Called the ‘next Ryan Giggs’, he starred for Manchester United’s youth side and trained with first team stars Cristiano Ronaldo and Wayne Rooney.
However, in 2006 a horror ankle injury forced the Cardiff-born starlet into early retirement.
Then in 2013, he launched his own business – selling high-end watches for over £250,000.
Today, Calliste lives a dream life in Dubai while managing his stunning jewellery and designer accessories shop in the heart of London’s exclusive Mayfair.
If you are looking for a classic Rolex Daytona for £30,000, or even a collector’s Hermes handbag priced at around £20,000 – his Global Boutique on South Molton Street is the go-to place for that kind of luxury.
It has allowed Ramon and his family to enjoy a more sustained lifestyle he would have enjoyed if he continued in football.
Speaking to SunSport from his home in Dubai, Calliste revealed: “Watches were always a passion for me.
“I learned the trade quite quickly, got obsessed with Rolex references, and the business has thankfully grown since then.
“We recently launched a very high-end luxury store in Mayfair, and I’m happy to say it’s doing very well.
“We sell watches, beautiful jewellery, and we have a certain amount of accessories, including Hermes bags, which is something we will expand on because they are selling very well.
“Having a Mayfair premises, with the amount of clients that walk-in from around the world and the type of clients we attract, has been amazing for business.”
Previously, Calliste told SunSport he sells watches from around £50,000-£70,000.
And he often gets a £150,000-£250,000 sale in a market where clients can make money from pieces that become collector’s items over time.
Ramon’s company is making roughly £5million-per-year, more than he might’ve had made as a professional footballer.
“It’s always a Rolex driven business, so those are the most popular.
“But there’s always the big ticket items, the Patek Philippes, the Audemars Piguets and Richard Milles that sell for mega money.”
Calliste looks back at his football career with fondness. In 2000, he signed a contract with Manchester United alongside Sir Alex Ferguson.
Recalling that moment, he told us: “When I got to Old Trafford I met Sir Alex Ferguson, which was an incredible experience.
“Seeing everything for the first time, I went into the famous room where everyone meets him.
“It was a special, I wasn’t fazed by much when I was young, but he had the aura of a great man.”
Ramon didn’t play for the United first team, but he got his chance to train with some of their superstars.
“We didn’t always train with the first team, but sometimes we’d have five-a-side games.
“I aspired to train with them permanently, and it was amazing when I did get the opportunity.
“I trained with Rooney and Ronaldo, which was a big deal.”
Injury wrecked his career
After Ramon was released from Old Trafford, he starred for Liverpool’s reserves.
He was their leading goalscorer in the 2005-2006 season, but left for Scunthorpe for first team opportunities, after then-Wales manager John Toshack told him he needed to play more.
“It wasn’t initially what I wanted to do, but Toshack told me I needed to play competitive football if I wanted to break into the Wales first team,” he said.
“I thought, let’s do this and took a contract. Preseason I got a bad ankle injury straight away and I never really recovered from it.”
In 2009, Ramon had decided he’d had enough of football.
He had spells at Cambridge City and West London Saracens in the Middlesex County Football League, but was plagued by the dislocated ankle injury that robbed him of his dream.
Living the dream
But everything happens for a reason. Now, Calliste is happy in the Middle East. His children are thriving in a new environment, and destiny gave him a different calling.
“I feel lucky I am in a fortune position to help myself and my family,” he said.
“Dubai is a very beautiful and safe place, as well as a huge market hub. There are opportunities here and there’s lots of money here too.
“It was an all-round decision for my family and for my children who have excelled at school here.
“In comparison to where I started when I was younger, my life has changed incredibly.
“I have now built something that lasts forever. When you play football you have a certain shelf life.
“Now I look at having the injury as a blessing. I’m very grateful for my change of direction, although it was tough one to accept at the time.
“However, I’m thankful that this path has been very good to me… long may it continue.”