This is probably the most realistic way for Jamaica to be a Caribbean leader. If Trinidad and Tobago had been less able to demand independence at the time (If a major hurricane had hit them soon after the founding of the WIF, for instance), the West Indies Federation would likely have stayed together with Jamaica as its only plausible center.
Problem: Trinidad lies outside of the hurricane belt, so it would be a very rare event, not to mention borderline ASB, to have a hurricane hit T&T.