When famed entertainer Frank Sinatra died in 1998, he left behind a legacy of success met by few others. Fans bought, reportedly, more than 150 million copies of his albums, making him one of the most popular singers of his era and, for that matter, of all time. He earned 11 Grammy Awards along the way and was also a talented actor, winning the Oscar for Best Supporting Actor in 1954. And with fellow entertainers DeanMartin, Sammy Davis Jr., and the rest of the “Rat Pack,” Sinatra helped establish Las Vegas as one of the world’s premier entertainment destinations.
But Sinatra’s life wasn’t all joy and happiness; no one’s is. In Sinatra’s case, though, a moment of terror stuck with him for his entire life and beyond — and it’s why he took his last dollar with him when he died.
In December of 1963, Sinatra’s son, Frank Jr., was an up-and-coming singer in his own right. Then 19-years-old, Frank Jr. was performing at Harrah’s casino and hotel in Lake Tahoe, on the Nevada/California border. On the night of December 8th, two men, Barry Keenan and Joe Amsler, were there to see the younger Sinatra, but they weren’t fans. Keenan and Amsler were would-be criminals who were about to attempt one of the biggest crimes of the century: they were going to kidnap Frank Sinatra’s only son. Per the FBI, “at around 9 p.m. [Sinatra Jr.] was resting in his dressing room with a friend when Keenan knocked on the door, pretending to be delivering a package. Keenan and Amsler entered, tied up Sinatra’s friend with tape, and blindfolded their victim. They took him out a side door to their waiting car.” The caper was on.
The kidnappers knew that the elder Sinatra had a lot of money and figured, correctly, that he’d pay handsomely to have his son released unharmed. That required getting into contact with Sinatra, and for the kidnappers, that came with the risk of their location or identities being disclosed. For some reason, Keenan and Amsler, along with their third co-conspirator John Irwin, insisted that all conversations take place via payphone, perhaps to make it harder for authorities to trace the calls.
That precaution wasn’t all that effective, ultimately. The trio demanded $240,000, the equivalent of more than $2 million today. The FBI urged Frank Sr. to pay the ransom and use that as bait to catch the criminals, and the plan basically worked. The write-up on the FBI’s site continues: “While Keenan and Amsler picked up the money, Irwin had gotten nervous and decided to free the victim. Sinatra, Jr. was found in Bel Air after walking a few miles and alerting a security guard. To avoid the press, he was put in the trunk of the guard’s patrol car and taken to his mother Nancy’s home. [. . .] Meanwhile, with the FBI’s progress being recounted in the press, the criminals felt the noose tightening. Irwin broke first, spilling the beans to his brother, who called the FBI office in San Diego. Hours later, Keenan and Amsler were captured, and nearly all of the ransom was recovered.” A happy-ish ending for everyone but the bad guys.
The trauma of almost losing a son, though, stayed with Frank Sinatra. For the rest of his life, he carried with him $1 in dimes. His daughter Tina explained why to Larry King (via the Associated Press): “He never wanted to get caught not able to make a phone call. He always carried 10 dimes.”
When Frank Sr. passed away in 1998, his family made sure that those dimes would never leave him. As Smithsonian notes, “The ‘My Way’ singer was buried his way, with a bottle of Jack Daniel’s whiskey, a pack of Camel cigarettes, a Zippo lighter, and a dollar’s worth of dimes.”
From the Archives: Why (Some) Coins Have Ridges: You know, like dimes.