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alternatehistory.com
I just decided to spitball this...
In April 1961, 1400 Cuban exiles, trained and armed by the CIA, landed at Cuba's Bay of Pigs. I remember reading in a book about the first men killed in the CIA's service that the Eisenhower administration originally greenlit an alternate landing zone on the northern part of the island backed up by direct US air strikes.
I just thought I'd mention that part because if anyone knew more about that, then I'd be willing to pitch it further, and ask what would happen if the Bay of Pigs had been launched with more American-supplied air power, beyond the Alabama Air Gaurd men that flew the B-26s.
Also...Operation Ortsac was a rough battleplan the US had for the invasion of Cuba. I just thought I'd throw up the battleplan:
Cuban Invasion Force (Corps)
US 101st Airborne Division (Secure Jose Martí and Los Banos Airfields)
US 82nd Airborne Division (Secure Mariel and Baracoa Airfields)
US 1st Marine Division (Secure Beaches at Tarará)
US 2nd Marine Division (Secure Beaches at Tarará)
and ask what would've happened had we invaded in, say...the 60s? The 70s? The 80s? or the 90s?