We seem to have beaten this debate to death over the years. those new to the board are only recycling debates.
Any country can be a one off. New Zealand, El Salvador, Honduras, Canada, Jamaica, Cuba, Haiti etc have all been to the dance and I respect them for that. In my view T&T's approach and dear I say Jack's is to get to the dance, in a short cut fashion. Roll the dice maybe is we turn!!!!!!
Countrys that have success and are consistent in football have a FOOTBALL STRUCTURE. Some are far more elaborate than others but they have a structure. For some football is part of their culture, it is in their blood, while others have a different approach ( example USA).
For those that lack a structure they have Academy and / or several players applying their trade in top flight football. Eg. Senegal's Team had 21 of the 22 players playing outside of Senegal in the French 1st Division. Similarly at present Ivory Coast where 16 of its members come from one Academy established years back by a french coach named Guillion (spelling?).
Trinidad was at one time extremely passionate about Football, as a matter of fact extremely passionate about sport in general. Cycling use to sell out, with people travelling from North to South to East and vice versa to watch. It was the same with football and cricket.
Sadly this passion for the local game is dead, man can sit home and watch the best almost every night in leagues World Wide.
Compound that with a total disregard for Sport in schools, communities etc. by the private businesses and government and what you have is present.
Trinidad may one day make it to the WC, this rounds is as good as any. But the truth is we have not invested in the sport in a planned manner that guides us to the best possible potential for success. Sad to say but it the same lack of foresight for long term objectives that have our economy, government, education, medical, social issues on a whole in the state it is in. Modern Football like all the arts require study, application, dedication and discipline, a football education now is thorough. But without a path that at least promises reward for such study and dedication, why do it?
One day, maybe one day Trinidad will indeed have this structure. Maybe getting to a WC is what is required to attain it. Howevber, I doubt that because the it did not happen for the "one off's" More than likely the financial rewards for getting to the WC, will enter pockets who feel they deserve the reward and the game will remain for ever a roll of the dice.