When Frank Sinatra Jr Was Kidnapped And Held For Ransom
- Daniel Holland
- Dec 8, 2022
- 7 min read
Updated: Dec 10, 2025
On the evening of December the 8th, 1963, America was still living in a kind of suspended grief. President John F. Kennedy had been assassinated less than three weeks earlier. Television networks were replaying his motorcade, the funeral procession and the muffled shock on the faces of ordinary Americans. Against that backdrop of national unease, another headline appeared, smaller yet still jarring: Frank Sinatra’s son kidnapped.
The drama did not reshape American history, but it gripped the public imagination instantly. The famous singer’s nineteen year old son, Frank Sinatra Jr., had been abducted from a Lake Tahoe hotel. The crime seemed both theatrical and senseless, carried out not by hardened criminals but by three young men who treated their plan more like a college prank gone horribly wrong. What unfolded over the next few days was a story of panic, improvisation and a brush with tragedy that the Sinatras never forgot.
Junior A Rising Performer Living Under a Familiar Shadow
Frank Sinatra Jr., born in 1944, had only recently started to build his own career. He inherited his father’s phrasing and natural musicality, but he worked hard not to trade solely on the family name. Those close to him often described him as serious and disciplined. One musician later said,"Junior wanted to earn it. He didn’t want anyone thinking he got an easy ride."
By late 1963, Sinatra Jr. was touring internationally with a well regarded band. He was playing theatres, nightclubs and casinos, refining a polished stage presence that surprised audiences expecting a lightweight version of his father. The Lake Tahoe date at Harrah’s Club Lodge was simply another stop on his schedule.
He had no idea that three men from Los Angeles had been following him for weeks.
A Plan Born From Delusion, Desperation and Amateur Confidence
Barry Keenan, the driving force behind the kidnapping plot, was only twenty three years old. He had struggled with drug dependency, financial insecurity and bouts of grandiosity. In later interviews, he insisted that he planned the kidnapping methodically, even describing it as a kind of entrepreneurial scheme.
Keenan wrote in his notes:"If anyone can afford to lose the money, Sinatra can."
He recruited two acquaintances: Joe Amsler and John Irwin. All had attended high school with Sinatra Jr.’s sister Nancy, though none were close friends of the family.
Their first idea was to kidnap the son of Bob Hope. According to Keenan, this was rejected because it felt "un American" to target a man known for entertaining US troops. Frank Sinatra, though admired, did not evoke the same patriotic shield in their minds. It was the sort of confused moral reasoning that defined the entire operation.
Failed Attempts in Arizona and Los Angeles
Their early attempts to seize Sinatra Jr. collapsed almost instantly. They followed him to Phoenix, rehearsing a scenario in which they would burst into his dressing room and spirit him away. When the moment came, Keenan froze.
"I realised how crazy it was," he later said. "I could not move."
A second attempt in Los Angeles also ended in failure when they lost their nerve. Still, they convinced themselves that the timing was slipping away. Sinatra Jr. was due to leave for Europe in mid December. Lake Tahoe would be their final chance.
Wearing delivery uniforms to appear official, Keenan and Amsler walked boldly into Harrah’s Club Lodge on the night of the 8th of December and asked for Sinatra Jr.’s room number. The hotel staff, accustomed to performers receiving deliveries, offered no resistance.
Keenan later described the walk down the corridor as"the longest hallway I ever walked. Every step was a chance to turn around, but we kept going."
The Moment The Door Opened Fried Chicken, Confusion and A Gun
Inside the room, Sinatra Jr. was finishing a late meal of fried chicken. His trumpet player, Bob Foss, sat opposite him. The scene was almost homely. When the door swung open, Foss looked up just in time to see two men enter with pistols drawn.
The drumstick slipped from Foss’s hand."I thought at first it was a joke," he later said, "but the gun was shaking, and that told me everything."
Amsler tied Foss to a chair with tape. Keenan grabbed Sinatra Jr., pressed a gun against his temple and taped his mouth shut. Within seconds they marched him down the corridor and out of the hotel.
Foss freed himself minutes later and alerted security. Police arrived almost immediately, but the kidnappers were already speeding away with Sinatra Jr. locked in the boot.
When Frank Sinatra Sr. was notified, he was in a recording studio. One associate recalled,"He went pale. He kept saying, 'My boy. My boy.'"
A Deal in the Boot Pretend We’re Men Having a Good Time
As they drove into the mountain roads away from Lake Tahoe, Keenan realised that Foss escaping meant they would likely be stopped. He leaned into the boot and made an extraordinary request.
