In many ways, Frank Sinatra and John F. Kennedy’s friendship seemed destined. Sinatra belonged to a group known as ‘The Rat Pack’ throughout the ’50s and early ’60s. One of the group’s key members, Peter Lawford, was actually married to Kennedy’s little sister. As a result, Sinatra and Kennedy often found themselves in close corners and shared spaces, but it definitely didn’t seem like a problem.

The pair hit it off and really seemed to form a genuine bond with one another. The famous musician and politician’s friendship had its fair share of turbulence, and ultimately indirectly sparked the affair between Kennedy and the talented Marilyn Monroe.

Frank Sinatra’s influence on John F. Kennedy’s presidential campaign 

History101 says when Kennedy announced that he would be running for the presidency, it was clear that Sinatra favored the idea. After all, Sinatra even wrote and remastered “High Hopes”, a whole song that was dedicated to endorsing the politician.

Historically speaking, the presidential election of 1960 was incredibly close. At the time, the country was witnessing a large amount of mob activity and crime. Many people have speculated that Sinatra was able to use his connection to Sam Giancana, Chicago’s notorious mob moss, to help swing votes and win essential states like Illinois to secure the role of president. 

Frank Sinatra and John F. Kennedy’s famous dispute

As soon as Kennedy took office things seemed to get shaky between Sinatra Kennedy. For starters, many mobsters and their affiliates were disappointed with Kennedy and his agenda.

The amount of mob-related convictions had skyrocketed in the short span Kennedy had begun leading the country. This put Sinatra in a bit of sticky situation, but he was able to maintain his connections with his mob friends. 

Sinatra’s social circle wasn’t necessarily always on the up and up, but Kennedy continued to be close friends with Sinatra. The pair planned a weekend together at Sinatra’s home in Palm Springs in March of 1962, but the trip ended up being derailed last minute.

Kennedy’s brother is allegedly the one who convinced him that staying at Sinatra’s place would not be a good look for the President of the United States. However, Sinatra was extremely excited for the trip and made a tremendous amount of accommodations to his home in anticipation of the visit.

Extra cottages, updated phone systems, and a helicopter landing pad were just a few of the renovations Sinatra had arranged for. When he received the news that Kennedy would not be staying with him, Sinatra became furious and immediately cut ties with his old pal. 

What is known about John F. Kennedy & Marilyn Monroe’s affair?

Kennedy didn’t end up staying at Sinatra’s on that fateful weekend in March, but he did still head out to the Palm Springs area. Instead, Kennedy stayed with Bing Crosby, a popular entertainer at the time. It was at Crosby’s home where he allegedly first had his affair with Monroe, according to History101.

Kennedy and Monroe had one last famous encounter in May 1962 on Kennedy’s birthday where the famous singer performed her unique rendition of “Happy Birthday”. The affair between Kennedy and Monroe might have been brief and fleeting but the scandalous story definitely seemed to have left an impact. And it all wouldn’t have happened without the mutual connection to Frank Sinatra.

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