This thread was stimulated by dontomasso’s “Roth’s Vendetta” thread:

If Michael concluded that the rebels could win—and if he planned to have Roth killed before the New Year--why did he have Fredo bring the $2 million to Cuba? The obvious answer: to keep stringing Roth along so he could buy time to identify the traitor in his family. When he found out it was Fredo, he had no further need of Roth—and Cuba. Exit Cuba with the $2 million. Right?

Not so fast. Given Michael’s obsession with becoming legitimate, did he simply plan to write off Cuba altogether? I’m beginning to think he had more plans for Cuba:

While it was obvious that Batista was ruling on borrowed time, Michael couldn’t have known that he’d abdicate exactly when he did. And since tourism was Cuba’s biggest industry after sugar, Michael had to figure that the rebels would keep the hotels and casinos open after they won. (N.B.: Castro didn’t admit he was a Marxist until almost two years after he took power.) And with Roth gone, there’d still be gambling to run, bribes to be paid—and legitimacy to be earned.

So, I’m thinking, Michael planned to step into the vacuum left by Roth’s murder by paying the $2 million or some part of it, either to Batista or Castro, perhaps both. In fact, Michael may have planned to stay in Havana after Roth’s murder and make his move immediately. But Batista’s abdication aborted that plan, and Michael, fearful for himself and his $2 million in the rioting that ensued, took the plane out.

So: If Michael couldn’t have known exactly when Batista would quit, and if he intended to stay in Havana and make his move to become the new gaming czar, why did he have the plane standing by? A long shot: to bring his bodyguard out of Cuba, not him. In Michael’s plan, he wouldn’t need the bodyguard once Roth and Ola were dead. But he had to get the bodyguard out of Cuba lest he be arrested and squeezed by Batista’s thugs, implicating Michael. No bodyguard, no suspect—and no finger pointing at Michael. The authorities—whomever they were—might figure that Michael was behind Roth’s murder, but the $2 million would make them look the other way.