On December 8, 1963, singer Frank Sinatra Jr. was kidnapped from Room 417 of the Harrah’s Lake Tahoe resort and held for ransom. Sinatra, who was 19 years old at the time, was released two days later after his father paid the $240,000 ransom demanded by the kidnappers. Frank Sinatra reportedly offered $1 million, but the kidnappers strangely declined the larger amount. Another suspicious incident occurred during the kidnapping. While driving away in the getaway van, the kidnappers crossed a road block that had been setup and ringer leader Barry Keenan was able to talk his way through the police barricade, even though police had been give a description of the van they were driving.

Mastermind Keenan, along with Johnny Irwin, and Joe Amsler, were soon captured. The trio were prosecuted for kidnapping and sentenced to lengthy prison sentences, however only served ten percent of their terms. Keenan was later determined to have been legally insane at the time of the crime and hence not legally responsible for his actions.

In a later interview with Ira Glass, kidnapper Barry Keenan said that he had intended to pay back the ransom to Sinatra’s father. After his release from prison, Keenan later invested in real estate and became multi-millionaire. Many people wondered why – with the well-known connections Frank Sinatra had in the underworld – no retribution was taken on Keenan, Irwin, or Amsler. Another mystery surrounds the ransom money itself. While $240,000 was paid in ransom, only $168.000 of the funds were ever recovered.

The kidnappers demanded that all communication be conducted by payphone. During these conversations, Sinatra’s father became concerned that he would not have enough coins to make the calls, prompting him to carry a roll of 10 dimes in his pocket at all times for the rest of his life. The elder Sinatra was even buried with 10 dimes in his pocket.

At the time of the kidnapping, Sinatra’s father was shooting the Gordon Douglas-directed movie Robin and the 7 Hoods with Dean Martin, Sammy Davis Jr. and other members of the famous Rat Pack. The stress of the kidnapping, in addition to the assassination of his close friend John F. Kennedy just a few weeks prior to the kidnapping, caused Sinatra’s father to seriously consider shutting down the production, although the film was ultimately completed and released on June 24, 1964.