After the disastorus Bay of Pigs invasion, Kennedy lost alot of faith in his military advisors, which is one of the reasons he mulled an invasion of Cuba during the cuban missile crisis, electing instead for a blockade.
During the crisis he was reading a famous history of WW1 called "The Guns of August" he famously said he wanted to ensure there was never a book written called "The Guns of October"
https://www.amazon.com/Guns-August-Pulitzer-Prize-Winning-Outbreak/dp/0345476093/