I don't worry about Trump handing over Gitmo but he has said that he wants to get in there and start developing the place and building the Cuban economy.
For a free nation that's a great thing but building the economy of a communist nation doesn't do squat for the people. It just builds a communist government which in turn oppresses the people more effectively.
One of the reasons the Mob was thought by some to be behind JFK's assassination was the failure of the Bay of Pigs, largely on a call to withhold the air strikes which would have eliminated the Cuban air force on the ground, and could have taken out the columns of tanks used against the invading expatriate counterrevolutionaries. Basically, Kennedy left them swinging, and the invasion failed. When Castro had taken over, the Mob lost the significant income from resorts, casinos, and other operations on Cuban soil. Had the Bay of Pigs invasion been supported and successful, and the Communists overthrown, there is a significant chance they would have regained that revenue source. So, basically, Kennedy had destroyed that prospect by withdrawing support from the invasion
while it was in progress.
That aside, 'normalization' of relations with a communist country would have great potential for income properties for a developer (or cronies).