The Bizarre Story Of Frank Sinatra Jr.'s Kidnapping
On December 8, 1963, 19-year-old Frank Sinatra Jr. heard a knock at his hotel room door. Frank Jr. was preparing to perform a show at Harrah's Lake Tahoe. But when a voice from the other side of the door declared he had a package for the young Sinatra, Frank Jr. opened the door. The "deliveryman" had a gun. He marched Frank Jr. to a waiting car, and the stage was set for the most famous kidnapping in entertainment history.
Frank Jr. didn't know what was going on
Right before that fateful knock on the door, Frank Jr. was in his room at Harrah's Lake Tahoe in Stateline, Nevada. He wasn't alone; he was with a friend called John Foss.
The pair had had dinner together and then retired to Frank Jr.'s room to listen to a tape recording. The singer was waiting to go on stage with the Tommy Dorsey orchestra.
The package was a decoy
When Frank Jr. opened the door, he saw two 23-year-old men staring back at him. There was a package — a wine box stuffed with pine cones — but it had been placed on the floor.
One of the so-called deliverymen took off a black glove and pointed a gun at Frank Jr. "Don't make any noise and nobody'll get hurt," the man said, repeating, "Don't make any noise and nobody'll get hurt."
The sinister plot began
The two deliverymen were Barry Keenan and Joe Amsler. But Keenan was the one in charge. "Both of you get over and lie on the floor, this is a robbery," he told Frank Jr. and Noss. "Where is your money?"
Frank Jr. had only $20 on him, and Noss had nothing. Amsler took the money and seemed ready to leave. "No," Keenan said, "We're going to have to take one of you guys with us."
Stealing Sinatra
"You in the dark hair," Keenan said, making believe that he didn't recognize Frank Jr., "you're going to go with us." They tied Foss up with adhesive tape and made to leave.
Keenan led Frank Jr. out of the room at gunpoint and got him into the backseat of their waiting getaway car. But they knew those ties wouldn't hold Noss forever.
Putting the plan in motion
Keenan began giving orders to Frank Jr. He gave him sleeping pills and put a sleep mask on him. He wanted to make sure the singer wasn't going to pull any funny business. But Junior was cooperative — he worried what would happen to Noss if he wasn't.
But even before the kidnappers got out of town, the police had been alerted and set up roadblocks. Keenan and Amsler were going to have to think fast if they were going to escape.
Moving to the next stage
Keenan figured the police were looking for three guys in a car. So before approaching the roadblock, Amsler got in the trunk. Keenan and Frank Jr. remained in the front of the vehicle. It was Junior who said they could tell the police he'd just had too much to drink.
Amazingly, it worked. They sailed through the roadblock and headed to their safe house. It was only after they'd successfully gotten away that they told Junior that he was actually the victim of a kidnapping.
Getting Sinatra's number
Junior refused to give them the number for his world-famous father — but it didn't matter in the end. News of the kidnapping had spread to every corner of the country, and the kidnappers discovered where Frank Sr. was holed up.
Frank Sr. let it be known that he was waiting at the Mapes Hotel in Reno for any information about his son. The kidnappers enlisted another man, John Irwin, to get in touch with him. It had been two days since Junior had gone missing.
Sinatra was wild with worry
John Irwin was a 42-year-old house painter who was Keenan's mother's boyfriend. He had been enlisted as the ransom contact because he could "talk tough on the phone." But Frank Sr. seemingly didn't want any trouble.
They allowed Senior to speak, briefly, with Junior before getting to business. "What do you want, money?" Frank Sr. asked during their first telephone call. He added, "How much? I'll give you a million dollars if you let my son go!"
They set up the money drop
Surprisingly, the kidnappers didn't ask for $1 million — they settled for $240,000. They called Frank Sr., who agreed to pay the ransom, and told him exactly what to do. It was a complicated plan.
The kidnappers demanded that an FBI courier drive to a series of pay phones to get a new set of directions at each one. Eventually, they would drop a bag with the money in it between a pair of parked vehicles at a gas station on Sunset Boulevard.
Everyone freaked out
What followed was not part of the plan. Amsler and Keenan were supposed to pick up the money and return to the waiting Irwin and Frank Jr. Instead, everybody lost their cool.
Amsler failed to pick up the money and ran away out of fear of waiting FBI. Irwin also freaked out and arranged to drop Frank Jr. back off for Frank Sr. to collect. So it was left to Keenan to retrieve the money, clean out their safe house, and get out of town.
