The last we saw of Roth in Havana, he was in a coma, breathing on oxygen, nearly dead from his stroke and the attempt on his life. But he managed to get out on a boat very soon afterward. The most likely explanation is that he was rescued by allies in the Cuban government—perhaps by that smart-looking military contingent that nailed Michael’s bodyguard.

But it seems to me that the military men or other government people couldn’t have known that Batista was going to abdicate that night—and if they did, they’d be far more concerned with saving their own asses, not rescuing an old gringo. And Roth was Batista’s “old friend and associate”—as long as Roth was paying him off. Once he decided to skip, Batista would be concerned with saving his own posterior, not Roth’s. So, I propose an alternate scenario: Roth planned in advance to escape by boat right after the New Year:

Roth’s obsession was to get the $2 million from Michael, and have him assassinated. So, of course Roth denigrated the rebels’ prospects after Michael said they could win—he wanted Michael to feel that his investment in Cuba would be safe. But if Michael, on his first trip to Cuba, saw that they could win, why wouldn’t Roth, an old Cuba hand, know it, too? What’s more, his old pal Batista knew even better that his own days on the throne were numbered: a US State Dept. representative offered him and his family sanctuary in Florida on December 9, 1958, and he probably was hoarding his treasures in preparation for leaving. He may even have warned his old pal Roth to prepare. Batista may not have told Roth that he was planning to split right after the New Year—perhaps Batista wasn’t certain at that point exactly when he’d leave. But Roth figured the Presidential New Year’s party would be an ideal time to line up Michael for execution because he could arrange a seemingly innocent and convenient “ride” for Michael back to his hotel after the party.

So, I’m speculating: Roth planned to get the $2 million, have Michael whacked in a government car on his way from the Presidential Palace to the hotel—and then take off in a boat for Miami. He’d bet that Michael’s murder and his own escape would get lost in the melee of New Year’s Eve in Havana. He’d wait out the aftermath of Michael’s murder, and Batista’s abdication, in the safety of Miami. When the time was right, he’d return to Havana, and his gaming empire, and negotiate a new deal with the rebels.

Roth never got the money, and his stroke disabled him. But his escape plan, meticulously worked out in advance, went forward—and succeeded.

Your views?

Yes, TB, Roth had a plan to escape Cuba because there's always tomorrow. There were probably plenty of people around who wanted to keep Roth alive and free so that they could avail themselves of his money, contacts, and influence including Batista. of course, noone could predict the kind of person Castro would become.

By his hotel holdings, we could assume Roth had been in Cuba for some time; plenty of time to have connections for escape by boat or plane.

Roth would have had no reaon to leave Cuba suddenly after Michael's assassination because he had the backing of Batista. My guess is that they would put out a cover story that the rebel killed Michael, and Roth would make a big deal about how Michael was like a son to him, bla bla bla.

What I think really happened was Roth was on to Michael, and he realized that Michael had plans towould assassinate him. IMHO he faked the stroke (as Michael famously said "he's been dying of a heart attack for the last 20 years" and as Roth famously said he didn't trust doctors who could'nt speak English) and got himself checked into a hospital with specific orders that Batista's guards keep watch over him. Lucky for him they got there just in time.

As all hell was breaking loose and it appeared that Castro was taking over, I believe Roth had enough connections to get himself and his wife out.

Roth was a very well plugged-in person in Cuba. IMO, It is not at all beyond the realm of possibility that he would and did have people that focused solely on getting him out, even with all the chaos going on that night in relation to the changeover in power. For all we know, he probably knew in advance that all that was going down, and had the proper people in place for a contigent need to leave the island.