used Havana as a Rest and Recreation stop for US crews. That may have even been going on at the time of the Spanish-American war, now that I think about it. They did take Guantanamo over a hundred years ago, too.
US military used to take a lot of photos of themselves in Cuban bars with women they picked up for some quality time. Maybe they saw that as their only alternative to drinking torpedo juice in the engine room on the ships.
Calle Ocho! Wow. Oh, I remember hearing wealthy exiles all started fanning out to much more expensive neighbors years ago.
From Wikipedia:
As the new hotels, nightclubs, and casinos opened, Batista collected his share of the profits. Nightly, the "bagman" for his wife collected 10% of the profits at Santo Trafficante's casinos, the Sans Souci cabaret, and the casinos in the hotels Sevilla-Biltmore, Commodoro, Deauville, and Capri (partly owned by the actor George Raft). His take from the Lansky casinoshis prized Habana Riviera, the Hotel Nacional, the Montmartre Club, and otherswas said to be 30%.[56] Lansky was said to have personally contributed millions of dollars per year to Batista's Swiss bank accounts.[57]
More:
https://en.wikipedia.org/wiki/Fulgencio_Batista
(Batista and 2 Americas. You have to guess which one is Batista.)

By Harris & Ewing - Harris & Ewing photograph via Library of Congress, Public Domain
(Pull my finger times 3)
At the beginning of 1959 United States companies owned about 40 percent of the Cuban sugar landsalmost all the cattle ranches90 percent of the mines and mineral concessions80 percent of the utilitiespractically all the oil industryand supplied two-thirds of Cuba's imports.
John F. Kennedy[44]