A native of Calcutta, Paes is about to participate in his seventh Olympic Games -- a record for any tennis player.
His streak trails back to Barcelona in 1992, a pre-internet era when cell phones were hardly portable and headlines were dominated by basketball's original Dream Team featuring Michael Jordan and Charles Barkley.
Although times have changed, the 43-year-old Paes is still chasing medals for India.
"Like my dad says, you've got to be a little bit crazy to play in seven Olympics," Paes tells CNN's Open Court, crediting the consistency of his supporting cast for his longevity. They include his yoga master of 26 years, his fitness coach of 23 years and his hitting coach of 19 years.
"Age is just a number," he adds. "What drives me is passion. Passion to be everything I can be."
Paes has won a staggering total of 18 grand slams in men's doubles and mixed doubles. As a testament to his staying power, he's partnered with both Martinas: First Martina Navratilova, with whom he won the Australian Open and Wimbledon in 2003; and more recently Martina Hingis, with the pair sweeping all four grand slams.
But there's one event that has eluded him so far. Although Paes earned a bronze playing singles in Atlanta at the 1996 Games -- where he shared the podium with gold medalist Andre Agassi -- he's yet to win medals in either doubles category.
"I've already got a singles medal in my bag, so I really strive to win a doubles medal and put them side-by-side," he says.
Paes will partner 36-year-old Rohan Bopanna in the men's doubles. Whatever friction that existed between the two in the past has evidently been swept aside in the name of national unity.
Bopanna had previously elected not to partner with Paes at London 2012.
Bopanna will also be playing with India's female tennis star Sania Mirza, leaving Paes out of the mixed doubles competition.
Paes is a rare breed: an Indian who makes his living as an athlete outside of cricket and badminton. "To go out and represent 1.3 billion Indians at the pinnacle of my sport is something that's a great honor," he said.
Paes got his first dose of Olympic fever at a very young age, cherishing his father's bronze medal from playing field hockey for India at Munich '72.
It was during those Games -- which were marred by a terrorist attack
-- that Leander was conceived, he says.
"So really I am an Olympic kid. I was born in June 1973, so nine months later ..."
"For me it's a humbling experience to come from a second generation Olympic family," he explains. "To grow up with that and see (my father's) medal and see his Olympic jerseys that he used to play field hockey for India ... I used to iron those jerseys before matches.
"So I grew up with that pedigree. My mom captained Indian basketball as well so I used to iron her jerseys for India."
Although Paes came in third in Atlanta, the fact that he earned a medal for India takes it to the top of his career achievements on a personal level.
"It's on my bedside in a little safe," he says of his own bronze medal. "I look at it every day when I'm home. I'm dead serious."
Paes was able to share his Olympic triumph in Atlanta with his father in the stands, a memory which has not faded over the past 20 years.
"I remember when the last ball flew over my head and went out," he says. "I just turned to my dad, and it was a very special moment between father and son.
"My dad is my greatest hero. I've always looked up to him, I always want to emulate him as a man, as a father, as a person and as an athlete."
It's the belief that hard work pays off which mattered most to his father, a lesson his son has taken to heart.
"The legacy I would like to leave behind once I retire is that with a lot of hard work and belief in myself that any human being can achieve their goals. I'm not the tallest man in the world. I'm not the most talented tennis player ... so if I can do it I'm sure everyone who believes in themselves can do it," Paes says.
That legacy will come to fruition in Rio, win or lose.
"I always wanted to be an Olympian," says Paes, who had the honor of waving India's flag at the opening ceremony of Sydney 2000.
"I'm really looking forward to the opening ceremony," he says, excitedly. "To walk into the opening ceremony knowing that it's a world record for any tennis player playing seven Olympics ... it will be magical."