Weird History

11 Infamous Outlaws Who Wound Up Working For The Man In The End  

Melissa Sartore
20.5k views 11 items

Numerous outlaws throughout history came back around from their rabble-rousing and trouble-causing days to serve as lawmen, government leaders, and agents of criminal-catching agencies. From the Middle Ages to the Wild West to the Information Age, historical and geographical boundaries need not apply when it comes to outlawry. Some outlaws – mostly men but not always – are famous, but others are obscure historical figures. Their motivations on both sides of the legal fence varied, as did their successes when it came to breaking, making, or working with the law. Whether they were traitors, sell outs, or simply switched to the other side, messing with any of these outlaws was never a very good idea regardless of where they stood on a particular day.

Pancho Villa is listed (or ranked) 1 on the list 11 Infamous Outlaws Who Wound Up Working For The Man In The End
Photo:  Bain News Service/Wikimedia Commons/CC BY-SA 3.0

Francisco “Pancho” Villa was born Doroteo Arango in 1878, and he became a bandit at the age of 16 after shooting the man that allegedly raped his younger sister. Doroteo fled to the mountains but was soon arrested and forced to join the Mexican Army. He deserted shortly thereafter and became a cattle-rustler in the state of Chihuahua, where he took the name Francisco Villa. In 1909, Pancho Villa joined Francisco Madero’s rebellion against Mexican Dictator Porfirio-Diaz and waged numerous successful battles on behalf of the common people; this led to his position of Governor of the state of Chihuahua in 1913. 

Villa repeatedly engaged in guerilla-style campaigns, including one against troops from the United States, which was funded in large part through his gubernatorial revenue streams. Villa printed his own currency, parceled out land, recruited for the military, and acquired a vast amount of wealth that he distributed to the people of Mexico – all while not being recognized as the legitimate leader of the country. Villa continued fighting until 1920 when all of his rivals were eliminated. He then negotiated a pardon, received a government pension, and lived out his days on a land settlement in the state of Chihuahua until his assassination in 1923.

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Wayne 'Big Chuck' Bradsh... is listed (or ranked) 2 on the list 11 Infamous Outlaws Who Wound Up Working For The Man In The End
Photo: Neil. Moralee/flickr/CC-BY-NC-ND 2.0
Wayne 'Big Chuck' Bradshaw, Motorcycle Outlaw Turned Narc

In the late 1970s, Wayne “Big Chuck” Bradshaw went from being a member of the outlaw motorcycle club, the Pagans, in New Jersey to an undercover narcotics officer for the New Jersey police. After a bar fight in 1977 amongst rival biker gangs in which Bradshaw punched, slashed, and wrestled his way to victory over five bleeding rival bikers, Bradshaw realized how grim the event was and that the fighting wasn’t in him anymore. He went to work for the police instead, going back to the same places where he was once the troublemaker, only on the other side of the law.

Nelson Mandela is listed (or ranked) 3 on the list 11 Infamous Outlaws Who Wound Up Working For The Man In The End
Photo: bigskyred/flickr/CC-BY-NC 2.0

Nelson Mandela became the first democratic leader of South Africa in 1990 after a long career of protest, controversy, and confinement. Born in 1918, Mandela spent his youth studying law and opposing South African Apartheid. He joined the African National Congress (ANC) in 1944, and, as the ANC became more radical in their efforts against Apartheid, Mandela led the militant wing of the party. Mandela was arrested and put on trial for his actions in 1952, served nine months of hard labor, and was released that same year. He continued protests and acts of defiance, getting arrested again in 1955 and forced to go underground as a fugitive in 1960. 

In January 1962, Mandela left South Africa under a fake name. He traveled to Britain and throughout Africa to acquire military training and gather support for the ANC cause. He was arrested shortly after his return to South Africa during the summer of 1962. Upon his return, he stood trial for several offenses, including leaving the country, inciting strikes, and sabotage.  He was sentenced to life at the remote prison on Robben Island in June 1964. After his release in 1988, Mandela reentered politics. He was elected President of South Africa in the 1990s and, after one term, stepped down to found and lead numerous charitable organizations.

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Phoolan Devi is listed (or ranked) 4 on the list 11 Infamous Outlaws Who Wound Up Working For The Man In The End
Photo: txmx 2/flickr/CC-BY-NC-ND 2.0

Phoolan Devi was born in India in 1930 to a low-caste family. She was sold into marriage at 10 years of age but was returned by her abusive husband after a year. Phoolan then took up with various men – a thing considered shameful by other women – and was arrested in a land dispute in 1979. In prison, she was raped, and upon her release, she was captured by a band of dacoits, or Indian bandits. The leader of the gang abused Phoolan until he was killed by another member, Vickram Mallah. Mallah became the head of the gang, and soon Phoolan was his gang-wife. Vickram, Phoolan, and the gang of bandits abducted, murdered, and robbed throughout India during the late 1970s, and, after Vickram was killed in 1980, Phoolan left the gang and formed another with her new boyfriend. On Valentine’s Day 1981, Phoolan and the gang retaliated against Vickram’s death by killing 22 high-cast young men from the village that once was home to his killer. 

On the run until February 1983, Phoolan and her gang then surrendered to authorities, and she was imprisoned for 11 years. When Phoolan was released, she entered Indian politics and was elected to the lower house of Parliament in 1996. Phoolan was assassinated in 2001.