From MoBay to Kingston: Lessons in Grit and Growth
The Red, White & Black Diaries is a behind-the-scenes journey into the heart of Trinidad and Tobago football — told from inside the camp, on the road, and through the voices of those living it.
It’s not just about the matches, but the moments in between — the long bus rides, the laughter in hotel lobbies, the quiet focus before kickoff, and the pride that comes with wearing the national colours.
From MoBay to Kingston: Lessons in Grit and Growth
Inside Yorke’s first Caribbean tour — a trip of bonding, belief, and building the Red, White and Black spirit.
Jamaica, February 2024
Our last trip to Jamaica (prior to the September World Cup qualifier) came in February — two friendlies against the Reggae Boyz, first at the Montego Bay Sports Complex and then at the Anthony Spaulding Complex in Kingston.
The matches were staged as part of the Memorandum of Understanding between the Jamaica Football Federation (JFF) and the Trinidad and Tobago Football Association (TTFA). President Kieron Edwards had announced the series and extended thanks to the JFF for hosting our team after we had welcomed them to Trinidad the previous year.
It was the heart of Trinidad Carnival season — the atmosphere back home buzzing — while Dwight Yorke was stepping into his first Caribbean assignment since being appointed head coach three months earlier. The squad was made up mostly of home-based players, with a few North America-based and Jamaica-based pros joining in.
We arrived at Norman Manley International Airport in Kingston before a one-and-a-half-hour bus ride to Montego Bay. Discussions between the TTFA and Yorke had focused on ensuring the players were properly accommodated, and the decision was made to base the team at the RIU Resort in Montego Bay. It was luxurious, lively, and packed with tourists, especially from the UK. Yorke was instantly recognized everywhere he went — photos, handshakes, the usual warm Caribbean welcome.
TTFA President Edwards traveled with the team — gaining valuable insight into the inner workings of an international trip with Yorke at the helm. Russell Latapy’s name still echoed among the older Jamaican fans who remembered his teenage days playing there. Along with Yorke, names like Jerren Nixon and Arnold Dwarika sparked nods of nostalgia. For Kevin Molino, there was personal history too — he had scored the winner when T&T’s U-17s beat Jamaica 1-0 in Kingston to qualify for the 2007 FIFA U-17 World Cup.
Yorke held an early meeting with players and staff, with Edwards in attendance. It was straight talk — clear expectations about the mission ahead, upcoming Gold Cup qualifiers, and the World Cup campaign. Terms, conditions, match fees, everything was addressed early. The message was simple: we have business ahead, and we need to be serious and focused.
The first training session took place at Montego Bay United’s home ground. The surface wasn’t great uneven and patchy and Yorke made his feelings known. The session was short, sharp, just enough to get legs going while avoiding injuries.
Behind the scenes, Team Manager Richard Piper, Yorke, and President Edwards stayed in close contact with the JFF. Arrangements were soon made for the team to train at the Mount Pleasant Football Academy in St. Ann. The difference was night and day, a pristine, modern facility tucked away in the hills. It was the home of Jamaica legend Theodore Whitmore, who greeted the team personally. Club owner Peter Gould, an Englishman, also showed up to meet Yorke and the staff.
Mount Pleasant was a clear statement of intent — professional, well-kept, and forward-thinking. From the restaurant and gym to the dorms and classrooms for young players, it was obvious Gould had invested wisely and with purpose. It reflected a vision for development — something Yorke himself often spoke about when talking about Trinidad and Tobago’s own football journey.
Yorke made sure that even off the pitch, the camp felt united. Staff bonding was part of the daily rhythm, with Latapy always playing his part, cracking jokes, sharing experiences, keeping spirits high. The players were always part of the conversations too, bridging generations and building chemistry. We even celebrated a birthday on the trip — cake, laughter, and a few heartfelt words. Yorke and the staff shared stories from their playing days, past camps, and moments that shaped them. Being on a trip like this at national team level is like doing a master’s degree in football life,lessons no university can teach, only experience can. Being around high-caliber professionals, watching how they move and handle moments, is an education in itself.
In between training sessions and matchdays, Sportsmax TV landed the first exclusive one-on-one interview with Yorke at the RIU. The conversation went beyond Trinidad and Tobago — touching on his Manchester United legacy, leadership philosophy, and long-term vision as T&T coach. Even while on tour, Yorke was constantly fielding calls and inquiries from foreign media — particularly from the UK, where his name still carries weight. The Jamaica press also turned up for their mandatory 15 minutes of training coverage, eager to get a closer look at Yorke and his team in action.