The Sinatra family reunited
As he had arranged with Frank Sr., Irwin dropped Junior off at an overpass of Interstate 405 in California. But Junior was so worried that his kidnappers were playing another game with him that he hid himself away from the road.
Junior was so well hidden that Frank Sr. couldn't find him no matter how much he drove along the street. In the end, Junior fled from the spot to Bel-Air where he managed to hitch a ride to his mom's house.
Everyone was happy... for a while
In the short term, it seemed like everybody had gotten what they wanted. Keena, Amsler, Irwin, and their financier, Dean Torrance, had gotten their money. The Sinatra family had gotten their boy back. It was time to celebrate.
Keenan and Amsler acted like they were in the movies: they lit cigarettes with the bills; they had a fight with bundles of cash; they slept on their ransom. The Sinatras threw a big party, even inviting the media to enjoy the occasion.
Keenan convinced himself he'd done a good thing
Keenan became confident that what he'd done was in everybody's best interests. He decided that he'd use to money to invest in himself and drag his family out of the dire financial situation they were trapped in.
In a round of mental gymnastics, Keenan thought the Sinatra family would be grateful, too. He figured the ordeal would allow Franks Sr. and Jr. to become closer than ever before. But for Keenan at least, the good times wouldn't last.
The FBI gets its men
It didn't take long for the FBI to catch the kidnappers. Irwin revealed the plot to his brother while he was making his way to a quiet spot in New Orleans. Unfortunately, the brother told the FBI.
The rest happened quickly. FBI agents picked up Irwin in short order, and then they later found Amsler playing a game of chess with a friend. They caught Keenan while he was visiting his girlfriend. The FBI got most of the money, too.
Frank gets his money back
The ransom money was only slightly down from the original $240,000 haul. The missing amount had been given to Keenan's ex-wife for furniture. Frank Sr. let her off, saying, "Christ, let her keep the furniture!"
Keenan, Irwin, Amsler, and Torrence were all put on trial for their crimes. The trial lasted just four weeks, and the coverage in the press was extensive. The defense conducted by Keenan also became infamous.
A shocking accusation from the defense
Keenan testified on the stand that the whole thing had been a publicity stunt — with Frank Jr.'s explicit involvement. The elaborate story got so much attention that the rumor stuck to Frank Jr. for the rest of his life.
Yet the hoax theory was proven false almost as soon as it was uttered. The most damning piece of evidence was a confession letter Keenan had written prior to the kidnapping and sealed in a safety deposit box.
Frank Jr. was honest about his involvement
Frank Jr. was surprisingly forthright when it came time for him to testify. He admitted that he told the kidnappers to remove his "FS" ring in case people recognized him and that he once said, "I hope you guys get away with this."
The singer also revealed that he didn't try to escape for fear of his life and that he had no prior knowledge of the kidnapping. Keenan's defense didn't work, and the kidnappers all received jail time.
The sentencing was as wild as the kidnapping
At first, the trio of kidnappers — Torrence got off scot-free — were handed a sentence of 75 years plus life. This was the maximum allowable sentence and that gave the criminals an out: it qualified them for psychiatric evaluation.
"They said in effect that I was legally and mentally insane at the time of the kidnapping," Keenan told the Washington Post in 1998, "and we had no criminal malice, and didn't fit the profile of normal criminals."
They didn't serve that much jail time
This meant that the sentences were reduced to 25 years. Then the defendants sought appeals before the judge found a technicality in one of the psychiatric reports. It cut Keenan's sentence in half again.
In the end, Amsler and Irwin only spent three and a half years in prison before being granted release. Keenan had another 12 months behind bars before getting parole in 1968.
A bizarre post-script
Keenan was able to become a functioning member of society after his time in the big house. He returned to his real-estate roots and worked to build himself a net worth of $17 million by 1983.
When he told his story in 1998, Keenan signed a $1.5 million deal with Columbia Pictures for the movie rights to the kidnapping. Frank Jr. stepped in, though, and successfully blocked the deal in court.
Junior kept quiet about it
This would mark one of the few times Frank Jr. would ever talk about the kidnapping in public. There are few if any records of him discussing the topic after the end of the court case.
You could argue that he never quite got out from under the shadow of his world-famous father. "This family needs publicity like it needs peritonitis," Frank Sr. once told the press.
Junior was seemingly dissatisfied with life
"I was never a success," Sinatra Jr. told The Washington Post in 2006. "Never had a hit movie or hit TV show or hit record. I just had visions of doing the best quality of music."
