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Today, we’re revisiting a particularly bizarre moment of music history.
It’s hard to explain today just how huge Frank Sinatra was. One could easily compare him to someone like Elvis, or (to be a bit more current), perhaps Lady Gaga.
He managed to have not only a blockbuster music career for decades, but was a sought after actor as well — he appeared in movies from 1941 all the way up to 1995 (with a notable cameo as the singing sword in Who Framed Roger Rabbit).
In fact, Sinatra was offered the role of John McClane in Die Hard — he was in his 70s at the time and turned it down.
All this is to set the stage. It is the early 1960s, and Sinatra was the biggest star in the world (the Beatles were still a couple of years away from eclipsing him, Elvis, and everybody else). Meanwhile, some upper class kid, hard up for cash, decides the only reasonable thing to do is kidnap Frank Sinatra’s 19 year old son, Frank Jr., and hold him for ransom.
Barry Keenan, the budding criminal mastermind, was only 23 years old at the time. Already a successful stock trader with boats and cars to his name, and the youngest member of the L.A. Stock Exchange, he had a bright future ahead. Sadly, that all changed; a car accident left him penniless and addicted to painkillers. Wanting to claw his way back to the top, he calculated that if he could get his hands on some money — $240,000 to be exact — he could make some investments and get back on track.
But where to get the cash?
Ultimately, Keenan decided on a kidnapping, and ideally the child of a celebrity. He initially considered going after Bob Hope’s son, yet decided it would be an un-American thing to do. Frank Sinatra, on the other hand, was a “tough guy,” notorious for getting his way. Keenan reasoned the crooner could deal with a few days of being put through the emotional torment of his son being kidnapped.
But there was another reason, Keenan had been high school friends with Frank’s daughter, Nancy Sinatra, and had spoken to Frank Sr. on several occasions. This would be easy! Spoiler alert: It wasn’t.
Like any good businessman, Barry started looking for investors (after all, he needed cash to fund his heist). He reached out to good friend and Surf Rock superstar Dean Torrance (of Jan and Dean fame), who agreed to meet. And what’s more, Keenan presented him with a three ring binder and detailed plan. Dean could tell right away his friend had hit hard times, even if he couldn’t quite wrap his head around the pitch. The teen idol gave his pal $500 to “get his life together,” not taking his friend or this insane plan seriously.
Financing secured, Barry’s next objective was to hire some muscle. He recruited peer Joe Amsler, an amateur boxer and abalone diver, as well as his mother’s boyfriend John Irwin, a Navy vet. He offered each $100 a week to help lay the groundwork for his plans — they readily agreed, and the heist started in earnest.
Frank Sinatra Jr. had his own budding career at the time, performing shows regularly around the country. While today it might be unthinkable to approach a celebrity of such stature, times were different in the 1960s — more innocent, and certainly less security. The trio of kidnappers first tried to grab Frank Jr. in Arizona but things didn’t seem to be gelling quite right for some reason, so they got nervous and called it off.
Their backup date was a live show in L.A., which unfortunately landed on November 22, 1963, the fateful day President John F. Kennedy was assassinated. Everyone, including the would-be kidnappers, was shell-shocked and devastated. They backed off at the last minute, but were intent on trying again.
This left one final opportunity: Lake Tahoe. December 8, 1963 was Frank Jr.’s last stateside appearance before going on a European tour (out of Keenan’s reach).
Unfortunately, Keenan was out of cash again, so he resorted to hitting up Dean once more, who offered him another $500. And that wasn’t the only wrinkle; John Irwin had lost interest in the plot altogether. Keenan’s other accomplice, Joe, had also lost enthusiasm. After a lot of arm twisting, Keenan took him on a “road trip” to Lake Tahoe — conveniently leaving out the fact that the kidnapping plot was still very much on. After some beer and pills, and some convincing, Joe was back on board. The pair decided to pose as delivery men, knock on the singer’s dressing room door, and get the drop on him.
As one might expect, things didn’t quite go as planned.
Knocking on the door of Frank Jr.’s dressing room, the singer told them to come in and “drop their package on the table.” Thinking they would get him alone, they were surprised to find him eating fried chicken in his underwear, with his trumpet player. (*As we learned from The Maestro in Seinfeld, artists will sometimes eat in their skivvies to avoid getting stains or wrinkles on their stage clothes).
Keenan puts the package down and draws his gun, yelling: “This is a robbery! Give me all your cash!” Junior gave him the $20 he had on him. Pretending like they didn’t know who Junior was, they demanded he come with them and restrained his bandmate with adhesive tape. On their way out, they had told him to “Be cool and don’t move for ten minutes!”