He later recalled saying:
"Frank, your friend is going to get loose, and the police will come after us. I don’t want anyone hurt. If you cooperate, we can get through checkpoints by pretending we’re just men on a trip."
Sinatra Jr., terrified and with no safe alternative, agreed. His composure saved his life. When the kidnappers were pulled over for speeding outside Tahoe, the officer saw three nervous young men in the front seat, none of whom seemed violent or intoxicated. He did not check the boot. They were allowed to continue.
It was the closest the case ever came to ending in disaster.
Arrival In Los Angeles And A Nerve Shredding Ransom Call
After a drive of approximately 400 miles, the group reached their Los Angeles hideout. Irwin, who had spent the evening struggling with anxiety, placed the ransom demand call. He asked Frank Sinatra Sr. for $240,000 dollars.
The singer agreed instantly."I would have paid anything," Sinatra later said.
The FBI advised him to cooperate fully. Agents photographed the ransom notes, catalogued the cash and prepared for surveillance. Publicly, the authorities minimised the risk. Privately, they feared that the panic of the young kidnappers made the situation dangerously unpredictable.
A small footnote from this period developed into a minor cultural myth. It was said that Sinatra, while phoning the kidnappers, asked an FBI agent for ten cents because he had no coins left for the payphone. Although often repeated, the story is slightly exaggerated, but it matches Sinatra’s well known habit of carrying change for quick calls during that era. It became symbolic of his desperation.
The Plot Unravels And Junior Walks To Safety
As Irwin drove to collect the ransom money on the 10th of December, his panic overwhelmed him. Without warning his accomplices, he decided to release Sinatra Jr. He drove the young singer into Bel Air, let him out of the car and sped away.
Sinatra Jr., disoriented after two days blindfolded, walked the streets until he encountered a security guard who recognised him. The guard drove him to his sister Nancy’s home.
Irwin, meanwhile, confessed everything to his brother, who telephoned the FBI. Within hours, agents arrested Keenan and Amsler, they were found still in possession of the entire ransom.
Conspiracy theories erupted almost immediately. Some insisted it was a publicity stunt. Others claimed the mafia staged it. One rumour suggested Frank Sinatra Sr. arranged the kidnapping to bolster his son’s fame. Keenan dismissed all such theories, saying simply,"People gave us far too much credit. We were just idiots."
Trial, Public Frenzy And Unexpectedly Short Sentences
At their 1964 trial, the three kidnappers faced intense media scrutiny. Keenan and Amsler received life sentences. Irwin received seventy five years. Yet the actual time served was surprisingly brief.
Keenan later said,"They decided that I was legally insane at the time, and that we did not fit the profile of hardened criminals."
Amsler and Irwin served roughly three and a half years. Keenan served four and a half.
The Sinatra family never publicly criticised the leniency, but those close to them often said that Frank Sr. viewed the event as a wound that never completely healed. One longtime friend noted,"He was not a man who forgave easily, and he never forgot this."
The Strange Hollywood Epilogue
After his release, Barry Keenan built an unlikely second life as a wealthy real estate developer. In 1999, Columbia Pictures offered approximately 1.5 million dollars for his story.
Frank Sinatra Jr. immediately filed suit under the Son of Sam law, which prevents criminals from profiting from their crimes. A judge ruled in his favour. No film adaptation could proceed if Keenan received payment.
Keenan later conceded:"It was probably the right judgment. We inflicted enough harm already."
Sinatra Jr., for his part, rarely spoke publicly about the kidnapping. He resumed performing, maintained a steady touring career and often acted as archivist and musical director for his father’s legacy. Though he handled the incident with dignity, friends have said that it affected him more deeply than he ever let on.
Legacy A Crime That Could Have Gone Terribly Wrong
The kidnapping of Frank Sinatra Jr. remains one of the most unusual crimes of the early 1960s. It was a plot carried out by amateurs who lacked the ruthlessness normally associated with such acts, yet the danger was real, and the outcome could easily have been catastrophic.
Set against the sombre national mood following the Kennedy assassination, the story struck Americans as surreal. It was a reminder that even the most famous families were not immune to chaos.
Frank Sinatra Sr. later said privately that it was the worst night of his life. For the rest of his days he carried 10 dimes with him at all times, just in case he needed change for the payphone again. He was even buried with a roll of dimes in his pocket.
Sources
https://www.esquire.com/entertainment/a37106130/frank-sinatra-jr-kidnapping-barry-keenan-true-story/
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