The British Isles became the United Kingdom. What might the Caribbean islands have been?

Yesterday it occurred to me: what if Puerto Rico and Cuba had federated long ago?

This morning, while measuring the nautical distance between their nearest port cities, I got hit right between the eyes by the island of Hispaniola, home to the Dominican Republic and Haiti. Immediately thereafter I noticed Jamaica, Bahamas, Turks and Caico as well as the rest of the Caribbean islands.

Perhaps they would all have federated had they been colonized by the same power or, more likely, had they been colonized by the same power in the age of motorboats rather than sailboats, of telegraphs rather than letters, of movable type rather than manuscripts, etc.

History is all manner of coincidences at war with one another, as noted by humanity’s most ancient texts. Political maps are tragicomedies.