Lots of valid points raised in this thread, but to me, there have only been 2 periods when clubs ever visited Trinidad on a regular basis (or maybe I'm not old enough to remember):
1. Around 1990, when Strike Squad was flying high and teams like Villa, QPR, Leicester seemd to have a genuine interest in TnT football.
2. Around 1999/2000. Then, the international (i.e. - English) clubs stopped coming just around the time England lost their bid to host the 2006 World Cup (which was in 2000).
Jack decided CONCACAF would be backing England in the first round of voting for the host nation (although it was clear they were never gonna win it), then switched his vote to South Africa once England got knocked out. At the time England were a very unpopular choice because everyone wanted SA to win, and, even worse, England had gone back on their promise to back Germany's bid rather than launch their own. They need all the help they could get, and Jack, and by extention TnT, were a focal point of their bid.
(Incidentally, alot of our players moved to UK clubs around that time, work permits didnt really seem to be much of an issue.
)