Manhattan Madam Kristin Davis (not to be confused with Sex and the City co-star of the same name) oversaw three prostitution rings: Wicked Models, New York Body Miracle and Maison de L’Amour. She earned millions servicing high-end clients who paid no less than $1,000 per hour. A former girlfriend of baseball star Alex “A-Rod” Rodriguez, she spent four months on Rikers Island and has considered politics as a new career. Please note, she always paid her taxes on time.