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Today North Korea is an isolationist “hermit kingdom” that regularly engages in saber rattling with its southern neighbor and USA, is the only industrial nation to have suffered suffer large-scale famines and widely believed by westerners to be one of the worst places on the planet. By contrast, Cuba is not viewed nearly as negatively by the world and in fact is praised in some areas (e.g.: its healthcare and humanitarian medical assistance in Africa and elsewhere).

The challenge here is to reverse the situation (isolationist “hermit kingdom” Cuba that has few international friends and engages in constant saber rattling, widely believed to be one of the worst places to live on Earth vs a North Korea that while still a dictatorship has a much better international image and whose regime is often admired in leftist circles for its achievements abroad and domestically). POD has to be after North Korea becomes communist (NOTE: Cuba also has to go communist at some point too).

I am thinking that maybe a different outcome of the Cuban Missile Crisis can result in this. Say that US leadership discovers the missiles in Cuba later or under a different president and decides that trying to take them out would be too risky. Somehow the possession of the nukes passes from the Soviets to the Cubans. As a result, Cuba has several atomic bombs it can theoretically lob at Florida and can “hold Miami hostage” just like North Korea is believed to hold Soul hostage with the artillery at the DMZ.
Maybe a surviving USSR can prop-up this ATL Cuban regime for its own reasons like how China is believed to prop up the OTL North Korean regime? (though a lot of the problems faced by both Cuba and North Korea can be attributed to stop of Soviet aid in 1990s, so if the USSR does not collapse the ATL Cuba might not become as "crazy" as OTL North Korea).
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