After a couple days of prep, it was finally matchday at the Montego Bay Sports Complex. T&T had previously beaten Jamaica 1-0 in a friendly there in 2023, but memories still lingered of losing the Caribbean Cup Final on penalties in 2015 to the same opponents.
Games between the two nations are always scenes — hyped, fierce, and full of rivalry, no matter the stakes. Whether competition or friendly, there’s always something in the air. As we walked into the venue, stepping off the bus, you could feel it – the Jamaican culture, the breeze, the rhythm in the stands.
Yorke, alongside his assistant Neil Wood, a former Manchester United man, walked straight out to the pitch after dropping off their belongings in the team’s dressing room, a tight space. Moments later, Yorke and his former assistant coach at Manchester United, Steve McClaren, embraced warmly. What followed was a lively conversation, part banter, part business as they exchanged thoughts about football, their current jobs, and what lay ahead.
Then it was down to the match. Both teams gave a good account of themselves, with the home side edging a 1-0 win. It was a solid, measured test for the T&T team, giving Yorke a chance to see several players in action against a strong Jamaica squad, made up mostly of home-based players. Among the T&T group were promising college players Derryl Garcia and Lindell Sween.
Captain Kevin Molino reflected after the game:
“The result doesn’t reflect the game. I think we had a good showing in both halves especially the first half. We kept the ball and worked to the plan that Yorke wants for us to get familiar with.
We get another opportunity again to play on Sunday to showcase our talent and show what we can do. It’s crunch time now. This is the only game before our upcoming one in March, and we’re just looking for a turn.”
We knew things would get intense in the days ahead — no coach wants to lose two on the trot, and bragging rights always matter. The players understood the need to step up, but Yorke stayed calm. He kept the mood steady a mix of encouragement, light banter, and quiet determination. Everyone was still getting to know each other better, including the staff, with some members joining the setup for the first time.
All the while, life went on around the team — hotel guests in and out, music echoing across the beach, the Caribbean breeze rolling through the open-air resort. The RIU was windy, full of evening shows and energy, but the team stayed locked into its rhythm: video sessions, technical meetings, rehab and recovery, meal times, and strict adherence to the schedule. The discipline was clear with the tone of a team trying to build something bigger than just two friendly matches.
Then came the move to Kingston — down to the heart of Jamaican football culture for the second friendly at the Anthony Spaulding Complex in Arnett Gardens. The drive itself was a window into real Jamaica — the streets, the walls, the faces, the rhythm. You felt the soul of the place long before stepping onto the pitch.
The venue wasn’t glamorous with fans just feet away from the locker room, bleachers practically on top of the field but it was rich with history and tradition. You could sense the pride, the energy, the football heartbeat of Kingston.
This time, Trinidad and Tobago looked sharper. The team took a 1-0 lead through defender Josiah Trimmingham, a well-taken goal that brought a roar from the bench. But football can be cruel — Trimmingham would also be involved in the late equalizer for Jamaica. As the final whistle blew at 1-1, Yorke smiled faintly, acknowledging it had been a good test, but the players felt it as they knew the win was within reach.
After the second game, the post-match press conference took place in a small, almost empty room — basic setup, just a few tables and mics — but it didn’t dampen the energy of the Jamaican journalists. They were eager, waiting for Yorke, questions ready. One asked if he thought his team had been unlucky not to win. Yorke gave his usual composed response, focused but firm, before the Jamaica press officer signaled to wrap it up, reminding everyone that McClaren still had to address the media next.
Yorke’s message afterward to his players was clear and measured:
“We showed that we can play. That we can come to these places and get results. But we have to work harder, believe more, do more, take care of ourselves. Don’t just go away from here and feel things will get better on their own. We can’t just show up and expect results.”
At that time, no one knew that Trinidad and Tobago would have to return to Kingston months later for a crucial World Cup qualifier — and then host Jamaica in a decisive home fixture in November. But looking back, the groundwork was being laid. The culture, the understanding, the togetherness, it was all being built on that February trip.
Now, as the story continues, you can feel it — the result, the moment, the reward, it’s due for Trinidad and Tobago.
