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In 1963, a 23-year-old Barry Keenan devised a plot that he believed would make even his wildest fantasies a reality. It was just a few days after the assassination of JFK and America was still reeling. It seemed the perfect time to set his plan in motion. So, with the help of his former high-school classmate, Joe Amslet, Keenan embarked on a criminal venture that would see the pair kidnap one of the most famous young men in America, Frank Sinatra Jr.

While the FBI files on the Frank Sinatra Jr. kidnapping case would have you believe that Keenen was little more than a cash-hungry nut, the reality is far more revealing. By ’63, Keenan was at rock bottom. He was studying at UCLA but had once been a classmate of Nancy Sinatra, the young Frank’s sister. But, while the Sinatra’s had gone on to become international singing sensations, Keenan had wound up addicted to booze and pills following a car accident, an addiction that left him without friends or money. So, when he concocted a plan to kidnap Frank Sinatra Jr., Keenan wasn’t simply motivated by financial strife, (although that was a big part of it) he was also motivated by the unbearable realisation that money and fame were only available to the select few. The American dream, it seemed, was just an illusion designed to disguise the truth.

This plan, Keenan believed, would readdress the balance. Sinatra Jr., who at this time was at the dawn of his career, embodied the absolute pinnacle of Hollywood entitlement and thus seemed the perfect target. However, Keenan’s decision to pick off the young Sinatra was also motivated by empathy. As he recalled in an interview in 1998: “I decided upon Junior because Frank Sr. was tough, and I had friends whose parents were in show business, and I knew Frank always got his way,” Keenan told the New Times Los Angeles in 1998. “It wouldn’t be morally wrong to put him through a few hours of grief worrying about his son.”

With their target identified, Keenan and Joe Amsler began tracking Frank Sinatra Jr., following him to shows in Arizona and Los Angeles with the intention of busting into his dressing room and taking him hostage. Alas, both times, their nerves got too much and they had to abort the plan. Then, Keenan and Amsler were faced with an ultimatum. In ’63, Sinatra Jr. was set to perform in Lake Tahoe, from where he would board a plane to Europe to continue his tour. Knowing that this was their last chance, they drove to the hotel Sinatra Jr. was staying in and asked for his room number at the desk, pretending to be delivery men. Giddy with anticipation, they jogged along the carpeted corridors until they found the room number and turned the handle.

When the door swung open, Keenan and Amsler – pistols loaded – found the singer sinking his ivory-white teeth into a plate of fried chicken. Opposite him sat Bob Foss, a musician in his backing band. A half-nibbled drumstick fell from the trumpeter’s greasy fingers as Amsler held him down and tied him to his chair. Meanwhile, Keenan – with the nozzle of his gun pressed against the singer’s temple – wrapped a band of masking tape around Frank Sinatra Jr.’s mouth to stop him from calling out for help. Leaving Foss in the hotel room, they dragged Sinatra Jr. outside and threw him into the trunk of their car.

While Keenan and Amsler made their way to Los Angeles with Sinatra Jr. in tow, Foss managed to untie himself and immediately called the police. The police, in turn, notified Frank Sinatra. Keenan, aware that Foss would likely make a break for it, made a deal with Sinatra Jr. “I said, ‘Frank, your friend’s going to get up before we get out of Lake Tahoe, and I’m concerned that there’s going to be gunplay,'” Keenan later explained. “‘There’s one way that we can work this out, and that’s if you play along with us, and we pretend that we’re just guys out having a good time.'” Sinatra Jr., not having many other options, ended up submitting, allowing Keenan and Amsler to evade capture despite being pulled over by police.

After driving for 400 miles, Keenan, Amsler and Sinatra Jr. arrived at their LA base, at which point they were met by fellow conspirator John Irwin, who had just called Frank Sinatra and demanded $240,000 in exchange for the release of his son. The FBI, who by this point had liaised with Frank Sinatra and his wife, advised the worried parents to pay the ransom and then allow their agents to track their money and capture the kidnappers. Following this suggestion, Sinatra Sr. gave the money to the FBI, who then photographed it before dropping it off at the agreed location. That’s when things started to unravel for Keenan and Co. While on their way to pick up the money, Irwin, who was little more than a bundle of nerves by this time, decided to release the hostage. After walking around LA in a state of befuddlement for a little while, Sinatra Jr. eventually found a security guard, who agreed to take him to his sister Nancy’s house.

For a while, it seemed as though Keenan and the kidnappers might avoid capture altogether. Sinatra Jr. described his captors to the authorities as best he could, but, being blindfolded, there was only so much information he could give. Eventually, however, Irwin was captured and blabbed on his co-conspirators. At a widely publicised trial, Keenan and Amsler were sentenced to life in prison, while Irwin was sentenced to 75 years.

But, in reality, the trio served but a fraction of their total sentence. Indeed, as Keenan recalled: “They said in effect that I was legally and mentally insane at the time of the kidnapping, and we had no criminal malice, and didn’t fit the profile of normal criminals.” Subsequently, Amsler and Irwin served only three and a half years, Keenan, four and a half. Following his release, Keenan became an incredibly powerful figure in the world of real estate and, in 1999, was offered $1.5million by Columbia to recount the story of the kidnapping on film. However, Frank Sinatra Jr. filed a lawsuit that led to a court ruling forbidding any of the conspirators to profit financially from their crimes, a final victory against a man whose crimes were motivated as much by class anxiety as they were by desperation.

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