x0.jpg?fit=scale" alt="Day Eleven: The Championships - Wimbledon 2019"/><figcaption>GETTY IMAGES</figcaption></figure>



Total earnings: $93.4 million



Prize money: $7.4 million



Endorsements: $86 million



In addition to his blockbuster Uniqlo pact, Federer added a multimillion-dollar deal with Rimowa last year. The luggage brand joined Credit Suisse, Mercedes-Benz, Rolex, Moet &amp; Chandon, Barilla and others in Fed&#8217;s endorsement stable.



-Kurt Badenhausen; Forbes

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The Highest-Paid Tennis Players 2019: Roger Federer Scores A Record $93 Million

Besides family, South African restaurateur Yente Pienaar shares something else in common with world tennis legend Roger Federer.
And that is the word ‘serve’, which she does well in her restaurant, far from the flashy center courts of Wimbledon.
A second cousin to Federer, 29-year-old Pienaar owns and runs the Meet on Milner restaurant on Milner Street in the heart of Waterkloof in South Africa’s capital Pretoria.
On any given day, the place is teeming with locals and diplomats – few know she is related to tennis’ numero uno.
“I wouldn’t say people come here because of who I am related to. Like only some people know we are second cousins. I have only seen [Roger Federer] twice. He has never been here but my aunt and uncle [his parents] have a couple of times,” says Pienaar.
Multi-faceted, as a young student, she won entrepreneur of the year at her high school, the Saint Mary’s Diocesan School for Girls, Pretoria. Today, she has the drive and savvy to compete with any man in the restaurant business.
Meet on Milner is a sophisticated meeting place covered floor-to-ceiling with art, bringing to life the quiet, sleepy street and neighborhood it is located in.
<a href="http://www.forbesafrica.com/woman/2017/09/14/from-pizzas-to-pizzaz/" target="_blank" rel="noopener">From Pizzas To Pizzaz</a>
Born and raised in Kwaggafontein, in South Africa’s Mpumalanga province, Pienaar combined her love for cooking, fashion and photography to start her restaurant at the age of 25.
“My mom hated cooking. In the evenings, we would have a choice between toasties or avo on toast. So I got really fed up, and would trade my McDonald’s for cucumber sandwiches. Then I just started making my own food and then later started my own herb garden,” says Pienaar.
This love for cooking continued into her high school years. Pienaar was never one to settle for the ordinary, she would always use her skills to make life better and brighter.
“Even though I went to a nice boarding school, the food could get boring, so I always [enhanced] my food by buying stuff from Pick n Pay. I would always have extra stuff so people would come to me and say, ‘please, like spice up my dish’.”
With an upbringing that advocated imagination and a go-getter’s attitude, Pienaar had dreams and the zeal to fulfill them.
“I always knew when I was small that I wanted to be the editor of Vogue and I wanted to have a restaurant. Those were the two things on my list. So I have got a restaurant now, and it’s been four years,” says Pienaar.
Next on her list is to be an editor, and she is determined.
“I went to TUKS where I studied visual communications. I didn’t really know what I wanted to do but I knew I wanted to go into the arts field. Then I did my honors in drama and film, and that’s another thing I really like and I would like to make a film one day. Creative art directing is what I like.”
The same passion Federer has for the racket, she has for the ladle.
Her restaurant is an amalgamation of two outlets that were earlier a tea room and a 75-year-old pharmacy.
“When I was working at a guest house, I would always drive by the tea room and think this was just a great location.
“I came here with my mother and told her there was such potential. Then I spoke to my parents and told them that I don’t know how this all works, could they help me with a loan, and then they said they would see,” says Pienaar.
It took Pienaar two visits before she could strike a deal with the owners of the tea room. At first, the price was too high and Pienaar left with no deal but she was not ready to give up.
As she traveled back and forth to work daily, she could see the shop was getting emptier attracting fewer customers. It was then Pienaar went to put her offer on the table again.
After being persistent, the owners of the tea room finally gave in to her offer and she began the renovation process.
With the help of her parents, she started her restaurant.
“They are like my bank, my interest-free bank,” she says.
However, Pienaar was not done. After opening up Meet on Milner, she asked the owner of the chemist next door to sell her his store if he ever retired.
“I thought he would retire in maybe two or three years but he came back to me about five months later and told me he is ready to retire. I was shocked and I sure wasn’t ready financially but I knew I wanted the space, and so did many other people, so I bought it.”
<a href="http://www.forbesafrica.com/woman/2017/08/04/pots-pans-passion/" target="_blank" rel="noopener">Pots, Pans And Passion</a>
Meet on Milner attracts the residents of Waterkloof and diplomats from the embassies nearby.
“The food and the service are just different from other restaurants. Your meal always looks different from the last one you had which makes it taste like a new experience every time,” says Beau van Zyl, one of the regulars here.
“I love how the staff takes time to know us, even Yente. And as you can see they even have linen table cloths which you just don’t see anymore,” adds Claudia Dalebout, another regular customer.
Pienaar now plans on incorporating more theme events at the restaurant, such as ‘singles mingle’, as she met her boyfriend here. And then some.
“I love Johannesburg and I would love to expand into Johannesburg. Maybe the next year or so, I could have a ‘Meet on…’ on any street,” adds Pienaar on her future plans.
“I guess the next challenge for me is to become the editor of Vogue. I think Africa needs a Vogue, don’t you?” she says, with a smile.
More hits than misses, Pienaar seems to be making all the right moves.  &#8211; Written by Keketso Majoe

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