The nominal reason that Michael had Fredo bring the $2 million to Havana was to keep stringing Roth along so Michael could buy time to find out who the traitor was in his family. But:

--Michael already knew, by the time Fredo arrived, when and how Roth planned to have him killed. So, it would seem, the $2 million didn't really buy him any more time--he knew he'd be dead shortly after the New Year, and had to act before that, whether or not he found out who the traitor was.
--Awfully risky to bring $2 million in cash into Cuba via Fredo if it was just a prop to keep Roth on the hook.

Do you think he brought the money to Cuba for another purpose--i.e., after killing Roth, to see how the dust settled after the rebels took over, and to bribe Castro? At that point, Castro hadn't declared himself a Marxist/Leninist, and Michael might have assumed that, although Batista was on his way out, any successor would still keep gambling going because gambling and the tourism it brought in were pillars of the Cuban economy.
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TB, none of what happened in Cuba was foreseeable by Michael except Roth's planned murder. Once he figured that the rebels could win, he was in a position to tell Fredo to stay home, but he didn't. As you suggest, the money was then available to bribe Batista (after he murdered Roth) ... or Castro. $2 million then was like about $20 million today.

I don't think he ever planned on investing because of the rebels. After seeing the one rebel take his own life with the commander confirmed to him (I think) that Cuba would never be stable enough for him to want to bribe or stay with any rebel in Cuba. Like you say investing that much money would be a HUGE risk when you know Batista is out and you have a rebel leader. I'd imagine most of the casinos were destroyed once the rebels took control as well (which no way we can confirm that of course).

Oli I think Fredo was already on the way when Michael realized the rebels could win.

Michael didn't have to be prescient to realize that Batista was a goner. The State Dept. in early December 1958 knew it and renewed Batista's US passport (he had dual citizenship), and guaranteed him safe passage to America. The news media were all over that story, and especially on Castro's imminent takeover. I'm guessing that Michael believed that the casinos would stay open when Castro won because they were such a big factor in the Cuban economy. And, in any event, I just can't picture him walking away from Havana because taking over Roth's Cuban empire would have made him the biggest legal gambling kingpin in the Western Hemisphere--something he was obsessed with.

BTW: Castro closed the casinos after taking over, but reopened them a couple of months later because the hotel and casino workers' unions protested--their members were out of work. He even hired Joe Louis as the official greeter, and ran newspaper ads in the US claiming that his beef was with the US government, not with the American people, whom he allegedly loved. He didn't declare himself a Marxist/Leninist until about two years after he took over. But, American revelers got the message: stay away from Cuba.

Well TB, that's a question: did Michael intend to bribe either Batista or Castro. Given that Michael went to Cuba and made arrangements to receive the $2 million, he must have intended to bribe one or the other and continue gambling operations there after disposing of Roth.

That's what I'm thinking, Olli. I'm wondering if anyone else agrees?

Well, I'm quite certain that gambling is incompatible with Marxist ideology, as is prostitution, graft, and numerous other forms of corruption (not that they don't happen anyway). So the issue really lies with the question of when it became publicly apparent that Castro's sympathies were essentially of the Marxist persuasion.

It seems to me that Michael Corleone, being nothing if not a savvy (and ruthless) businessman, would surely have done his homework (Tom Haden having played a key role) on Fidel Castro & Company, prior to any serious consideration of a major investment in Cuba - especially given the long history of Cuban civil strife, and the increasingly untenable position of the Batista regime. My sense of it is that he would have given the $2 million to Batista only if he was persuaded that the Batista government was likely to hold onto power, and for a considerable length of additional time.

~ Q

As TB pointed out, Castro's real intentions were not known for a couple of years after he took over and Michael didn't realize that Castro could win until he witnessed the arrest of the rebel.

I was just watching the II scene where Roth tells Michael that the "$2 million never made it to the island." How did he know that? Then, in the very next scene, Fredo drives carrying the the $2 million. Roth knows that also.

Now, besides the obvious question about how Roth knew anything about the $2 million's location, why did Roth conclude (rather plaintively) that the $2 million never made it to the island and why didn't Michael simply tell him that it was on its way?

My guess, Oli, is that Roth probably promised Batista some or all of the $2 million, so he arranged for Batista to have the airport watched, and for Roth to be informed. The Customs guys, looking at Michael's luggage, didn't see the $2 million. Roth also probably arranged with Batista to look out for a short list of Corleone representatives, but none showed up until Fredo arrived. Michael probably didn't tell him that the money was on its way in order to keep stringing him along.

As you know, I believe Fredo was in with Roth and Ola far more deeply than he let on, so it's possible Fredo was in touch with Ola by phone before he arrived, letting him know the status of the $2 million.