Joseph Kennedy knew how much Frank longed to be included among and respected by the Kennedy family, and made sure that he used Sinatra as much as possible and tested his loyalty to the extreme in the months leading up to the presidential election.

Looking out for the family, and his son’s reputation, Joe didn’t want any unnecessary controversy or scandals to ruin Jack’s chances of becoming president. When Frank hired black listed communist, Albert Maltz to write a screen play for him, Joe was furious and knew that all he had to do was tell Frank to fire him and it would be done. Joe rang Frank and gave him an ultimatum, ordering him to fire Maltz immediately, pay him off and do whatever he had to, to save face because there was no way that any friend of Kennedy’s was going to be associating with communists, giving America the idea that Jack was partial to communists. He had to choose – it was Maltz or the Kennedy’s. Frank did as Joeinsisted and fired Maltz immediately after speaking to Joe. His incident didn’t sit well among the Kennedy’s very well, as speculation circulated in the media about Jack’s likeness of communists.

When it was announced that Frank was going to be best man at fellow Rat Packer Sammy Davis Jr’s inter racial marriage to May Britt, Joe was again furious at Frank for not realizing what this controvery meant for Jack and his campaign. Joe told Peter to tell Frank that he had to pull out of the wedding, as the campaign didn’t need this controversy so close to the election. Frank, being a close friend of Sammy’s and wanting desperately to earn the respect of the Kennedy family and show his loyalty to JFK was torn as to what to do. Sammy realizing the position that his offer had put Frank in, postponed the wedding until after JFK was named president, allowing Frank to still be his best man, without the worry of what effect his participation might have on JFK or the campaign.

In the 1960 presidential election, in order to be victorious over Republican vice president, Richard Nixon, the Kennedy campaign pinpointed certain areas of the country that could go either way in the election, and they need help securing these areas. In order for Jack to be guaranteed to receive these crucial votes, Joe asked Sinatra to ask Giancana and his mob friends, to help JFK secure supporters in West Virginia and Cook County, Illinois by rigging the election in Illinois to ensure that John would become president. Giancana accepted the favour on behalf of Frank for JFK as Frank realized that JFK couldn’t be indebted to the mob and gladly asked Giancana to help Jack as a favour to him. As a result, JFK became the 35th president of the United States of America.