Sinatra invited Kennedy… until plans changed.

Frank Sinatra (biography) would have turned exactly one hundred years old today. My Way, New York, New York, Fly Me To The Moon, My Kind Of Town, I’ve Got You Under My Skin… We still sing along to the hits of The Voice. Born to Italian parents in the impoverished Hoboken, New Jersey, with the bustling Manhattan across the Hudson River, he experienced a captivating life that we can only dream of. In this article, a notorious adventure involving JFK, Monroe, frenzy, pills, drinks, and sex. One day Sinatra invited Kennedy. Kennedy at first accepted, then pulled out and spent the holiday with rival Bing Crosby instead.

– I wrote this article on the day Sinatra would have turned 100, December 12, 2015. Sinatra died in 1998 at the age of 82.

Sinatra was a global singer, a top actor, a womanizer, and much more. What not everyone knows is that Sinatra was a key figure in a vast network of illustrious figures from the 1940s, 50s, and 60s. Singers, actors, models, athletes, politicians, and members of organized crime – they all revolved around Sinatra, and they all came into contact with each other through him. I could write a book full of delightful anecdotes; below, I’ll share one today.

In April 2015, we were in California and visited two homes of Sinatra in Chatsworth, about 50 kilometers north of Los Angeles, and in Palm Springs, near Joshua Tree National Park. And it’s especially the story related to the latter residence that is quite fascinating.

In Palm Springs stands Twin Palms, which Sinatra had built in 1947. The estate is 4,500 square meters. The modern main house has four bedrooms and five bathrooms and was fully equipped with the then very modern air conditioning, a novelty at the time. Cost: $150,000. The construction took seven months and could be completed for the holidays, precisely according to the singer’s wishes. He wanted to host a grand party there.

In the first quarter of 1962, President John F. Kennedy planned a weekend in Palm Springs, California. JFK would stay at the house of his friend Frank Sinatra from March 24 to 26. Sinatra was thrilled: finally, the president would come to his beautiful home. It had been his dream for years. He had, among other things, built special guest accommodations for very important guests and their entourage, installed 25 telephone lines, erected a flagpole with a presidential flag, and even arranged a helipad. People in Sinatra’s circle laughed about it: the singer really wanted to turn it into a Western White House. And now the big moment seemed finally to have arrived.

As the weekend approached, that dream crumbled. Sinatra invited Kennedy, but plans changed. The Kennedys increasingly discovered that Sinatra associated with mob bosses and other underworld characters. Even the biggest crook of that time, Sam Giancana, had been there. The president could never stay in the same house where criminals feasted and drank from the wine… JFK’s brother-in-law Peter Lawford, a friend and an actor colleague of Sinatra, got the thankless task of breaking the bad news to Sinatra. Lawford asked Robert F. Kennedy, the president’s brother and then the Attorney General, to reconsider the decision. “I would break his heart with the news,” Lawford later told a biographer. Sinatra did indeed get angry, slammed the phone, and called Bobby in Washington, DC. The younger brother of the president could only confirm the news. JFK really couldn’t stay in a house where gangsters also frequented. Sinatra was furious and unreasonable. He was incredibly disappointed. With a heavy hammer, one of those things with a long handle, he began to strike the concrete of the helicopter landing pad.

It would get worse. Kennedy did come that way, but he would stay in the beautiful villa of singer Bing Crosby, then the biggest competitor of Sinatra in the music industry. The singer of “Driving Home From Christmas” lived about twenty kilometers from Sinatra, in Palm Desert. Sinatra felt betrayed. As a Democrat, he had done everything for his friend, had greatly helped in the 1960 presidential race. And now Kennedy would sleep in the guest room of none other than a Republican…

Once in Bing’s house, Kennedy called the singer. Sinatra was invited to come over but declined the honor. The relationship was shattered. Sinatra and Lawford hardly spoke to each other and would never act together in a movie again. Later, Sinatra’s family would recount how he was shocked when Kennedy was assassinated. “He stayed in his bedroom for almost a week.”

The weekend in California became memorable for another reason. Bing Crosby himself was not at home, but many other celebrities from the entertainment industry were present that weekend in Palm Desert. It was a fantastic party, according to various sources. Mimi Alford, a young White House intern who later claimed she shared a bed with Kennedy, was also present. “It seemed like a secret club for stars. I had ended up on a different planet compared to what I knew from Washington, DC. Kennedy, of course, was in the center; everything revolved around him. There was alcohol, there were pills, there was sex. I took poppers that night, a very unpleasant experience. That’s why I left for a guest room early.”

Did Kennedy have such a peaceful evening? Not really. On Saturday, March 24, 1962, he was said to have shared a bed with Marilyn Monroe here in Palm Desert. She was one of the guests at the party. There are more stories about romantic evenings, but those are often more speculative. Several reliable sources would later confirm that it indeed happened in Bing Crosby’s house. A sexual encounter between John F. Kennedy and Marilyn Monroe. With Jackie Kennedy 3,500 kilometers away and Frank Sinatra just half an hour’s drive away.

The singer that night, like Kennedy, probably got little sleep.

Back to April, 2015. We visited the house in Palm Springs and drove on to Palm Desert, to Bing Crosby’s house. At the latter house, we were disappointed. We knew that the house was on a compound; you only enter such a neighborhood when you have a good reason. And we didn’t have one… Against our better judgment, we still drove there, armed with a press pass. They were not impressed.