10 Infamous (Non-State) Criminals
It has been said that crime doesn’t pay, although presumably criminals disagree. Throughout history, many have decided not to play by the rules and either won big or lost heavily. But what happened to history’s most notorious men and women after their lawbreaking days were over?
10 The Kidnapper Of Frank Sinatra Jr. Is A Wealthy Businessman
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On December 8, 1963, Frank Sinatra Jr., the 19-year-old son of legendary entertainer Frank Sinatra, was performing in a hotel in Lake Tahoe, Nevada. That night, a knock on his dressing room door introduced him to demented gunman Barry Keenan, who proceeded to kidnap him and demand a $240,000 ransom. (Frank Sinatra Sr. actually offered $1 million, but Keenan insisted on $240,000.)
Born in 1940, Barry Keenan grew up to a life of privilege. In fact, he was a friend of Nancy Sinatra and had met Frank Sr. on several occasions. A rising star in the business world, Keenan became the youngest member of the Los Angeles Stock Exchange at just 21. However, a 1961 car accident left Keenan debilitated and addicted to the painkiller Percodan. Penniless, alcoholic, and drug-addled, Keenan decided to perform his most lucrative business deal of his life—”borrowing” Frank Sinatra Jr. At the time, Keenan didn’t consider the kidnapping a crime, since he planned to invest the ransom and then pay it back with interest.
Naturally, his plan didn’t quite work out and the FBI soon arrested him and his accomplices. Keenan initially received a hefty sentence but served less than five years due to being judged legally insane at the time of the crime. During his trial, Keenan falsely suggested Sinatra Jr. had organized his own kidnapping as a publicity stunt, a lie that he now calls his “biggest regret.”
After his release, Keenan returned to business and became a real estate developer. After making and losing a $17 million fortune, Keenan successfully quit drinking and using drugs. He now runs several charities to help addicts achieve sobriety, and his business interests have once again made him a wealthy man. He is also an advocate for criminal justice reform, arguing that while he had wealthy friends to help him get back on his feet, many inmates “come out of prison with nothing but $50, a bus ticket, and the clothes on their back. What chance do they have of going straight? What do you think they’re gonna do when that $50 is gone?”
9 New York Madam Polly Adler Wrote A Memoir
While living on the seedier side of New York City, Russian immigrant Polly Adler met a bootlegger who paid to use her apartment for some personal time with his girlfriend. From such humble beginnings an empire was born. Soon, Adler was running New York’s most famous bordello, where gangsters like Lucky Luciano and Dutch Schulz mixed with businessmen and even Mayor Jimmy Walker. Dorothy Parker was known to drop by for a drink and columnist Robert Benchley would always check in when he had a deadline to meet, telling Adler that the service there was better than the Waldorf. It’s been suggested that Judge Joseph Crater, who famously went missing in 1930, might have had a heart attack while with one of Adler’s girls, forcing her to dispose of the body to avoid a scandal.
When the Seabury Commission was set up to investigate corruption in New York, Adler went on the run for six months but was found and forced to testify in 1931. Although she avoided a conviction, several of her police contacts were jailed for taking bribes. Ironically, this actually made Adler’s life easier, since she no longer had to split her profits with law enforcement. Business flourished until 1936, when Fiorello LaGuardia was elected mayor on a promise to clean up the city. Adler was soon arrested for the 16th time and sentenced to 30 days in prison for “maintaining a disreputable apartment.”
After her release, Adler was determined to move to a more legitimate life but found that her past followed her everywhere. A nightclub owner said that she was the perfect businesswoman, but the police actively dissuaded anyone from doing business with her. With her financial situation worsening, Adler attempted to work as a cigarette girl, but nobody would agree to hire her. She returned to being a madam until 1943, when she finally saved enough money to retire and move to Burbank, California. There, she wrote a memoir called A House Is Not A Home, which was made into a film in 1964. Shortly before her death in 1962, Adler successfully completed her proudest achievement: finishing high school.
8 The Great Train Robbery Mastermind Escaped And Lived Quietly
On August 8, 1963, 15 men looted a Royal Mail train of £2.6 million (roughly £48 million in today’s money), severely injuring a worker named Jack Mills in the process. The “Great Train Robbery” quickly became one of the most infamous crimes in British history, and while the robbers themselves were apprehended, the majority of the money was never recovered. A portion of it went to the crime’s mastermind, a shadowy figure known only as “the Ulsterman” due to his strong Northern Irish accent. For the next 50 years, the authorities were mystified as to the identify of this key figure.
In 2014, train robber Gordon Goody finally revealed that the “Ulsterman” was a mild-mannered postal worker named Patrick McKenna. While McKenna never actually revealed his identity to the gang, he once dropped his glasses case while buying ice cream, allowing Goody to see the name written inside. McKenna was apparently furious, but Goody promised he would never say a word. But since McKenna was clearly middle-aged in 1963, Goody decided that there was no harm in opening up half a century later, when the “Ulsterman” would almost certainly be dead.
With Goody’s help, a documentary crew was able to track down a Patrick McKenna who worked for the Royal Mail, giving him access to the inside information needed to plan the job. Apparently, the mastermind never committed another heist (as far as we know) and continued to live quietly until his death in 1992. Oddly, while his share of the money would be worth around £2.5 million today, McKenna never lived any better than before. In fact, McKenna died with just £3,000 in his bank account, prompting speculation about just what happened to the money. Goody thinks McKenna’s share might have been stolen by one of the other robbers, while others have speculated that he might have donated it to the Catholic Church over the years.
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