Check out "Little Man: Meyer Lansky and the Gangster Life." Lansky lost a lot of money in Cuba and never recovered from the loses. He was not that rich by the time he died. He was at his peak by the time of Cuba, but lost hugh when Castro took over.

Luciano was indeed getting money from the States when he was in Italy, but once Costello was no longer boss and Genovese became boss, that money stopped completely.