Singer and film star Frank Sinatra (1915-1998) grew up poor and lower class in Hoboken, New Jersey. Once he made it big in showbiz (thanks to help from his Mafia cronies), he obsessed about fitting in with the upper class. He wormed his way into politics, using his Hollywood star power to campaign and fundraise for Democratic heavyweights such as Franklin Roosevelt and John F. Kennedy. In attaching himself to men of honor, Sinatra hoped to achieve the respectability he craved.
Sinatra had cultivated a relationship with President Kennedy through movie star Peter Lawford, who was married to the president’s sister, Pat.
In March 1962, the president was scheduled to fly to Southern California. Peter Lawford asked Sinatra to be the president’s host at his Palm Springs estate. Sinatra was thrilled. He went straight to work. At his own expense, Sinatra installed a helicopter pad, cottages for the Secret Service, and even a flagpole for the presidential flag.
But the president’s brother Bobby Kennedy wasn’t having it. He was the Attorney General of the United States at the time. When he heard about his brother Jack’s proposed stay at Sinatra’s, he went ballistic. Bobby was making the “most single-minded attack on organized crime in American history” and could not abide Jack associating with someone with mob connections. (1) Peter was the one chosen to tell Sinatra that the president would not be staying with him.
Sinatra did not take the news well. He had a notoriously explosive temper:
“Sinatra vented his spleen by destroying the concrete landing pad with a sledgehammer. He applied a different kind of sledgehammer to his friendship with Peter and Pat [Lawford], banning them from his company….Jack ended up staying at the home of Bing Crosby. Marilyn Monroe flew down to be with the president, spending the night in his bedroom….”
…and Frank Sinatra became a Republican.
(1) Leamer, Laurence. The Kennedy Women: The Saga of an American Family. New York: Fawcett Books, 1994.
For more on Sinatra, check out “Sinatra: Pants on Fire!”