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Face Palm Moments: Some of History’s Most Embarrassing Mistakes

Khalid Elhassan March 23, 2025 16 min

Mistakes - Cain, by Henri Vidal, in the Tuileries Garden, Paris — Cain, by Henri Vidal, in the Tuileries Garden, Paris. Wikimedia

14. How Inaccurate Assumptions Paved the Path for Disaster in Cuba

Cuban exiles practicing parachute drops in preparation for the Bay of Pigs Invasion. CIA

In early 1961, American-trained Cuban exiles opposed to Fidel Castro’s Cuban Revolution trained to invade Cuba and overthrow the bearded strongman and his communist regime. The exiles were convinced – or more accurately, convinced themselves – that Castro lacked widespread support, and that Cuba would erupt in revolt as soon the invasion began. The exiles were also convinced – or convinced themselves – that they would be supported by the US Air Force, and that US Marines would follow right behind them. The aerial cover actually promised the exiles by the CIA was limited support from sixteen WWII era B-26 medium bombers, that were to fly out of bases in Nicaragua. However, that number was halved to eight bombers when the new US President, John F. Kennedy, insisted that the operation be kept minimal.

Written by

Khalid Elhassan

A lifelong history buff, I developed a particular passion for WW2 history as a child, when I spent hours listening to my grandfather, enraptured, as he recounted his wartime experiences in the British East African Campaign and with the British 8th Army in North Africa.

I graduated with a history BA from George Mason University, then went on to get a JD from the University of Virginia School of Law. After lawyering for a decade, I moved to sunny Rio de Janeiro and a less demanding career, opening a tourism agency in Copacabana.

A big chunk of my free time is spent blogging (you can follow me on Quora https://www.quora.com/profile/Khalid-Elhassan ) or freelance writing, mostly about my favorite subject, history.