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I always thought the decision to trade Cuba for Florida at the end of the 7YW was an awful decision. Obviously, Havana was a much more important port than anything in Florida, and would bring in tons of revenue. Leaving Florida for the Spanish would keep a foreign threat on the southern colonies, so they would need more British protection than OTL. And appeasement doesn't work against a coalition that "knows" it's better than you.

But I'm having a hard time imagining how Britain would keep control of Cuba. First, Spain would be hell-bent on getting it back. They'd start coordinating with France for a war of revenge, and Havana would be the #1 target. Second, the British would control an island populated by sworn enemies. "Guerrilla" might enter the English language a few decades earlier if the British have to pacify the island.

So I think you'd want to:

  • Encourage as much trade as possible with the colonies and England in order to integrate the economy with the empire. Now Cuba (and the colonies) might hesitate to rebel if that trade will be disrupted.
  • Put forth something like the Quebec Act. Keep Spanish law, Catholicism, no oaths of allegiance referencing the Protestant faith.
Any other ideas? The loss of income to Spain would make it less effective in the next war, but I don't think that would stop them if they have French support.
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