Denny Derrick: How ÀNI Anguilla's Tennis Pro Is Changing Lives through sport on the Island

Since announcing our partnership with ÀNI Private Resorts at the start of 2025, we’ve had the privilege of spending time with their teams across several of their properties. One thing we’ve found ourselves coming back to again and again is the people: The artists nurturing young talent in Sri Lanka. The educators opening doors in the Dominican Republic. The team members whose lives and passions are deeply connected to the communities around them.

With Wimbledon season upon us, it felt like the right moment to introduce you to Denny Derrick, ÀNI Anguilla's resident tennis pro and former professional player, whose story we recently had the chance to hear firsthand.

Because beyond the court, Denny has spent years helping young people across Anguilla access opportunities through sport, mentoring the next generation of players and supporting local children to pursue dreams that once felt out of reach for him too.

His story is a reminder that meaningful impact does not always begin with a programme, a strategy or a funding commitment. Sometimes it begins with one person recognising potential in another.

Many of us spend a great deal of time thinking about how travel can contribute positively to the places we work in. Denny’s story is a reminder that some of the most meaningful change happens, over many years, through relationships, trust and people who care deeply about their communities.

And sometimes the most important thing a business can do is create the space for that to continue, and flourish.

The Boy at the Fence

When Denny was eight years old, he used to stand outside the fence at a tennis summer camp in Anguilla and watch. His family had only recently arrived on the island, having moved from the Dominican Republic where Denny was born. There was no money for fees. So he watched.

The coach running the camp was Mitchell Lake. One afternoon, Mitch walked over and asked Denny if he wanted to try. Within a week, Denny had a racket, a pair of shoes, and a place at the camp — all of it free.

That moment set in motion a story that has now repeated itself, in different forms, for around 60 young people on the island.

Following the Dream

Denny went on to become one of the most promising junior tennis players in the Caribbean. By 11 he was winning regional tournaments, including the Diamonds International in St. Martin, and earning a reputation that surprised people who hadn't seen him coming.

But his path wasn't straightforward. His father, a man who believed deeply in stability and hard work, wanted Denny to become an electrician. There were two years when Denny stepped away from the sport entirely, working in a shop, quietly unhappy. Then his father made him a deal: win one tournament, and you can pursue your tennis dream.

Denny won. He came home with a trophy and his father told him to follow that dream.

He trained seriously after that, sometimes eight hours a day on the court. Mitch's vision, though, was always bigger than developing one player. He wanted to build the Anguilla Tennis Academy, a proper facility for the island's young people. He and Denny helped raise the money through a ‘Buy a Brick’ campaign, teaching tennis at villas across the island and inviting guests to sponsor a brick to build the academy. Standing at the groundbreaking ceremony, Denny realised that what had once been a dream was finally becoming a reality.

Paying It Forward

Denny went on to train at a high performance facility in Dallas, earned his coaching certification, and came back to Anguilla to give the same standard of training to the kids coming through the programme. He was appointed Director of the ATA's High Performance programme, a role that put him at the centre of everything the academy was building.

The coach at Cumberland University was negotiating a partial tennis scholarship for Denny, but even with that support, his parents couldn’t bridge the financial gap. He stayed in Anguilla and kept coaching instead. That experience became the lens through which he works with every child who comes through the academy now, thinking carefully about what each player still needs to earn a full ride, not a partial offer, because he knows exactly what it costs.

Around 10 young Anguillans have since gone on to universities in the United States on tennis scholarships. Denny says it's one of the things that brings him the most pride — watching those kids grow up, go to college, and come back. And they do come back. Some return during the holiday season, picking up short coaching stints or giving motivational talks to the younger players coming through. As Denny puts it, they come back and tell the story to the younger generation, and the story just keeps growing.

Last year, the academy held an alumni night. Around 50 former students turned up and played together on one court, Mitch coaching and everyone catching up. The kids who once stood where Denny stood are now business people, professionals and coaches in their own right.

Today there are around 60 kids at the Anguilla Tennis Academy, aged 5 to 17. At any given time, 8 to 10 are on full sponsorships, their fees covered by the academy or by guests who visit, see potential and decide they want to be part of their future.

The goal for this year is to resurface the courts and stage the Anguilla Cup again. The Cup is an established annual event on the ITF calendar, held each November at the academy, and has previously drawn around 200 players from across the world. They are hoping to bring it back this coming November.

What ÀNI Makes Possible

Denny's path to ÀNI came through a guest he had been teaching around the island. Ira Bloom, who was then CEO of ÀNI Villas International — as ÀNI Private Resorts was previously known — had originally come to Denny wanting lessons for his father. Before long, he was learning himself, got seriously into it and started competing. One day he asked Denny if he'd consider becoming ÀNI's tennis pro.

The arrangement itself is simple: ÀNI employs him as their resident tennis pro, and when there are no guests to teach (and anyone who works in hospitality will know those quieter seasons), he spends his afternoons at the academy. Some guests visit the academy while staying at ÀNI and end up sponsoring a child for a year.

Later this year, ÀNI will open its second Anguilla property on Shoal Bay East, one of the Caribbean's most celebrated beaches: ÀNI Shoal Bay. The new resort will include a tennis court perched at the top of the property with views across the sea, alongside a pickleball court — and with it, a new chapter for Denny's work on the island: more guests, more visibility for the academy, and more opportunities for the next generation of players coming through.