They rushed out to their car, exuberant that they had pulled off the first part of their plan. But it slowly dawned on them that they forgot something, something important, something incriminating: they had left their gun back in the room. Upon backtracking to get it, they witnessed the trumpet player already removing his restraints. Keenan reasoned with him “Just stay still for five more minutes!”
Back in the car, they assured Junior that they would let him out just down the road, still feigning that this was a simple robbery and that they inexplicably had no idea who the singer was. Barry told Junior things would look more convincing if he appeared to be a drunk friend they were taking home, so they gave him some Nembutol and whiskey to wash it down with. The singer assured them they had nothing to worry about, and that he’d play along.
Naturally, it wasn’t long before the trumpet player got free, and called the police. On their journey to flee Lake Tahoe, the group ran into a roadblock. Now how to get out of this?
They reasoned that the cops were looking for three people (two kidnappers and the famous singer), and that they certainly wouldn’t be looking for two! So Keenan convinced Joe to get out and they’d meet him somewhere down the road. By this point, a heavy snow had begun to fall that would soon crescendo into blizzard conditions. Joe, a Southern California boy, was nowhere close to equipped for the weather. He ran headlong into the woods.
Once the car made it to the roadblock, a cop tried to search them. “You don’t need to search us, officer,” Keenan assured them. And unbelievably, they didn’t! Yet as the blizzard conditions worsened, Junior became concerned about Joe. “We better find your friend, he could die,” he told Keenan. So they got out and started calling for Joe. Eventually, Joe came ambling out of the icy white tempest — apparently he had run headfirst into a fencepost and knocked himself out. Keenan, concerned that cops had seen two people in a car which now held three, insisted Joe ride in the trunk the rest of the way to L.A.
Back at the safehouse, they broke the news to Frank Jr. that this was indeed a kidnapping and he wasn’t going anywhere anytime soon. Junior was furious — but as it turns out, the bungling kidnappers needed his cooperation again. They forgot to get his father’s number and had no way of contacting him. When asked for the contact info, Junior told them to, well, “F*^k off.”
Now they were really stuck; an angry and uncooperative hostage, no way to contact Frank Sr., and they short on muscle. Their thoughts turned to their former compatriot-turned-house-painter, John Irwin, wondering if maybe he’d be willing to act as a heavy and sound tough on the phone. He agreed for a $40,000 share of the loot.
In the meantime, Keenan has realized he’s left even more of a trail behind — he neglected to pay his hotel bill and remove belongings from his room. Now he had to return to the scene of the crime and cover his tracks, with money he didn’t have. He called his old pal Dean Torrance one more time. Unbelievably Torrance handed his pal another $500. Later, in court, he would say he almost didn’t believe any of this to be real, that he got caught up in lies and didn’t realize how serious it all was.
After learning of his son’s kidnapping, Frank Sr. wasted no time in reaching out to his many contacts. He was quickly on the line with Attorney General Bobby Kennedy and J. Edgar Hoover, to get the best minds in the country on the case. They also figured out pretty quickly that these kidnappers were rank amateurs and terrible at their job. Frank, Sr. and the authorities set up shop in a hotel and waited.
Although the kidnappers quickly sussed out where to get ahold of Frank Sr, they worried that phones might be tapped. They got the number of a payphone at a local Chevron station and told the harried father to wait for a call from them there. They then called a very pissed off and perplexed Chevron attendant every fifteen minutes asking for Frank Sinatra. Thinking it was a prank, the station attendant said “Listen, pal, Mr. Sinatra is not in the habit of taking calls at this Chevron station.”
Not long after, a frantic Frank Sinatra rushes up to the spellbound attendant, and yells “Have I had any calls?!”
When they finally connected, Frank Sr. offered them a million dollars for the safe return of his son. Unbelievably, the kidnappers turned him down; they insisted on only $240,000.
With a drop agreed upon at a local Texaco station (and dutifully staked out by the feds), the kidnappers all agreed to hold Frank Jr. until they had the money in their hands — possibly as long as several days. But while Keenan and Joe went to pick up the money, Irwin grew nervous and just decided to go ahead and release their hostage.
Despite giving up Junior, the kidnappers were all caught in short order, and there was a circus of a trial. It wasn’t long before conspiracy theorists began alleging that it was all a publicity stunt to drum up interest in Frank Jr.’s career — something the Sinatra family has vehemently denied. Keenan, the ringleader, and his accomplice Joe were sentenced to life plus 75 years. Irwin, the third accomplice, received a 75 year sentence. Between appeals and good behavior, all three were released within 5 years.
Upon his release, Keenan got right back into legitimate business, and soon was back on top. He’s since made an illustrious career in real estate and has become an advocate for criminal justice reform.
Frank Sinatra Jr. died of a heart attack in 2016, leaving behind an indelible legacy of music and further cementing his father’s legend and legacy.
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