redlightning
Banned
What if following the Spanish American War, the United States annexes Cuba and makes it an American territory and eventually is granted statehood during the 20th century?
Difficult for the reasons others have noted. However, one option the US could have considered was only annexing part of it (or, rather, more than it did). They would seize the entire Eastern tenth, quarter, or third, for example, instead of just the Gitmo area.
They might have some insurgency, but it'd be on a much more manageable level. Then, they could make the annexed area a territory. If the neighboring areas of Cuba saw that the US territory portion was better off, they might eventually request annexation, potentially even 'rebelling' against the Cuban government and asking the US for help.
So, you might wind up with a US territory/state that only includes part of Cuba, but might grow over time.