The kidnappers in court (CORBIS)

In 1961, three men, Barry Keenan, Joe Amsler, both 23, and 42-year-old John Irwin, decided they were going to kidnap 19-year-old Frank Sinatra, Jr.  Keenan was the main instigator.  He had gone to high school with Nancy Sinatra, Jr. and had a passing acquaintance with the family.  Like so many of his generation, he was a fan of the “Chairman of the Board.”  Years later he would say, “I liked his music.  His slow songs were always very popular in high school for dancing with the girls.”

Despite his youth, Keenan was an accomplished businessperson.  At the tender age of 21, he had become the youngest member of the Los Angeles Stock Exchange.  He went into real estate development the next year and suffered a sudden financial reversal.

He hit upon kidnapping for ransom as the way to dig himself out of his economic hole.  The first victim he considered was Tony Hope, son of the famous comedian Bob Hope.  Patriotism dissuaded him from this selection.  “Bob Hope had been very active with entertaining the troops and seemed like an all-around good guy,” he said later.  “Kidnapping Tony didn’t seem like a very American thing to do.”

Why pick on the son of Ol’ Blue Eyes?  “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,” Barry explained.  “It wouldn’t be morally wrong to put him through a few hours of grief worrying about his son.”  He even rationalized that he would be doing the Sinatra family a favor by kidnapping a member of it.  The kidnapping, he thought, would bring the family closer together.

Keenan enlisted Amsler and Irwin in his kidnapping plot.  In an interview decades later with Peter Gilstrap of the Dallas Observer, Keenan would say that the trio planned to snatch Sinatra Junior from the Ambassador Hotel in Los Angeles on November 22, 1963.  The reason?  There was a USC versus UCLA football game scheduled for the day after and businesslike Barry believed he could go to the game and establish an airtight alibi.

That day Keenan picked up the phone and heard the switchboard operator sobbing on the line: President John F. Kennedy had just been shot.  That put a monkey wrench in the plan.  Amsler and Irwin, both Kennedy admirers, broke into tears when they heard the news.  Keenan was only concerned with the fact that his own scheme had been derailed.  But only temporarily, he decided.

So Keenan and colleagues followed the younger Frankie to Lake Tahoe where he was scheduled to appear at Harrah’s nightclub.  Together with Amsler, Keenan spirited Sinatra Jr. away from his hotel room and took him across the Nevada state line and into California.  The young singer spent some time as a hostage in a room in the San Fernando Valley with Keenan; captor and hostage chatted even if not in complete comfort.  “He told me of the little money he was making,” Keenan recalled.  Keenan also quoted young Frankie as saying, “I’ll bet the receipts wherever I sing will go up now on account of this publicity.”

Frank Sinatra Snr. talks to the press (CORBIS)

The kidnappers contacted Frank Sinatra, Sr. and demanded a ransom of $240,000.  The legendary crooner coughed it up but most of the money was recovered after Keenan, Irwin, and Amsler were arrested.

John Irwin hired Gladys Towles Root as his attorney.  The story he told her made him sound heroic in a wacky manner.  Irwin admitted that he had been the runner for a bookmaker in his salad days.  He claimed to have had an ethical and spiritual awakening so he settled down to the rigors of a 9-to-5 job and the responsibilities of marriage and family life.  Irwin said that he was enamored of Keenan’s mother and he had developed a fatherly feeling towards her son. Irwin claimed he went along with the plot to kidnap Sinatra only in order to prevent the singer from being physically harmed and Keenan from committing a more serious offense.  Irwin claimed, “I took an oath unto myself that whenever I saw a boy going any or partly astray I would lean over backwards to help him.”        

Root seemed impressed by her client’s earnest desire to aid one wayward youth and “save” a youthful kidnapping victim from serious injury.  Said she of Irwin, “This man is not a criminal type.  His mind is broad and open, and he does not think connivingly.  He is inconceivably naďve.  He believes the Sinatras and his co-defendants are going to do right by him.”

The story that Root, together with Amsler’s attorney, presented to the court would bring screaming fresh headlines and haunt Frank Sinatra Jr. ever after.  The kidnapping, they contended, had been a hoax engineered, in part, by the supposed victim.  The entire business was a publicity stunt intended to jump-start young Sinatra’s career.  Root always referred to Sinatra’s “removal” rather than his kidnapping.

Frank Sinatra Jnr. leaving court (CORBIS)

The jury did not buy it and all three men were convicted.  However, while Keenan and Amsler were given life sentences, Root’s client drew a term of 16 years and eight months.  However, all three men would end up spending relatively little time behind bars.  Both Amsler and Irwin were out after only three and a half years.  Barry Keenan was out after four and a half years.

This case would be an unfortunate “first” for Root.  She would be accused of herself committing crimes on her client’s behalf.  In July 1964 she was indicted on charges of conspiracy, suborning perjury, and obstructing justice in the case.  In 1968, all charges against her were dropped.