@Jack V Savage @HomerThompson @Rod1 This actually popped into my mind at work yesterday. Trump's "relations with Russia have never been worse" got me thinking of the Cuban Missile Crisis and how he would have handled it.
But then, after awaking from the blackout I suffered from existential panic, my mind shifted to how he would deal with Fidel Castro. I mean,
clearly the guy has a strong affinity for autocrats and can be swooned by the sexiness of authoritarian power. But guys like Jong Un, Jingping, and Putin -- all whose stocks/countries have benefited bigly from Trump's being a dumb fuck -- aren't exactly that iconic. Castro, on the other hand, had legendary charm and charisma. He was so iconic that he was beloved as a celebrity in the United States even after he got in bed with the Soviets.
In short, I think that, given Trump's weaknesses and Castro's strengths, the Cuban Missile Crisis would have ended with Trump giving away Florida & Puerto Rico to Cuba and then dropping a bomb on Washington DC out of sheer contrition.