- July 22, 2026
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Trevor Sinclair’s first coaching endeavor wasn’t with any professional team or youth academy. It wasn’t a private lesson with a gifted athlete looking to elevate his game.
Sinclair, who at 17 already had begun his professional soccer career with Blackpool in England, was coaching two boys who were no older than 6.
As a coach, he stuck to the basics and kept it fun. He found enjoyment in stepping away from the sport’s more advanced aspects.
“From there, I always knew I had that nurturing way about me, to help people,” Sinclair said.
It was a humble entry into the profession, but it was a first step in a coaching career that eventually led him to becoming the lead assistant of the Lakewood Ranch-based Sarasota Paradise. Sinclair was chosen for the role by coach Mika Elovaara ahead of the club’s first professional season in USL League One.
Now 53 years old, the Dulwich, England native fully embraced coaching after his playing career (1989-2008) ended. A winger and midfielder as a pro, Sinclair competed in the Premier League for the Queens Park, West Ham, and Manchester City.
One of the highlights of his career was representing England at the 2002 FIFA Men’s World Cup, helping the team to the quarterfinals, where it fell, 2-1, to eventual champion Brazil.
“As soon as someone like Trevor walks in the door, that’s inspiring,” said Paradise defender Declan Watters. “He's someone who’s been there and done that at the absolute highest level. That’s not something you take for granted.”
The Englishman never forgot his first coaching experience as a youngster, but even so, it wasn’t an avenue he was eager to explore after playing his final match with Cardiff City in 2008 in the EFL Championship.
Jumping into coaching was about the last thing he wanted to do.
Living in Dubai at the time, he anticipated stepping away from the field and soaking up the sun, but relaxing wasn’t so easy with four sons who had burgeoning soccer interests of their own.
Reiss, Isaac, Sky and Kobe Sinclair started taking lessons from local coaches. Their father wasn’t pleased with what they were being taught — or rather, what they weren’t.
“Honesty, integrity, being fit, being fair… I wasn’t seeing that displayed,” said Trevor Sinclair. “So I decided to step in and start coaching my own sons. Then, before you knew it, I was coaching and my sons weren’t even there.”
He began dedicating his time to developing young academy players for the professional game, before he accepted a job in 2024 as an assistant coach for the Jamaica Men’s National Team.
His coaching exploits took him to Jamaica before Lakewood Ranch. In August 2024, he was named as an assistant for the Jamaican men’s national team in the lead-up to this year’s World Cup.
Jamaica failed to qualify, though, for the World Cup.
Elovaara called Sinclair late last year while building the coaching staff for the Paradise, who were getting ready to play their first professional season.
Elovaara, who has known Sinclair for 14 years, wanted him on the sidelines. So he asked Sinclair an important question.
“I asked Trevor about why he hadn’t gone to a Premier League job as an assistant coach — which surely would have been available for him,” Elovaara said. “He told me that he (wanted) to learn to become a coach.”
Elovaara said plenty of soccer pros, take on jobs immediately after retirement from playing and they're rarely ready for that task.
Sinclair wanted to work his way up like he did during his playing days.
Upon graduation from the then-Bobby Robson School of Excellence at Lilleshall in 1989, his teammates went to Premier League stalwarts like Arsenal, Manchester United and Tottenham Hotspur, but not Sinclair.
The aspiring soccer star chose to join Blackpool, which competed several divisions lower. He promptly became the club’s youngest-ever player at 16 years and 5 months old in August of that year. His record stood for over 17 years.
“I wanted to make the decision myself, and I made that decision — similarly to my coaching,” Sinclair said. “I wanted to start at the bottom, start coaching kids (and) start learning about humility and empathy for kids.”
His current stint with the Paradise began in January. Visa issues, though, complicated his arrival to the U.S. and he was unable to join the team in-person until late April.
Matches and practices were only available to him through videos during that period. He stayed in touch with coaches and players over the phone, but had no face-to-face interactions.
He tried to establish and strengthen relationships remotely. There was only so much he could do before the season began March 7, and before he made his in-person debut April 22.
“It’s not the same,” Sinclair said. “I had to miss out on two, three, four weeks of what I would usually do and get straight on it. It was a little bit out of my comfort zone.”
May, June and July have allowed him to get comfortable.
More than three decades have come and gone since Sinclair coached a pair of young boys — neither of whom thought about the pros, but both of whom wanted to have fun.
These days, he offers his tutelage to 27 pros in Lakewood Ranch, all of whom hope to reach even higher levels of the sport. It’s an opportunity he was quick to accept.
“I had no hesitation,” Sinclair said.