"Now there is a place for me because Frank Sinatra is dead," Junior continued. "They want me to play the music. If it wasn’t for that, I wouldn’t be noticed. The only satisfaction is that I do what I do well. That’s the only lawful satisfaction."
It wasn't the first time the Sinatras were tied to crime
The press attention on both Franks Sr. and Jr. was par for the course for such a big star. It was a precursor to these days when it’s routine for open secrets about a celebrity’s private life to become tabloid fodder.
In Sinatra’s day, it was his own rumored connections with the mob that made headlines throughout the nation. His link with organized crime was so famous that it even purportedly inspired the character of Johnny Fontane in The Godfather.
Was Sinatra tied to the mob?
The alleged connection apparently began in Sinatra’s early years as a singer. Back then, the only gigs the fledgling star could get were in mob-owned bars and clubs that sprang up in response to strict Prohibition laws. So night after night, Ol’ Blue Eyes would earn his keep entertaining New York’s criminal underground.
Now we know what you’re thinking: playing to gangsters doesn’t automatically make you a member of the mob. Even Sinatra himself made that argument in response to his past. As quoted by Owen Williams on Medium in 2019, the crooner reportedly quipped, “If St. Francis of Assisi was a singer and worked in saloons, he’d have met the same guys. That doesn’t make him part of something.”
Ol' Blue Eyes and the Mafia
But Sinatra’s involvement seemed to grow deeper when he took his first steps towards national stardom. Unhappy with working under bandleader Tommy Dorsey, the musician turned to notorious hood Willie Moretti.
Moretti reportedly “persuaded” Dorsey to reconsider their contract. “Willie fingered a gun and told me he was glad to hear I was letting Frank out of our deal,” Dorsey told Parade magazine in 1956. “I took the hint.”
Helping behind the scenes?
Once he’d earned his celebrity status, Sinatra seemingly became even closer with his wiseguy friends. It was rumored to be the mob who kept the singer from serving in the Army during World War II.
It was reportedly gangster Johnny Roselli who convinced studio heads to cast him in 1953’s From Here to Eternity — a role that helped revive Ol’ Blue Eyes’ ailing career.
A party to remember
Things really came to a head in 1947 when photographs of the star attending a party for mobster Lucky Luciano in Cuba emerged. Sinatra contended that he had been there merely at the behest of a talent agent.
Yet others offered a different story. Actor Jerry Lewis, for example, claimed that he’d been there to smuggle $2 million of mob money back into America. Then again, can you take Jerry Lewis' word for it?
The FBI had a file on him
Sinatra nevertheless carried the rumor of being a made guy everywhere he went. And the press weren’t the only ones who’d paid notice to the Chairman of the Board’s activities either. It had even caught the attention of the United States’ premier crime fighters too: the F.B.I.
The Bureau’s director J. Edgar Hoover opened an investigation into the singer in 1943. But with Ol’ Blue Eyes’ rumored mob connections, their file kept getting bigger. By the time of Sinatra’s death six decades later, his case file was longer than the line to one of his concerts.
“Those were his friends”
Most of these files detailed surveillance jobs against the star. On countless occasions, Bureau agents would watch Sinatra meeting and partying with notorious gangsters. “Those were his friends,” former-fed Sam Ruffino explained to The Gangster Report in 2015. “The fact that they were known hoodlums and murderers didn’t matter to him.”
They may have been his friends, but Sinatra wasn’t above throwing them under the bus to escape injury. Having become aware of his reputation, the singer contacted Hoover in 1950 with the aim of becoming an informant. That year, he also named Moretti and other goodfellas, such as Bugsy Siegel, as friends during an interview with U.S. senators.
Sinatra and the president
In the end, Sinatra’s case history had no real impact on his life or career. Yet it would go on to affect his relationship with President John F. Kennedy. Taking a firmly anti-crime stance, Kennedy and his brother Robert targeted mobsters such as Sam Giancana during their time in power. So obviously spending time with a man with a rap sheet such as Sinatra’s wasn’t good for their image.
As the legend goes, Hoover approached Robert Kennedy shortly after his brother entered the White House. During their meeting, the F.B.I. director showed him evidence that their pal Sinatra was in cahoots with gangsters – including Giancana. When word got back to the President, this was enough for him to sever ties with the crooner for good.
How much did they know?
An interesting theory, yes, but it’s one that has some obvious inconsistencies. For one, Sinatra’s mob ties were an open secret, and his alleged affiliations were plastered across countless tabloid front pages. Surely a man as wise to the world of celebrity as Kennedy would have already known of Ol’ Blue Eyes’ checkered past?
