best POD for Cuba as US state or possession

What would be the best POD for Cuba to become either an American/Confederate state or an American possession (the latter, along the lines of the Philippines or Puerto Rico)?

- no Teller Amendment (which prohibited the US from taking over Cuba outright)
- no Spanish-American War
- Confederates winning the Civil War
- anything earlier than any of the above ... ?
 
- no Teller Amendment (which prohibited the US from taking over Cuba outright)

This is probably the simplest, easiest to accomplish, and would result in Cuba entering the US the quickest and being in the US the longest.

Cuba is more likely to be on their own after a (later) successful revolt with no Spanish-American War, and a surviving Confederacy would need several decades to get the strength to either take or buy Cuba from Spain, and then you have to deal with a second war to reunify the country, and that’s just messy.
 
This is probably the simplest, easiest to accomplish, and would result in Cuba entering the US the quickest and being in the US the longest.

Cuba is more likely to be on their own after a (later) successful revolt with no Spanish-American War, and a surviving Confederacy would need several decades to get the strength to either take or buy Cuba from Spain, and then you have to deal with a second war to reunify the country, and that’s just messy.

Whatever way, I'm sure that might very well butterfly away the 1959 Cuban Revolution, the subsequent communist regime, the US embargo, etc.?
 
Top