A Business Plan

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(Pictured: Frank Sinatra, Jr., on stage in 1964.)

Here’s another story involving Frank Sinatra, mostly from James Kaplan’s massive biography.

Twenty-four-year-old Barry Keenan had been a financial and real-estate wunderkind in southern California, but thanks to a disabling car accident, a painkiller addiction, and a divorce, he needed money. So he laid out a meticulous business plan, determining that his best route to success would be a kidnapping. He would invest the ransom in real estate and the stock market, and the profits would get him back on his feet. Within five years, he would return the ransom to the victim’s family, with interest.

He decided that the best potential victim would be a high-profile entertainer’s child, and he had a target in mind: 19-year-old Frank Sinatra, Jr., who was just starting his career as a singer. (Keenan had attended high school with Frank Jr.’s older sister Nancy, and he had even visited the Sinatra home.) On the night of December 8, 1963, Keenan and an accomplice, another classmate named Joe Amsler, snatched Frank Jr. at gunpoint from his dressing room at Harrah’s Casino in Lake Tahoe.

Keenan and Amsler were, honestly, fuckups. They left a gun behind at the scene. They delayed making their ransom demand because they were afraid to talk to the elder Sinatra on the phone. (A third man, John Irwin, older and with a gravelly voice, was recruited to the plot, and he made the calls.) They told Sinatra to go to a gas station and wait for a call with further instructions, but then made several calls before Sinatra could arrive, befuddling the attendant, who—quite rightly—could not understand why somebody kept calling for a famous entertainer who’d have no reason to be there. Imagine the attendant’s reaction when a car squealed to a stop and a man jumped out saying, “My name is Frank Sinatra. Have I had any calls?”

The kidnappers asked for $240,000. Sinatra asked why such a small amount—didn’t they want a half-million or a million? But $240,000 was the precise amount Keenan had calculated in his business plan. Sinatra’s bank arranged the ransom, mostly in small bills. When it was together, an FBI agent asked the bank president how he was supposed to carry it. “Go buy a valise,” the president said. When the agent got to the store, he was $15 short of what the valise cost. So he went back to the bank and was given bills from the ransom money to complete the purchase. Then the kidnappers sent Sinatra on a wild-goose chase to various pay phones before telling him where to drop the $239,985, and how he would get Frank Jr. back. Which he eventually did, on December 11.

In February 1964, the kidnappers went on trial, where Keenan’s lawyer floated a theory she had developed and Keenan approved, knowing it was untrue: that the kidnapping was a publicity stunt to boost Frank Jr.’s career. After making that assertion in open court, a second one followed: there was a “fourth defendant,” a successful singer. Not Frank Sinatra, Sr., but Dean Torrence of Jan and Dean, another high-school classmate of Keenan’s. Keenan had previously hit him up for money, and it was revealed that he’d shown Torrence his business plan in advance.

(The morning after the kidnapping, Keenan actually called Torrence to tell him that “somebody” had kidnapped Frank Jr.. “I never thought he’d do it,” Torrence said later. “I thought somebody else must’ve heard his plan.”)

Torrence and both Sinatras testified at the trial, where the hoax defense quickly fell apart. The defendants were convicted; Keenan and Amsler received maximum sentences, later reduced. Two defense attorneys were eventually indicted for conspiracy and suborning perjury, but the charges were dropped.

Because Frank Jr. was uninjured, and because Irwin released him before his co-conspirators secured the money, suspicion lingered that Frank Jr. had staged the whole thing. Gossip columnist Rona Barrett would put the accusation in print as late as 1974. The Sinatra family believed the whispers hurt Frank Jr.’s career. His sister Tina wrote in a memoir, “Frankie was utterly blameless, but he couldn’t unring the bell.”

Keenan was found mentally ill at the time of the kidnapping, so he spent only about four years in prison. After his release, he went on to become the millionaire real-estate developer he had always hoped to be. In 1988, Keenan told People magazine that he would sometimes bump into Frank Jr. at events and parties in Los Angeles. “We do not speak,” Keenan said. “I respect his space.”

Frank Sinatra, Jr., died in 2016. Coming in the next installment: the story of a song. 

5 thoughts on “A Business Plan

  1. mikehagerty

    The Sinatra kidnapping was the first time outside of fiction (movies, tv shows, cartoons, comic books) that I had heard about a person being kidnapped and held for ransom. I was 8 years old.

    Here’s how much of an imprint that left on me: I live 85 miles from South Lake Tahoe and in the summertime, when it’s 100+ degrees here, it’s the easiest thing in the world for my wife and I to hop in the car and spend the day or the weekend there (we’ll go up in summer, fall and winter, too—it is just stunning).

    Every time I drive by Harrah’s Tahoe—to this day—among the memories are that Frank, Jr. was kidnapped there.

    1. Yeah, the fact that these guys and the drunk driver who killed Jilly Rizzo didn’t (in the words of my favorite Blackadder episode) “accidentally, tragically cut off their heads while combing their hair” has always surprised me.

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