What’s more, it seems that Kennedy may even have knowingly benefited from the star’s mafia connections during his presidential campaign. Reportedly, Sinatra played gigs for Giancana in return for the mobster putting in a good word about Kennedy to union voters.
Two sides to every story
It seems likely then that Kennedy was already well aware of Sinatra’s ties. So if this was the case, what was it in fact that made the President end his friendship with the crooner for good? Well, just like everything in life, it seems there are two sides to every story. And this one doesn’t paint the Chairman of the Board in a very favorable light.
Released in 2018, Lee Server’s Handsome Johnny contained new testimony on the split from Joe Shimon. A former detective based out of Washington, D.C., Shimon was intimately equated with the Bureau and the Giancana case. And as such, he had access to some very sensitive information.
Sinatra and the FBI
According to Shimon, the meeting between Robert Kennedy and Hoover really did take place. But it wasn’t the revelation that Sinatra was linked with the mob that unsettled the President’s brother. Rather it was the content of some of the F.B.I.’s evidence that spooked him — specifically a recorded conversation between Sinatra and Giancana.
Obtained via a tapped telephone, the recording captured Giancana laying into the singer over the issue of government relief. It seems that the alleged favors the crime lord made for Kennedy’s campaign hadn’t been properly repaid. Now he wanted Sinatra to make good on his friendship with the President and get Kennedy to send him some money.
Sinatra and Pat Kennedy Lawford
With his back against the wall, Sinatra began assuring the gangster that he was doing all he could. And to butter Giancana up, the star let him in on his ace in the hole. As Sinatra explained, he was sure to get relief because the singer was having an affair with someone deep within Kennedy’s inner circle: Pat Kennedy Lawford.
The star made it sound like this liaison wasn’t for fun, but rather a ploy to get everything he could from the Kennedys. “[He] made it sound like quite a sacrifice,” wrote Server quoting Shimon. “He vowed he would, ‘sleep with [Pat] until I get something going.’”
"No more White House" for Sinatra
As Shimon continued, “The tapes were played to Bobby, and Bobby went, ‘WHOA…’” Immediately, the Attorney General ran to his brother and told him of this explosive revelation. “And overnight you saw Sinatra out,” Shimon added. “No more White House. No nothing. Shut him off.”
The Kennedy clan cut Sinatra from their lives. But somebody had to pass the message on. Clearly, both Kennedy brothers were too furious to tell their pal that he could no longer fraternize with them. So they left that job to their brother-in-law and Lawford, whose breaking of the news clearly didn’t go down well with his Rat Pack costar.
Lawford’s ejection from the Rat Pack
At the time of Lawford’s visit, Sinatra was expecting Kennedy at his Palm Springs estate. The singer had even had a helipad installed in preparation for the politician’s touchdown in Marine One.
When Lawford arrived instead, Sinatra was lost for words. Reportedly, the star flew into a rage that resulted in some hefty property damage and Lawford’s ejection from the Rat Pack.
Sinatra and Nixon
If Sinatra was hurt by this rejection, then it’s possible that it may have influenced his politics in later life. Although a lifelong Democrat, the singer began swinging to the right when he endorsed Republican Ronald Reagan for governor of California in 1970. Later on, he’d offer his services to Richard Nixon and again to Reagan during their respective presidential campaigns.
But in spite of his break with the Kennedy boys, Sinatra maintained friendly relationships with other members of the family. In 1975 the crooner was spotted having dinner with Jackie — a meeting that may have been more than platonic. According to his friend Jim Whiting, Sinatra claimed that the former First Lady had accompanied him to his hotel room afterward.
The FBI had its benefits
While their intrusive surveillance arguably helped end his relationship with the Kennedys, Sinatra found the F.B.I. an unlikely ally when Frank, Jr. was kidnapped. And as time went on, Sinatra and the F.B.I.’s relationship improved significantly.
It even got to the point where the star was able to gain access to his own files in 1979 and 1980. Thanks to the Freedom of Information Act, Sinatra could see for himself what the bureau’s beef with him actually was. Incredibly, it all started with a crank letter comparing the crooner to Adolf Hitler.
The friendship didn't last
Sadly, Sinatra was unable to rekindle his relationship with Kennedy in the same way. But it seems that if the star had any ill feelings towards the president, they didn’t last long.
During a meeting with Bill Clinton later in life, the star apparently spoke with great fondness about Kennedy. All in all, it seems likely this was a friendship Ol’ Blue Eyes would have given anything to have repaired.