On December 8, 1963, 19-year-old Frank Sinatra Jr., son of legendary singer Frank Sinatra, was kidnapped from his hotel room after performing a show in Lake Tahoe. Sinatra's kidnapper, Barry Keenan, was an alcoholic, drug addicted businessman who was severely down on his luck.
Keenan was from a wealthy family and he actually had moved in the same circles as Nancy and Frank Sr., having met them previously more than once. Keenan was, at age 21, viewed as a business wunderkind, having been the youngest member of the Los Angeles Stock Exchange. Yet Keenan was involved in a bad car accident in 1961, which led to his becoming addicted to Percodan and alcohol. In fact, Keenan was so out of it at the time he kidnapped Sinatra that he didn't even consider it a crime, since he planned to invest the ransom money and pay back every cent to the family.
Arrested by the FBI soon after the crime, Keenan's long prison sentence was cut short due to him being declared legally insane at the time of the kidnapping. Keenan ended up only serving five years before his release, after which he made and lost a $17 million fortune, became sober, and involved himself in the cause of criminal justice reform. Quite the colorful story.
Read about the lives of nine other infamous criminals here.