Michael didn't have to be clairvoyant to figure out that "the rebels could win." Anyone who read newspapers in December 1958 knew that the Cuban dictator was wobbling. The State Dept., early that month, renewed his US passport (he had dual citizenship) and urged him to leave Cuba.

Still, Michael had Fredo bring the $2 million to Cuba. The nominal reason was to string Roth along to buy time so he could find out who the traitor was in his family. But, he took a huge risk: the money could have been confiscated by US Customs (illegal to take more than $10k cash out of the country), or Cuban customs (sticky fingers)--or Roth having his Cuban pals simply seize it. And, given Roth's greed for the money, Michael probably could have continued to string him along without actually bringing the cash to Cuba--Michael knew he had only until shortly after midnight on New Year's Eve to act. He could have figured out something.

So: did Michael give up on Cuba and simply used the money as a ruse? Or, did he have Fredo bring the cash as an advertisement to Batista's successors--including the rebels--that he was willing to pay to play? Castro had not yet declared himself to be a Marxist/Leninist. And Michael might have had reason to think that, no matter who succeeded Batista, they wouldn't close the casinos--tourism and gambling were Cuba's third largest industry after agriculture and mining.

Michael had become the major power in Nevada gaming. Getting Roth's Havana gambling empire would make him being the biggest "legitimate" gaming operator in the Western Hemisphere. I just don't see him giving up on Cuba. Your thoughts?