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Fun:Puerto Rico

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Looking disturbingly similar to the flag of Communist Cuba.
This is an island surrounded by water. Big water. Ocean water.
Donald Trump

Puerto Rico is an unincorporated United States territory that was won from Spain in after a splendid little conflict known as the Spanish-American War. And Spain had previously taken Puerto Rico from the natives. In spite of having over twice the population of Hawaii, which joined the Union at around the same time, it's still not yet a state. Reasons for why this is the case range from "it's too poor and they'll have to pay income taxes" to, strangely enough, "they aren't Americans",[1] while in reality, it's a blend of the English-only movement and Puerto Rico's strong support for the Democrats, possibly with some racism sprinkled in. The region and country are divided between statehood, independence, or status quo.