Odessa Madre grew up in a section of Washington DC called Cowtown, because farm animals would occasionally wander its streets. Born in 1907 in abject poverty, she nonetheless lived and thrived in a deeply segregated city as a dark-skinned African-American woman. “There was only three Blacks at Dunbar (High School) back then — I mean Black like me,” she later recalled. “I had good diction, I knew the gestures, but they still made fun of me.” Dess, as many called her, was also a lesbian, and not too shy about it. “I just couldn’t keep no watchamacallit — a man. I guess I was just born to give orders not take them. What kind of man wants a woman like that?”

She went on to become one of the wealthiest African Americans in an overwhelmingly black city — hauling in over $100,000 a year at her peak — by becoming “the female Al Capone.” She ran brothels, pimped women, owned speakeasies, as well as owning a legit and legendary institution on 14th Street, Club Madre. Jamie Kirchick conjures up a scene from the 1940s:

The crowd roared its approval whenever Madre, covered in mink furs and diamonds and trailed by a multiracial retinue of women for sale, entered the premises and sauntered over to the central table, denoted as hers by an ever-present vase holding a dozen long-stemmed roses.

Among the performers at the club: Billie Holiday, Duke Ellington and Count Basie. Madre kept all her illicit businesses alive by the old-fashioned method of bribing the fathomlessly corrupt DC police — “You know I practically ran that damn police department,” she later quipped — and became a renowned mediator of mob disputes across the country.

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