Is he not going to train with Jabloteh first? I do not think he is sure to make the team.
Yes, I think this is getting blown out of proportion. First he has to make the team at Jabloteh. Then he has to do well enough to catch Latas' eye (though I suppose if Tinto did why not him). Then he still has to be selected in the final 23. On top of this T&T still have a difficult road to qualify.
There is a guy named Pat Sappleton who played at a similar level in England as Gullick who left England to play in the DPL in Jamaica with hopes of playing for the national team. I think he played about 38 minutes for Village United (I'm not sure if he got hurt or didn't play well but in that game his team lost 4-0 and I think he was at fault for one of the two goals he was on the pitch for). Anyway hes now back in England playing (and starting) for Maidenhead United who are a league above Gullick's team. The point being perhaps some of the players of in England think that the national teams are worse than they actually are. To be fair to them many players for teams like Montserrat and Anguilla do come from these divisions.
