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The Ocean Club, A Four Seasons Resort, Bahamas

  • One Ocean Drive, Paradise Island, Bahamas

Leo Rolle

Tennis Pro/Director
“Everybody wants to learn a trick or two from the pro.”


Four Seasons Tenure

  • Original Ocean Club since 1967, with Four Seasons since 2017
  • First Four Seasons Assignment: Current


  • Nassau, Bahamas

Languages Spoken

  • English

“I arrange matches and offer clinics and private lessons, but the private lessons are the most in demand.” That’s Leo Rolle on the on-court duties of his long-running role as Tennis Pro/Director at The Ocean Club, A Four Seasons Resort in the Bahamas. Why such demand for one-on-one instruction? “Everybody wants to learn a trick or two from the pro.”

Everybody sure does, and with good reason. A fixture since the luxury beachfront Resort became a playground for celebrities and discerning travellers back in the 1960s, Rolle is renowned among new and returning guests alike not just for his talent with a racquet, but for his positivity, availability, and smooth conversational skills on the court. He is always up for a game, he says, and there is always a taker.

“It’s different than it was 30 or 40 years ago; guests don’t seem to want to be set up to play with each other anymore. Now they want to play the professional so they can be sure they’re going to get exactly what they’re after.”

Whatever that turns out to be, Rolle can help them along. His strength as a pro, he says, is being able to pinpoint precisely what needs to be corrected to improve one’s game. Say a guest is squeezing their racquet too tight: Rolle will tell them to hold the racquet with their pinkie finger off. “They’ll say, ‘But I can’t hit it like that!’ And I’ll say, ‘Yes, you can. The way you’re holding it is like driving a car with one foot on the brake. Do what I ask: I’m trying to get you to feel more comfortable.’”  

There are a lot of inspiring stories behind Four Seasons talent, and Rolle’s is right at the top. One of 10 children – “five boys and five girls” – born into a struggling family in Nassau, Rolle’s parents moved frequently from one low-income neighbourhood to the next in the Bahamian capital. One day when he was nine, he went for a walk and by chance looked through the fence of a tennis club to see people hitting balls.

All of a sudden, a ball came flying over the fence. “I ran and got it, and the guy on the other side told me to come around to the gate,” he remembers. “He gave me a sixpence and told me to come back around again tomorrow.”

That night, Rolle couldn’t sleep. “I wanted more sixpence!” The next day, the man put him to work as a ball boy – “He told me, ‘I’ll tell you when to pick up the ball’” – and Rolle never looked back.

He never took a tennis lesson either. Instead, Rolle emulated the various forms of club members whose errant balls he chased at the courts. He put the money he earned in a “kitty” for his family and began playing tennis on his own. He never missed a swing, he says, and he always played at “an extremely high speed.” Those talents took him far, including winning junior titles in The Bahamas; climbing to the #1 ranking in the Caribbean; and, in 1974, qualifying to represent his home country in the Davis Cup.

All of the above aside, Rolle didn’t have the funding to make a go of the tournament circuit. So instead he took his talents to the resort circuit, joining the original Ocean Club in 1967 when it was the only property on Paradise Island and teaching its founder, the late American businessman Huntington Hartford II, to become an ace at the game.  

“Everybody who has come through the Ocean Club over the years, I’ve played with,” he says, fondly remembering but of course providing no details on the Shah of Iran, Bill Gates, Robert De Niro, Sidney Poitier, Richard Nixon, Joan Collins, and many more.

Beyond providing on-court instruction, Rolle oversees the Resort tennis operation – with six Har-Tru courts, including three lit for night play – which falls under the same umbrella as the Fitness Centre. During high season, he occasionally calls in other local professionals to provide lessons at The Ocean Club. “Guests get a choice, either way.”

As for working under the Four Seasons flag for the first time in 50-plus years at The Ocean Club, it was love-love from the start. “So far, so good,” Rolle says. “They respect what I do, and I respect them.”