Now, the Serbian – who will return to the top of the world rankings after his first-round win at the US Open last week – has wrested the title of this year’s highest-paid tennis player from 20-time Grand Slam champion Roger Federer.
Djokovic, 36, has netted about $38.4 million over the past 12 months before taxes and agents fees, according to Forbes magazine.
He has earned $13.4 million from prize money and an estimated $25 million from endorsement deals.
Not far behind is Wimbledon champion Carlos Alcaraz, who took second place on Forbes’s list.
The 20-year-old Spaniard has earned an estimated $31.4 million over the past 12 months, including $11.4 million in on-court earnings and an estimated $20 million off the court.
Carlos Alcaraz wins men's Wimbledon final – in pictures
Third on the list is Iga Swiatek, who won two Grand Slams in the past year and is now the women’s No 1 player both on court and off it. She earned $22.4 million last year, Forbes estimates, including $8.4 million in prize money.
The calculation does not include players who have retired, such as Federer and Serena Williams. However, both remain among the world’s highest-paid athletes.
Federer’s annual income was estimated at $95 million in May, buoyed by more than a dozen brand endorsements, including a recent partnership for RF-branded sunglasses with eyewear company Oliver Peoples.
Williams, the only woman among the world’s top 50 highest-earning athletes, earned an estimated $45.3 million in the 12 months to May, largely from endorsements with brands including Nike and Michelob Ultra.
Djokovic has now earned more than $510 million over the course of his career.
He has a net worth of about $240 million, according to wealth tracking website Celebrity Net Worth.
As of June this year, he holds the record for all-time career earnings in prize money. The ATP reports that he has earned $172 million in pre-tax income since he turned professional 20 years ago.
While he is well ahead of Rafael Nadal ($134.6 million) and Federer ($130.6 million), those numbers do not account for inflation and bigger prizes in recent years.
In addition to his income from tennis, Djokovic has endorsed several brands over his career, including adidas, Uniqlo, Mercedes-Benz, Seiko and Lacoste.
Under the company Family Sport, he also runs a business empire with his parents and younger brothers, including restaurants and catering businesses, and has organised the Serbia Open in previous years.
He holds private equity in a handful of companies. In January, he made a reported seven-figure investment in Austrian beverage start-up waterdrop.
Last year, Reuters reported that the tennis player took an 80 per cent stake in QuantBioRes, a Danish biotech company that has been working on a vaccination-free cure for Covid-19.
He owns properties in Serbia, Spain, Monte Carlo, New York City and Miami.
Indian comedian and YouTuber Bhuvan Bam has a net worth of 1.2 billion Indian rupees ($14.7 million), according to calculations by the country's CNN-News18 television channel.
Bam's major income sources include YouTube advertisements and his web series. His BB Ki Vines channel has 26.3 million subscribers and has amassed 4.7 billion views since its launch in 2015.
Bam, 29, started out as a musician before turning his hand to comedy. He has lampooned TV reporters and covered teenage life and family issues. The YouTuber has since created series for Disney+ Hotstar and Amazon miniTV.
Bam, who lives in New Delhi, has endorsed or featured in advertisements for Pizza Hut, eyewear retailer Lenskart and male grooming brand Beardo.
He also has a line of merchandise, including T-shirts, caps and shoes, for sale on Youthiapa.com.
Tunisian tennis star Ons Jabeur has invested in the North Carolina Courage women’s football team, becoming a minority investor. The investment amount was not disclosed.
Ranked No 5 in the world, Jabeur is the second professional tennis player to invest in the club after Naomi Osaka in 2021.
“Soccer and female empowerment are my main passions outside of tennis. When Naomi took an equity stake in the Courage, I asked her if she would give me a starting position as a striker, but she said no,” Jabeur said on August 31.
“So I did the next best thing and became an owner. The Courage are the perfect club for me in terms of shared values and ambitions, both on and off the field.”
The Courage completed a successful equity raise recently. While the club did not disclose how much it raised, media reports estimated it at $15 million.
The club’s majority owner is Welsh-American businessman Steve Malik.
Watch: Tunisian Ons Jabeur to head to Wimbledon final again
Jabeur, 29, has a net worth estimated at $5 million, according to Celebrity Net Worth. She is the highest-ranked and most accomplished African and Arab player in WTA and ATP history.
She has earned $11.58 million in prize money since turning pro in 2010. Her on-court earnings to September 1 total $2.39 million, the WTA said.
Jabeur has endorsed several major brands, including Lotto, Wilson, Qatar Airways, Qatar National Bank Tunisia, Tunisie Telecom, Maximilian Jewellery and consulting company Talan.
Her success offers brands a way to reach the African and Arab markets.
Jabeur earned $6.5 million in total earnings over the course of 2022, according to estimates by Forbes.
American designer Tom Ford has purchased former US first lady Jackie Kennedy’s childhood residence in the East Hamptons for $52 million.
He purchased the property from media producer David Zander, who bought it in 2018 for $24 million.
The transaction was reported by The Wall Street Journal.
The New York property, known as Lasata, an Algonquian word meaning “place of peace”, once belonged to Kennedy’s paternal grandfather John Vernou Bouvier.
As a child, Jacqueline Bouvier spent her summers on the estate.
Other owners include fashion designer John Krakoff and his interior designer wife Delphine Krakoff.
The 10-bedroom, 13-bathroom home sits on a 2.8-hectare compound that includes a two-bedroom guesthouse, pool house, caretaker’s cottage and three-car garage with a workshop.
A portion of the grounds has been redesigned by French landscape architect Louis Benech.
Ford has been credited with revitalising Gucci. This year, Estée Lauder Companies became the sole owner of his eponymous label in a deal that valued the total enterprise at $2.8 billion.
The Texas native, 62, has a net worth estimated at $2.5 billion, according to calculations by Forbes.
He is a prolific investor in art and collects works by Andy Warhol, Alexander Calder, Ellsworth Kelly and Lucio Fontana.
In December, Ford bought another home in Palm Beach, Florida, which he has since traded with private equity chief executive Brian Kosoy for a different estate in South Florida, according to the real estate website The Real Deal.