IMO, Michael never really gave up on Cuba. It was all-important: Getting Roth’s Havana casinos, combined with his Nevada holdings, would make him the biggest legit gaming operator in the Western Hemisphere. Letting the Havana casinos slip to other gangs, like the ones Roth promised pieces to, would weaken him.

After the Tahoe shooting, Michael knew he couldn’t do business with Roth—it was either kill or be killed. He came to Havana, and had Fredo deliver the $2 million to him, to string Roth along so he could buy time to find out who was the traitor in his family. He had to leave Havana with his money to avoid being caught up in any investigations of Roth’s murder.

Michael had reason to believe he might be able to do business with the rebels. Castro had not yet declared himself a Marxist/Leninist, and tourism was Cuba’s third-largest source of revenue after mining and agriculture. I’m guessing that his plan was to wait till the dust settled, then make an approach to the new regime, which may already have learned, from his bringing the $2 million to the island, that he was willing to pay in order to play.

As it happened, Castro closed the casinos almost immediately. But, he reopened them after a noisy demonstration by out-of-work hotel and casino employees—and even hired former heavyweight champ Joe Louis as “official greeter.” That may have given Michael hope for a while. Castro nationalized US property, including the hotels and casinos, in August 1960. But, Michael probably would have known from his Mob sources that the CIA was conspiring with the Mafia to get rid of Castro. “Hope springs eternal…”