Trinidad and Tobago: From a World Cup to complete obscurity

Thomas Sadler
6 min readMay 5, 2022

The 2006 World Cup was the first one I can remember, watching the final in an Italian restaurant imaginatively named The Mona Lisa, surrounded by impassioned waiters waiving various hand gestures around, particularly towards Zidane throughout the match. I can’t help but feel nostalgic about that tournament and with those rose-tinted spectacles adorned I tend to think any country involved in that World Cup is slightly better than they actually are.

I think everyone around my age were gathered in assembly to watch that England match against Trinidad and Tobago, or perhaps I went to slightly lax school… Regardless, when Peter Crouch clambered over Brent Sancho to nod England ahead, I remember the shrill cheers around me, and weeks later we’d all be imitating the robot dance with varying degrees of accuracy.

Whilst that tournament ended in familiar fashion for England, losing on penalties to Portugal it remains Trinidad and Tobago’s sole appearance on the world stage.

The Caribbean islands had flirted with the world cup in 2002, failing at the final hurdle in the qualifiers, but they had amassed a squad of players, primarily playing in the UK, that would eventually lead them to relative success.

Looking at the 2006 World Cup squad, there were a significant number (15) of the 23-man squad that were playing club football in the English or Scottish leagues. Stand out players included West Ham keeper Shaka Hislop, young target man Kenwynne Jones and Manchester United icon Dwight Yorke who was playing in Australia at the time, before joining Roy Keane’s Sunderland.

Post-Colonial Isolation

Whilst other Caribbean nations like Jamaica have a vast diaspora they can call upon, with the likes of Michail Antonio springing up out of a population of around 800,000 people in the UK, Trinidad and Tobago have no vast reserves they can look towards with only around 25,000 people in the UK having ties to the islands. However, this isn’t a new problem and it also effected the 2006 squad with only 3 players (Hislop, Birchall and Cox) not born in their homeland. Whilst a significant proportion of the squad played their football abroad, the vast majority of players had developed (under 18 years old) in Trinidad and Tobago before moving overseas.

The aforementioned Dwight Yorke is perhaps the poster child of youth development on the islands. In 1989, Aston Villa manager Graham Taylor scouted an 18-year-old Yorke whilst on a pre-season tour of the West Indies, a year later and Yorke would make his debut for Villa before signing for Manchester United in 1998, scoring 48 league goals in 96 games and winning a treble along with a few other trophies under Ferguson.

1989, Dwight Yorke (right) alongside soon to be manager Graham Taylor and former teammate Colvin Hutchinson

Many of the generation shared similar stories about their early careers, playing youth football in their homeland before being scouted by English or even Scottish clubs. At the time work permits or visas weren’t an issue for many of the islanders, following the country’s independence in 1962 the subsequent generation were afforded a British passport should they apply. As a general rule of thumb many post-colonial residents could apply for British nationality so long as their father was born in a former colony and didn’t already hold another nationality.

A generation on from the world cup and Trinbagonians are no longer automatically eligible for a British passport, which has led to a series of events that have all but destroyed the national team. Without any hope of gaining a work permit due to the league’s respective level, and no hope of a passport there is no longer any reason for teams based in the UK to scout the West Indies in the hopes of unearthing a new Dwight Yorke.

That generation was the last to be eligible to play outside of Trinidad and Tobago without significant obstacles in the way of work permits, green cards and visas. Moreover, any decent players are increasingly likely to move into the America league system rather than make the journey across the pond to the UK.

The Current Squad

Amongst the most recent call-ups to the national side not a single man plays in the UK, whilst 5 still play in their homeland many more (8) play in America. Even those that have made it to America don’t play in the MLS, instead they’re based in step two of the pyramid in the USL, where the quality of football is roughly equivalent to the National League in England.

Whilst recent call-ups do include Joevin Jones a left back for Inter Miami, and Kevin Molino from Colombus Crew they are both on the wrong side of 30 and there remains an undeniable lack of quality in comparison to that 2006 squad.

There is perhaps a glimmer of hope in young winger Levi García who left for AZ Alkmaar aged 18 and now plays for AEK Athens in the Greek Super League. He’s racked up 4 goals and 3 assists in 26 games this season helping AEK to 3rd in the league, still some ~20 points away from 1st placed Olympiacos. He’s your archetypal winger, good on either foot, likes knock the ball past his opponent but he’s also excellent in the air.

The Future of Trinbagonian Football

In theory there’s still the same untapped potential locked away in Trinidad and Tobago as there was in the 1990s, as shown by Levi García’s success, but there’s no longer any easy route for that potential to be nurtured to a World Cup standard. Dwight Yorke was a one off and there will most likely never be another player of equal quality to come from the islands without a significant change.

Whilst other nations of small stature have famously improved their national side through investing in youth football, the likes of Iceland and the Faroe Islands have done so under the promise of free movement throughout Europe. Players produced under those youth systems eventually left for more competitive European leagues, which is fine because the focus was on improving the national side rather than the Icelandic football league. In stark contrast, without the ability to move abroad to more competitive leagues any talent that youth systems in Trinidad and Tobago may produce will be more likely to stagnate than grow into another World Cup squad.

America is seemingly becoming the destination for so many expat players, so the future of Trinbagonian football would appear to rest upon the shoulders of other countries. Without the competitive nature of European football they’re forced to rely upon less developed footballing countries that are struggling to nurture their own national teams. If footballers remain isolated in Trinidad and Tobago, it’s difficult to see how they will ever be able to emulate their past success and qualify for another World Cup.

Thanks for reading this piece.

I can be found on Twitter and Instagram @MightyFTN where I tend to post more illustrations and thoughts about football.

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