I don’t mean in the cultural sense, I mean in the political sense what’s the most likely place to achieve statehood? This could be a GQ but I thought maybe it’s one that’s debatable.
Wash DC. Even though it’s not very likely at all, it’s still the most likely.
Or perhaps CA would split in 2 and one half would be considered the 51st state.
Next, I’d list Puerto Rico.
I don’t think it would be politically possible to add one new state. Alaska and Hawaii were ratified partially because Alaska was mostly Republican, and Hawaii was mostly Democrat, and they had similar sized populations. Neither party would ratify a state that was likely to give the other more power in Congress. If you could find two candidates for statehood that balanced each other politically, there might be a chance.
Interesting, I hadn’t thought of that aspect. So the likelihood of it ever happening is low?
Yep. Unless one party gains a large and long-lasting majority, and that has never happened due to the self-correcting nature of American politics. Well, perhaps DC and Puerto Rico could be balanced by Alberta and Saskatchewan. 
Texas was admitted with the condition it could split into as many as 5 states, but I believe that’s been repealed.
North Dakota!
They’ve got the Peace Garden, and grain, and, um, grain.
There’s a NORTH Dakota? Next you’ll be telling us there’s a NEW Mexico.
Cuba, after Castro dies.
That’s an interesting idea. Would you expect Free Cuba to lean to the left or to the right?
Given its lack of natural resources, poor infrastructure (though perhaps I shouldn’t mention that), & its frequent bombardment with hurricanes…I’d say it wouldn’t lean, so much as lay flat on its face.
It shouldn’t even be taken seriously.
What, we can’t use 42,803 more square miles of Florida?
I think the cities would lean right and the campesinos would lean left, but what do I know about Cuban politics?
You have it reversed. Outside commentators regarded Hawaii as being a Republican area, and Alaska as a Democratic area, during the time of the statehood debate. That they are the opposite now is due to political developments either just before statehood (Hawaii) or after statehood (Alaska).
To answer the question, Puerto Rico strikes me as being more likely currently than the District of Columbia, largely because the District of Columbia statehood movement seems currently to be more focused on gaining voting rights in the House than outright statehood at the moment.
I stand corrected. Thank you.
Another key factor is the fact that there needs to be a constitutional amendment to allow DC to become a state; Puerto Rico would jsut need to pass a referendum. I would be very surprised if Republicans would be able to muster an argument to keep PR out of statehood if they applied, no matter the political ramifications. It would be a much less dicey proposition to oppose an amendment; that has already failed once without too much stir.
I thought there was a Straight Dope column on this, but I could not find it using the Search function. But has it been repealed? When I was growing up in West Texas, there would be the occasional suggestion that we break away, out off frustration at the real or perceived situation of very little state money making its way out there.
Otherwise, I’d say Puerto Rico offhand. I can’t see Washington DC becoming a state.
Mexico. It would be split into at least two States and we could spend money on building an infrastructure and such instead of a wall and solve much of the immigrants (legal, illegal, current and future) all at the same time.
And then we could all pop down to Hell to get ice cream. Oddly enough, we recently discussed this.
Try thirty-one states.
Wasn’t there a plan in the 19th century to turn Cuba into 4 “slave” states? I could’ve sworn I read that somewhere. Puerto Rico never even entered the mix.
I, for one, would like to see a North California and a Long Island State.