Frank Sinatra’s Frightening 48 Hours After His Son Was Kidnapped & Held for Ransom

While the rest of the United States was mourning the death of John F. Kennedy after his 1963 assassination, singer and actor Frank Sinatra was facing another turmoil two weeks after the President was murdered. On December 8, Sinatra’s son, Frank Jr., was kidnapped from his Lake Tahoe hotel where the 19-year-old singer was scheduled to perform.

The mastermind of the kidnapping, Barry Keenan, was a 23-year-old UCLA student who was in grade school with Frank Jr.’s older sister, Nancy. His co-conspirators were Joe Amsler and John Irwin. According to Esquire, Keenan had recently been in a car accident that caused chronic back pain and lead to a dependency on Percodan, muscle relaxers, and tranquilizers. He plotted to kidnap the young Sinatra for ransom so he could get himself out of bankruptcy but claimed after the fact that he always intended on paying the family back.

According to All That’s Interesting, the group originally plotted to kidnap Bob Hope’s son but decided it would be “un-American” so went for someone with a less clean reputation. “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,” Keenan told the New Times Los Angeles in 1998. “It wouldn’t be morally wrong to put him through a few hours of grief worrying about his son.”

In the evening, Keenan and Amsler pretended to be delivering a package to Frank Jr.’s room and found him eating dinner with his trumpet player, John Foss — they were expecting to find him alone so this was the first mishap in their poorly executed plan. With guns in hand, they tied up Foss and led Frank Jr. out of the hotel and into a car. Keenan convinced Frank Jr. to play along and managed to make it past a police roadblock and back to their Los Angeles hideout where Irwin joined them. Irwin was the one who called Frank Sr. to demand $240,000 — apparently the older Sinatra had initially offered $1 million for his son’s safe return so when the kidnappers submitted their lowball demand, police were aware they were dealing with inexperienced criminals.

Sinatra was advised by investigators to pay the money as it would likely lead to the kidnappers whereabouts. On December 11, the FBI dropped off the sum at the designated point. When Keenan and Amsler went to collect the money, Irwin reportedly panicked and released their hostage before they returned. Frank Jr. was picked up a few miles away after walking to Bel Air. He was taken to his mother’s home. Despite the error, the men were somewhat in the clear until Irwin told his brother about the kidnapping while visiting him on his way to a New Orleans hideout. His brother turned him in and the men were arrested the same day.

The three men were found guilty, despite Keenan testifying that the crime was a publicity stunt coordinated with people close to the case, a story that would circle around the case for years after it was proven false. Irwin was sentenced to 75 years while Keenan and Amsler’s sentences of life in prison plus 75 years qualified them for psychiatric observation. “They said in effect that I was legally and mentally insane at the time of the kidnapping,” Keenan said in 1998, “and we had no criminal malice, and didn’t fit the profile of normal criminals.” This conclusion reduced the life in prison terms to sentences of 25 years. In the end, Amsler and Irwin both ended up serving three and a half years while Keenan served four and a half. In 1968, Keenan was released from prison and soon dove into the real estate world making him worth an estimated $17 million by 1983.