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?

TB, I think Michael was playing all the angles you identify. He had nothing to lose by doing so. I do beleive that Castro had indicated that, once in power, he would allow the casinos to stay in business. noone knew Castro's real plans.

Oli, Castro shut the casinos and brothels right away. But, within a month, the casino and restaurant workers' unions demanded that he reopen them (not the brothels). He did, for a while. Even hired Joe Louis as "official greeter." Newspaper ads at the time emphasized that the "Cuban Revolutionary Government" had "differences with the US Government, not its people." Sure. The people stayed away in droves."

There has always been a part of me that thinks Michael may have been testing Fredo with the suitcase full of cash. At that point, Michael was not entirely certain the identity of the traitor. If you remember, Michael appeared relieved and appreciative that Fredo made it to Cuba with the cash... as anyone would under the circumstances. Many things could have gone wrong as TB stated above but it seemed Michael expressed more of a genuine relief to see Fredo.

If there was true malice in Fredo's heart - what would have stopped him from taking the money and running? In 1958, Fredo could have disappeared and lived pretty well with 2 million dollars. Granted he would have to go far away and out of the country - Asia, Australia, etc. Europe would not even be an option... Corleone contacts would have found his location rather quickly. It's almost as though Michael was willing to spend the 2 million to expose the traitor - no matter who it was. By the way - what became of the suitcase of cash?

Dear God, I just looked at $2 million in 1958 is equivalent to almost $15.5 million now.

Yikes.

If you view the New Year's Eve party scene carefully, as Michael gives the signal to his bodyguard to go kill Roth, you can see Manolo slipping out a side door with the suitcase.

You know Woltz, that's one of Manolo's few scenes that made it past the editors and didn't end up on the cutting room floor. I wish there were more.

I think Michael brought the money in to string Roth along. He knew Roth had planned to killl him, and in turn he tried to kill Roth. My guess is his plan may have been to buy into the Cuban Casinos on his own, but by the manner in which he fled, I cannot agree he ever believed he would be doing business with Castro. Whether he should have known it or not, it was not until he got to Dodge, and probably didn't care about where the 2 million went. As for the risk at U.S. and Cuban customs, I am sure appropriate palms were greased in advance.

It was also quite helpful in revealing that Fredo was the traitor. How else would Roth know the money made it to Havana?