He grew up a few shanked forehands from Madison Square Garden in North Pelham, New York, a scrappy child of the 1930s, but even early on it was clear he belonged in the big arena.
His skills of self-promotion were dazzling; nobody works the room better than he does. And, it must be said, this - and that preternatural golden tan - probably worked against his acceptance in the tennis establishment.
That finally changed forever on Monday when it was announced that 82-year-old Nick Bollettieri will be enshrined in the International Tennis Hall of Fame in Newport, Rhode Island, later this summer.
So, how does it feel?
Bollettieri, sitting courtside for the BNP Paribas Showdown, featuring a Novak Djokovic versus Andy Murray exhibition, pondered the question with uncharacteristic silence. A full five seconds passed before he responded.
"I didn't think it would ever happen," said a clearly moved Bollettieri, who would later tear up when introduced to a supportive crowd. "Speechless? Maybe. That's not something that happens very often."
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Six years ago, ESPN interviewed Jim Courier for a lengthy profile of Bollettieri, who has been involved with the coaching of no fewer than 10 former No.1-ranked players, including Courier.
Bollettieri had recently been described in a Wall Street Journal story as "the most prolific tennis coach in the history of the game".
Courier shook his head. "Right," he said. "Anyone who doesn't think so doesn't know the game. Clive Davis is to music as Nick Bollettieri is to tennis. Clive has an ear for talent - whether it's Aretha Franklin, Stevie Wonder or Mariah Carey. Nick has [made] more tennis players than anyone.
"If he doesn't get into the Hall of Fame soon, it's a joke."
Frankly, he sounded a bit angry.
And now, decades after it probably could - or should - have happened, Bollettieri will be formally recognised for his broad contributions to the game.
He created the first - and, to date, most successful - American tennis factory in Bradenton, Florida. The Nick Bollettieri Tennis Academy, subsequently purchased by International Management Group in 1987, was a boarding school for elite juniors. And the survive-and-advance concept of piling talent on top of talent worked.
"You're 15, 16 years old and you're down there with Andre Agassi, Yannick Noah, Johan Kriek," Courier remembered. "You're a junior, but you're training as a professional.
"It's like the Thomas Friedman book, The World Is Flat. Nick flattened the tennis world in a very Darwinian way. He put together an ecosystem of the world's greatest juniors and sprinkled in some pros as well."
Boris Becker was the first pupil to become No.1, followed by Monica Seles, Courier and Agassi, Martina Hingis, Marcelo Rios and Jelena Jankovic. Serena and Venus Williams have both been Bollettieri students over the years. Maria Sharapova arrived at the academy from Siberia at the age of nine. Fifteen years later, she still lives in Bradenton.
Four of his players preceded him into the Hall of Fame - and just as many are likely to follow him.
Although players must wait until they've been out of the game for five years before they are considered by the Hall of Fame, coaches have no such parameters. That's why it's curious that this took so long. Officially, Bollettieri will go in as a contributor.
My father [James] always told me not to say anything when I wouldn't get into the Hall of Fame," Bollettieri said. "So I didn't. What are you going to gain by that?
"I was just telling my wife and my two adopted children that I think it's God's hand. He had a plan for me. My new book is coming out in April. I guess it's just my time."
Bollettieri said the book will be dedicated to Arthur Ashe and include a forward by Courier. He'll arrive early in Newport to do some clinics and on enshrinement day, Mary Carillo will introduce him.
"I'd like to thank my family, my players and my coaches," Bollettieri said, sounding as though he was already making his acceptance speech.
And then he paused.
"Words cannot express how I feel right now."
This feature originally appeared on ESPN.com