It's one thing when your kidnapper has to borrow gas money from you; it's another when they ask for a ransom so low that the family volunteers to quadruple it.
Keenan needed some seed money in order to forge forward with his plan, so he contacted a friend from University High, Dean Torrence of Jan and Dean fame. Barry actually outlined his plan of kidnapping Frank Sinatra, Jr., to Torrence and did everything short of a white board presentation to explain how Torrence's money would be repaid with interest after receipt of the ransom money. Dean gave his former classmate $500 and later told law enforcement officials that he hadn't thought that Keenan was serious. Barry realized that he'd need help for his caper, so he enlisted high school friend Joe Amsler and a house painter named John Irwin, who had once dated his mother. Barry paid his accomplices $100 per week for their cooperation, which was much more than either was earning in the private sector.
Keenan's original plan was to abduct Frank Jr. from LA's Ambassador Hotel on November 22, 1963. The "gang" paid for a room in the luxury hotel as part of their plan only to be thwarted by the assassination of President John F. Kennedy. Shows were cancelled as a result of the President's death and security was in high gear across the nation. Their last chance was nabbing Junior at his Lake Tahoe gig the following week; after that, he was headed to Europe. Using the last of their original $500, they gassed up their car and headed for Nevada.
THE CRIME, TAKE TWO
Keenan and Amsler brought a special delivery to Room 417. When the door opened, Keenan presented the decoy box to Sinatra. "Put it over there," Junior told them, then he returned to his room service meal. Suddenly Keenan and Amsler produced guns and bound and gagged trumpet player John Foss, who'd been dining with Frankie. Junior was blindfolded and hustled out to the waiting Chevy Impala. During the eight-hour drive to the gang's Canoga Park hideout, they had to borrow $11 from their hostage in order to buy gas. Meanwhile, back at the hotel, Foss had wriggled out of his bindings and had contacted the police.
As is typical in these cases, the more people that are involved means the larger the chance that someone is going to eventually spill his guts. In this case, John Irwin was the one who couldn't resist bragging to his brother that he'd been in on the Sinatra kidnapping. His brother called the cops, and during interrogation Irwin quickly ratted out his accomplices. During their trial, the defense used Junior's "I'm sorry" statement to infer that he'd orchestrated his own kidnapping in order to further his career. Nevertheless all three were convicted, with Keenan and Amsler receiving life plus 75 years and Irwin 16 years. Thanks to the far more liberal parole system of the 1960s, Amsler and Irwin were released after 3 years, and Keenan walked out of prison after serving just under five years. Though Frankie was physically unharmed, the incident derailed his career and he became the butt of endless jokes on late-night talk shows.