Frank Sinatra and The Mob
The early '50s were hell for Sinatra. His popularity slipped; he was no longer the boy wonder idolized by the bobbysoxers. He even lost his singing voice for a time, and his career just about hit bottom. Only his old mob pals would hire him for their clubs. He was also embroiled in a tempestuous relationship with actress Ava Gardner whose career was on the rise while his was sinking lower and lower. When they married in 1951, gossip columnists snidely referred to Sinatra as "Mr. Ava Gardner."
It's widely believed that Gardner was the great love of Sinatra's life. Perhaps more accurately, she was the great obsession of his life. He loved her madly and couldn't live without her, but their fights were legendary, and when they got physical, rooms were trashed and furniture was demolished. When Sinatra and Gardner finally separated in 1953, Sinatra fell into a deep depression. He still loved her and was insanely jealous of any man who was with her. Their Mexican divorce was finally completed in 1957. Gardner dated several men after Sinatra, but she was never married again.
By the early 1960s Sinatra was back on his feet, swinging hard and flying high. His voice had returned, stronger and fuller than before. The dreamboat crooner had transformed himself into a confident, somewhat world-weary, brutally honest saloon singer. A bachelor in his 40s with money, fame and connections, he became the self-appointed leader of an elite group of entertainers who called themselves the Clan. The rest of the world knew them as the Rat Pack. The principal members were singer Dean Martin, singer and dancer Sammy Davis Jr., actor Peter Lawford, and comedian Joey Bishop. As accomplished as each one was individually, when they were together, they took their cues from Sinatra. People started calling him the Chairman of the Board, and they said it with the deep respect afforded a Mafia don.
Throughout his life, Sinatra sought out alliances with powerful men, both in the legitimate and illegitimate worlds. While his "hoodlum complex" led him toward Chicago boss Sam "Momo" Giancana in the early '60s, his power complex brought him into the ultimate circle of power, that of the newly elected president of the United States, John F. Kennedy. Sinatra was close to Giancana, and he wanted to be closer to Kennedy. Behind the scenes Giancana shared that desire because he wanted what no Mafia capo had ever achieved—access to the Oval Office. He saw Sinatra as his conduit. But to have the president's ear, Giancana knew that he would have to give a little to get a little.
In the 1960 presidential election, Kennedy, then the Democratic senator from Massachusetts, was running against the sitting Republican vice president, Richard Nixon. The Kennedy campaign had pinpointed certain areas of the country that could go either way in the election, and they need help securing these areas. The word was passed from Kennedy's father, former U.S. ambassador to Great Britain Joseph Kennedy, to Sinatra: Ask your "friend" in Chicago to help us with West Virginia and Cook County, Illinois. Giancana was willing to oblige, delivering his home turf as well as West Virginia where his outfit had enough sway to influence the election. When Kennedy won, Giancana expected the new administration to show its thanks by getting the feds off his back. Unfortunately for Giancana, it wasn't going to be a simple quid pro quo.
Sinatra had done everything he could to ingratiate himself with JFK. He had performed at fundraisers during the campaign and personally planned a star-studded inaugural gala after Kennedy's election. He had had the lyrics to his hit song "High Hopes" rewritten to make it Kennedy's election theme song. And late at night when the press wasn't looking, Sinatra had shown Kennedy the good life, Rat-Pack style—booze, broads and laughs galore.
Sinatra was living a Jekyll and Hyde existence. By day he was an outspoken advocate for civil rights and social justice. By night he was the bad boy-in-chief of the Rat Pack, personifying every naughty little vice that the American male desired. When the president joined the revelry, Sam Giancana saw an opportunity.
At Giancana's suggestion, Sinatra introduced Kennedy to a fetching young brunette named Judith Campbell. Giancana felt that Kennedy would find her attractive because he thought she vaguely resembled the classy first lady, Jackie Kennedy. Kennedy did find Campbell alluring, and the two had an affair. At the same time Giancana started dating Campbell, but according to his brother Chuck in his book Double Cross, it wasn't because he desired Campbell. Giancana had a habit of wooing the wives and girlfriends of men he wanted to control. It was his way of gaining inside information and showing that he could have anything his target held dear. Giancana's affair with Campbell was brief, but this time the strategy backfired on him.
Kennedy's advisors rightly felt that the president of the United States should not be sharing a bed with a woman who was also dating one of the country's top mobsters, particularly when Kennedy's brother Robert, the attorney general, was working so hard to rid the country of organized crime. Almost overnight the president made a turnaround, dumping Campbell and distancing himself from Sinatra, who was stunned by the sudden cold shoulder from the White House. (Kennedy, it should be noted, did not completely clean up his act as far as extramarital affairs were concerned.) The change in attitude was felt most dramatically when Kennedy, who had planned to stay at Sinatra's home in Palm Springs during a California visit in March 1962, abruptly changed his plans and stayed with singer Bing Crosby, a Republican! Sinatra had even gone to the expense of building an addition on his house to accommodate the president and his staff.
Sinatra was mortified, but Giancana was furious. Wiretaps revealed Giancana's disappointment with Sinatra and his low regard for the singer. When it became clear that Sinatra wasn't going to get him what he wanted, the mobster had no use for him.
Never one to put all his eggs in one basket, Giancana was also courting the CIA at this time, promising to use mob hitmen to poison Communist Cuban leader Fidel Castro. It was all a scam, though, to get huge payments from the government for a service that Giancana had no intention of ever delivering. Giancana was playing them, the same way he had played Sinatra. But apparently Sinatra never caught on because he continued to value Giancana's friendship. It was a friendship that would later cost him big time.