Frank Sinatra was the kind of man who could buy a fleet of Cadillacs, an oceanfront mansion, or—if the mood struck him—probably a small country. Yet for all his wealth, he was absolutely obsessed with something that cost a mere ten cents: dimes. For nearly fifty years, Ol’ Blue Eyes never left home without exactly ten of them jingling in his pocket. Not five, not twenty, but ten. The habit was born not out of superstition, but out of sheer terror—specifically, the kind that strikes when you realize your child’s life might hinge on whether or not you’ve got loose change.

A Kennedy Funeral, an FBI Knock, and a Parent’s Nightmare

On December 8, 1963, Sinatra was still coming to grips with the reality of his friend John F. Kennedy’s assassination just two weeks before. When the FBI came knocking, Sinatra assumed it had to do with Dallas. It didn’t. The agents told him something even more personal and horrifying: his 19-year-old son, Frank Sinatra Jr., had been kidnapped.

Sinatra was not the first celebrity whose family was targeted by kidnappers. The world was rocked when Charles Lindbergh’s son was kidnapped in 1932. That kidnapping, tragically, resulted in the boy’s death. This was very much on everyone’s mind as the authorities raced to solve the crime in time.

The Ransom Game, Pay Phone Edition

The culprits were three not-so-masterminds: Barry Keenan and Joe Amsler, who’d gone to high school with Frank Jr., and their buddy John Irwin. Their plan? Snatch the kid, demand a ransom, and live the high life. In reality, it was the criminal equivalent of a group science project where no one really knows what’s going on.

The kidnappers demanded $240,000 (in 1963 money—that’s more than $2 million in today’s cash). They also insisted that all negotiations be handled through pay phones, hoping to sidestep any attempts to trace the calls.

And then came the moment that scarred Sinatra for life. On December 10, while trying to maintain contact with the kidnappers, Sinatra’s call abruptly cut out. The problem wasn’t the FBI, the mob, or wiretaps. It was dimes. He’d run out. For the richest crooner in America, the nightmare was that his son might die because he didn’t have a measly coin in his pocket. He scrambled to get more change, fed the phone, and—mercifully—was able to resume the call.

The Exchange and the “Oops, We Let Him Go”

Three years later, the grandson of one of the world’s wealthiest men would be kidnapped. J. Paul Getty refused to pay the full ransom that was demanded because he wouldn’t be able to get a tax write-off. Fortunately for Frank Sinatra, Jr., his father had different priorities.

Sinatra delivered the ransom on December 11 at a gas station in Los Angeles. Keenan and Amsler went to fetch it, leaving Irwin in charge of guarding Frank Jr. But when the other two failed to return quickly enough, Irwin panicked. His solution? Just let the kid go. Frank Jr. walked several miles until he found a house in Bel Air where he was able to call for help. Sometimes the best escape plan is your captor being too nervous to do his job.

The FBI swooped in, arrested the three would-be masterminds within days, and Frank Jr. returned home unharmed. Sinatra, though, never recovered from that terrifying moment at the pay phone.

Why Dimes Became Sinatra’s Security Blanket

From that day forward, Sinatra carried ten dimes everywhere. Ten dimes equaled one dollar—a small price to pay for never again being caught short when his family’s life might depend on a pay phone. The habit lasted the rest of his life. And in true Sinatra style, he had the last word on the matter: when he was buried in 1998, those dimes went with him.

What Happened to the Kidnappers

Barry Keenan, the so-called “mastermind” of the plot, Joe Amsler, and John Irwin didn’t exactly ride off into a glamorous underworld career. Instead, their caper collapsed almost as soon as it began. Irwin, rattled by guilt and nerves, confessed to his brother, who promptly tipped off the FBI. Within days of Frank Jr.’s release, all three were arrested. So much for their criminal empire.

In 1964, the trio went on trial in Los Angeles. The prosecution had an easy time: the ransom money was recovered, the confessions were plentiful, and the defense strategy was… let’s call it “creative.” Keenan’s lawyers claimed he was too high on painkillers and booze to be legally responsible for his actions. The jury was not impressed.

Keenan and Amsler were sentenced to life plus 75 years, while Irwin received 75 years. In reality, none of them served anywhere near that. Appeals, retrials, and the quirks of 1960s sentencing laws meant that all three were out by the 1970s. Keenan later reinvented himself as a wealthy real estate developer. After all, if you bungle a felony, the logical next step is property speculation. Amsler kept a low profile after his release, and Irwin largely faded into obscurity.

The kidnapping remains one of the oddest celebrity crimes of the 1960s: amateurish, short-lived, and strangely anticlimactic. The crooks ended up remembered less for their criminal genius and more for providing the backstory to Frank Sinatra’s pocket full of dimes.

A Pocketful of Caution

So the next time you hear Frank Sinatra croon about love, loss, or luck, remember: behind the tuxedos, whiskey, and swagger, the man carried ten dimes like a talisman against chaos. It was the cheapest insurance policy in showbiz—one that came with its own jingle.

---