Not since President Kennedy has a U.S. president been in such a position to have an impact on Cuba.  

Of course, President Kennedy fumbled on the Bay of Pigs.  He followed that with a better performance in the Missile Crisis but did not force the USSR to take Castro out along with the missiles.    

After that, it really came down to waiting for Castro to die or to get overthrown.  The U.S. was not going to invade a Soviet satellite, and Castro used MiGs and tanks to put down the Escambray rebellion of the late 1960s.  (By the way, my friend Enrique G. Encinosa wrote about this war in exquisite detail.  The translation of the title is The Forgotten War, the uprising against Castro that was brutally crushed town by town.  It was horrific, and someone should be charged with war crimes against civilians.)

President Trump has two choices: he can continue the Obama bailout of Cuba or pull the plug.

First, Cuba is a disaster that no reform can fix.  Spyridon Mitsotakis called it just right in a post recently:

In March of 2014, I spent two weeks in working-class areas of Cuba. I went as a visitor, but was not a tourist. I wanted to see communism for myself — and it was all I feared it to be. 

About a year later, with Obama administration’s embrace of the Castro brothers, I wrote at Brietbart.com about a Cuban worker who explained to me that while they hear endlessly from the government about the “American embargo against Cuba,” the real problem is the “internal embargo” — the embargo that the government elite has imposed on the Cuban people to keep them from participating in the economies of the elite and the outside world.

Again, there is no reform for Cuba except throwing away the entire system and starting again.   

My guess is that Raúl Castro knows that Cuba is beyond reforms.  At the same time, he was willing to go along as long as President Obama participated in a bailout of his regime.  Why not have the foolish "Yánqui" bail you out if you can get away with it?

President Trump should take a different course:

1) Cancel the executive orders and stop everything started under President Obama.  He has a pen, and Congress is not going to lift the embargo.

2) Continue to speak loudly on behalf of the Cuban people.  He could even wear a baseball cap that goes like this: "Cuba sí, Castro no."  He could go farther and call on Major League Baseball to play an All Star Game in Cuba as soon as Castro is gone.

My guess is that Raúl Castro will quickly get the message that it's over.  There is no one ready to bail him out anymore.  Venezuelan oil can't.  China and Russia won't do it unless they are given the keys to the island.  Latin America talks a lot, but those nations have their own problems.

Let Raúl Castro take his millions and move somewhere else, maybe Bolivia.  President Trump then sits down with the next tier of leadership and demands free elections in exchange for ending the embargo.  I think they will listen, because they all know that Cuba is a mess beyond repair.

Could it happen that quickly?  Yes, it can, and no one knows that better than Raúl Castro.

In the summer of 1958, the U.S. cut off military assistance to then-president Batista.  It signaled that it was over, and he left months later.  It cut the ground from under Batista and created the opening for Fidel Castro to come in.

In early 2017, President Trump could do his own version of that Batista play.  He could promise the new Cuban leadership a deal subject to Castro leaving and elections forthcoming.

Am I too optimistic?  I don't think so, and President Trump is in a position to do it.  Pull the plug, Mr. Trump, and you will be given a hero's welcome in Cuba.

P.S. You can listen to my show (Canto Talk) and follow me on Twitter.