J.F.K. and Frank Sinatra
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Sinatra and JFK had everything in common: charisma, talent, power. Sinatra stood in awe of JFK, his heroics and his acclaim. Yet JFK was far more in awe of Sinatra than Sinatra was of him mainly because Sinatra controlled the one thing JFK wanted more than anything else: a collection of the best broads in Hollywood, as JFK had told George Jacobs, that his ambition in life was to fuck all the women in Hollywood. It was this attitude that bonded Frank, also a womanizer, and JFK’s brother in law, Peter Lawford. They were drinking, womanizing playboys and when they got together, the parties were nothing short of unbelievable. Jeanne Martin, wife of Dean Martinis quoted as saying that she didn’t like attending parties at the Lawford beach house, as “the things that went on in that house were mind boggling”. JFK needed Frank if he was going to fulfill his goal. He needed the use of Frank’s contacts, to meet the women and his house to conduct his affairs.

When together, according to George Jacobs, Frank and JFK never discussed politics or issues of national concern, they only discussed Hollywood gossip topics and who sexual linked to who. Sinatra received a phone call from JFKon an irregular basis, but this was mostly to cover the President's favourite topic, Hollywood gossip.

It isn’t doubted that JFK and Frank were friends, but the friendship was easily terminated because JFK had responsibilities to his country and had a reputation to uphold and needed to eliminate anything or anyone who would stain the name he had made for himself and his family. Frank was replaceable as he could always make new friends, and still had brother in law Peter to help him to conquer all Hollywood women.

On the contrary, it has been said that JFK thought Frank was crude and vulgar and had no scruples what so ever, however, he was living the life JFK envied.