Sinatra never really did like Joe, but he liked JFK so that meant that everything Joe wanted on his trips to Sinatra’s Palm Springs compound, Joegot in abundance. The best call girls, the best food, the best of everything – even royalties that Giancana didn’t receive on his Palm Springs visits. On his visits to Palm Springs, Joe Kennedy took a liking to one of Sinatra's favourite call girls at the time, Judy Campbell. Judy would go on to American infamy as the fourth corner of a quadrangle that included Sinatra, Giancana and JFK. But before his son began an affair with Judy, Joe was there courtesy of Frank.

Sinatra had an instinctive hatred of the Irish from his early days in Hoboken, when the shanty gangs were the dago gangs' worst enemies, never to be trusted. Sinatra could never shake his distrust of Joe but fulfilled his every wish in order to become closer to JFK and the Kennedy family.

Joe knew how to play to Sinatra's vanity, as well as to his insecurity. The road to power would be his road to respect, as Frank saw it, so Joe used Frank as much as he could, to benefit Jack’s presidential campaign and election. Sinatra performed at fundraisers during the campaign and personally planned a star-studded inaugural gala after Kennedy’s election. He had the lyrics to his hit song “High Hopes” rewritten to make it Kennedy’s election theme song., with the Kennedy’s benefiting from all his help, and fooling Frank into believing that his connection with the Kennedy family was stronger than it was.

Joe asked many favours of Sinatra, knowing that he wouldn’t turn him down. Sinatra hired black listed communist writer, Albert Maltz to write a screen play for him, that deeply displeased Joe. JFK was associated with Frank, and the fact that Frank was associating with communists reflected badly on JFK and his campaign, giving the impression that Jack was soft on the commies. Joe gave Frank an ultimatum – it’s him or us. At Joe’s insistance, Frank paid off Maltz and hired another writer for the job. Although Frank had done the right thing by the Kennedy’s, the family started to lose their interest in Frank and started questioning whether Frank’s association with the family was beneficial or damaging.

When Sammy Davis Jr. announced his engagement to May Britt, it caused much controversy as inter racial marriages were frowned upon in the early 60’s in America. In addition to the controversy surrounding the engagement, Sammy asked Frank to be his best man. Frank agreed with no hesitation, as Sammy and Frank were very close friends. The fact that Frank was to not only to appear at an inter racial marriage, but be in the bridal party concerned and angered Joe as it was more controversy surrounding Frank that transferred directly to JFK and his campaign, as he was associating himself with a man who was not only hiring communist writers but condoning and participating in an inter racial marriage – both extremely controversial issues at that time. Joe told Peter to talk to Frank and tell him to refuse Sammy’s offer of best man. Frank was furious at Joe for suggesting he pull out of his friends wedding, and angry at Peter for delivering him the news. Sensing the spot that Sinatra was in, Sammy postponed his wedding until after JFK was sworn in as president allowing Sinatra to be his best man.

In the 1960 presidential election, with Kennedy running against Republican vice president, Richard Nixon, the Kennedy campaign pinpointed certain areas of the country that they needed help in securing. Joseph Kennedy asked Sinatra to ask Giancana to help with votes in West Virginia and Cook County, Illinois. This deal with Giancana would guarantee that he would arrange to rig the presidential election in Illinois and ensure that his son John would become president. It was made clear that this would be a favour for Sinatra on behalf of the Kennedys, not a direct favour for JFK or the Kennedy family, as it would be dangerous for the president to be indebted to mob bosses directly. Giancanaagreed to help and used his power in Illinois to ensure that JFK received the crucial votes he needed to be victorious over the election favourite, Humphrey.

In March 1961, Giancana wanted Robert Kennedy to back off from his investigation of his friends, and wanted Frank to talk to Joe about the possibility of Bobby agreeing to do just that. According to a wiretapped phone conversation between Giancana and Johnny Roselli . . . Frank had said to Sam, while they were in Florida, "Don't worry about it. If I can't talk to the old man (Joseph Kennedy), I'm gonna talk to the man (Jack Kennedy)." Frank never got to speak to Joe or Bobby about it, but he did push for Peter to talk to Bobby about laying off Giancana only to be told by Bobby to mind his own business. Bobby was going after Sam with a vengeance and no one was going to stop him. Frank wasn’t at all overly concerned that RFK was to continue his investigations, as Frank didn’t want to jeopardize his relationship with JFK or the Kennedy family by asking for favours for Giancana.