The story goes that on Sunday, December 8, 1963 1963, Frank Sinatra’s 19 year-old son, Jr was led out of his Lake Tahoe hotel room at gunpoint by mobster Barry Keenan before being locked away for four days during which Keenan and his two associates extracted a $240,000 from the elder Sinatra.

Keenan & co got their cash alright, but while they were collecting Sinatra Jr made his escape and walked from their Los Angeles hideout to his Bel Air home, unscathed. A widely reported case at the time, now,a new Wondery podcast, 

, tells the caper from the perspective of Keenan who was eventually caught and served time for the scheme.

It isn’t all movie-of-the-week mobster stuff, either. In the first episode Keenan talks about his own and his mother’s struggles with mental illness and drug addiction.

“I actually rode my bicycle into a busy intersection in the hopes that, if it was God’s will, I’d get run over and go straight to heaven,” he says.

As an adult he became addicted to painkillers and struggled to fund his habit. When God spoke to him through his car radio he concocted the plan to kidnap someone. Aged just 23, Keenan was about to take a desperate step.

Like father, like son: Frank Sinatra and Frank Sinatra Jr.


“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.”

Keenan knew he couldn’t pull it off alone so he recruited his high school friend Joe Amsler and his mother’s former boyfriend John Irwin. The trio began studying Sinatra Jr’s movements and after a few abortive attempts they learned that Sinatra Snr would be playing in Lake Tahoe, Nevada before travelling to Europe. If they wanted to snatch the star’s offspring, this would be their last chance.

Keenan and Amsler entered Sinatra Jr’s hotel room at 9am, posing as delivery men. Jr was hanging out, eating a sandwich with trumpeter John Foss. Keenan pulled out a gun. Then they tied Foss up and bungled Jr outside to a waiting car, telling him to play along to avoid a clash with police.

“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 told the New Times Los Angeles. “‘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.’“

An agent guards the  hotel room in Lake Tahoe from which Sinatra Jr. was snatched


Foss had indeed got loose and called the police before Keenan and Amsler had left the building. Despite this, they managed to travel 400 miles to a Los Angeles hideout with Sinatra Jr complying with their demands in a bid to save his own life.

Once safely secluded in Los Angeles, the criminal duo called Irwin and Irwin put the call through to Sinatra Sr demanding $240,000 for this son’s life on December 10th.

The next morning the FBI dropped the money off at the specified location. Keenan and Amsler picked up the money without a hitch. But, waiting back at their HQ Irwin was beginning to get cold feet and decided to free Sinatra Jr. Jr walked to Bel Air and found a security guard to drive him to his mother’s home.

Keenan’s plan had always been to release Sinatra and, with the money collected, it seemed they had got away with it. Not that the authorities weren’t desperately searching for them.

“It was very surreal, knowing that I was the most wanted person in the country,” Keenan recalls in the trailer for 

The fatal flaw came when Irwin visited his brother in San Diego and spilled the beans. His brother snitched, called the FBI and all three members of the gang were captured the same day with almost all of the ransom money being recovered.

Sinatra Jr. and his mother, Nancy, embrace following his escape


The trial began on February 10, 1964 with Keenan’s defence being that the crime was a publicity stunt coordinated with people in the Sinatra camp. It’s a rumour that persists to this day. Ultimately, however, the story was deemed a lie by the authorities and Keenan and Amsler were both sentenced to life in prison plus 75 years while Irwin was sentenced to 75 years.

Keenan was eventually released from prison just four years later in 1968. After getting into the real estate business he amassed a fortune of some $17 million by the earlier 1980s. A few years later he sold his story to the Los Angeles Times while plans for a feature film were blocked by Sinatra Jr.

Now 81, Keenan is keen to tell his story. He claims that Sinatra Sr put out multiple hits on him, including having someone shoot at him while he was on the beach.

“The guy who was shooting at me on the beach, in Huntington Beach. He had me dead to rights in his scope,” 

 recounts Keenan as saying, “and his colostomy bag broke and caused him to miss me. He fired off a couple more shots, the sand popping up in front of me, so I just ran.”

For more bizarre stories in this larger than life saga we strongly recommend you pour yourself a strong drink and dedicate some time to getting the dope from the horse’s mouth.

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