Maximum US possessions in the Caribbean

I still like the idea of the Bahamas joining the Revolution as its obscure but the population were just sympathetic enough that if they somehow got kept by the Americans in '76 and '78 they would probably stick around.

For that I think you'd need a pretty decisive defeat of the Royal Navy in the Caribbean. That causes a whole different set of butterflies on its own though.

I suppose there's always a chance for a war of opportunity. 1870, during the French Collapse in the Franco Prussian war, the US swoops in and grabs France's Caribbean colonies. Afterwards, it simply writes a cheque to the beleaguered new Republic.

That would be an interesting one.
 
Well naturally maximum expansion would be all of the Caribbean islands. This is a big stretch but not completely ASB. It would require the USA to purchase territory/go to war with Spain, UK, France, Denmark, and the Netherlands at some point. Moreover, the USA would need to feel that Manifest Destiny somehow included the Caribbean. Not sure how that would happen.

In my TL the USA manages to pick up Cuba, Santo Domingo (OTL's Dominican Republic), Puerto Rico, Guadeloupe, and Martinique.
 
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