For someone who was worth in excess of $100 million at the time of his death, Frank Sinatra was obsessed about dimes. For nearly fifty years, the legendary entertainer, who could purchase anything he wanted, always kept ten dimes in his pocket. The reason for this strange obsession can be traced to one of the darkest days in the great singer’s life.

On December 8, 1963, Sinatra was still in shock from the assassination of his friend John F. Kennedy. When FBI agents asked to speak to him, his first thought was that it had something to do with the tragic events of two weeks prior. Instead, the agents gave Sinatra the horrifying news that his 19-year-old son, Frank Jr., had just been kidnapped.

The teenager was snatched from his dressing room at Harrah’s Club in Lake Tahoe by former high school classmates Barry Keenan and Joe Amsler. Later, they would be joined by John Irwin, and between the three of them, they planned to demand a hefty ransom in exchange for the young man.

The FBI told the elder Sinatra to expect a ransom demand and that he should agree to the kidnappers’ terms. The FBI planned to locate the kidnappers through surveillance and traceable currency. Less than 24 hours later, Irwin called Sinatra and made the demand: $240,000 in cash or he would never see his son alive again. The kidnappers had one other demand. To avoid the risk of phone taps and traceable calls, all future communication would be done exclusively through pay phones.

It was during one of those pay phone calls on December 10 that Sinatra lost contact with the criminals. The reason for the interruption was that he had run out of dimes to feed the phone. That moment was the most terrifying event in the singer’s life. He was horrified to think his son might die because he didn’t have ten cents to slip into a pay phone. Fortunately, he was able to acquire some change and reestablish contact.

Sinatra agreed to drop off the ransom at a specified location. He did so on December 11. Keenan and Amsler went to get the money, leaving Irwin to guard the younger Sinatra. When they did not return when expected, Irwin panicked and released his captive. Frank Jr. walked several miles before finding someone to help him. He was returned, unharmed, to his family.

The kidnappers were quickly located and arrested, and the Sinatra family worked hard to return to a normal life. For the rest of his life, however, the elder Sinatra was haunted by that moment when his phone call was cut off for lack of a single dime. That is the reason why, for the rest of his days, the wealthy entertainer could always be found with ten dimes in his pocket. In fact, he was even buried with those coins reassuringly at his side.

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