Women Who Broke So Bad They Redefined The Word ‘Criminal’

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Sometimes you have to say f*ck the rules and work outside the system. You can either fail miserably at this, landing yourself some jail time — or you can be good at it, chipping away at morality and virtue as you amass unheard of wealth. It’s the dark side of capitalism: Everybody’s gotta get some. But it’s the lengths to which you’ll go to get some that’s what ends up defining you as a human.

These women, they got some. They got lots. They stepped so far outside the box that they redefined the word “criminal.” In the parlance of our time, they broke bad. Taking a life, ain’t no thing. Running a cartel, easy-peasy. Stopping entire navies, all in a days work. This isn’t about male and females. It’s about predator and prey. Alphas versus betas. The dark side versus the light.

Heidi Fleiss

Designer Heidi Fleiss Poses At Her Home December 15 1993 In Lo

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The Hollywood Madam is — by far — the most innocuous entry on this list. She hasn’t killed anyone. Fleiss started off in prostitution under the famed Madam Alex in 1987. Sensing that most of Alex’s escorts were eyeing retirement, she broke off and started her own prostitution ring. Within four months, she was a millionaire.

Fleiss focused her business on the high end — millionaires, Hollywood elite, and politicians. Her harem consisted exclusively of young and gorgeous escorts. Within a year she was so successful, she was turning away women who wanted to be escorts for her. A legend was born.

And short lived. Fleiss was arrested in 1993. She posted the million-dollar bail without any problem. A court case ensued and she was eventually convicted of tax evasion and sentenced to seven years. She served 20 months. As the ’90s turned into the aughts, she became a C-list celebrity and reality TV personality. She designed some clothes and even tried to open a brothel in Nevada. Today, she raises birds and grows marijuana in her Nevada home.

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