As filmmaker Robin Hamilton did research for her documentary on the life of Odessa Madre — the so-called queen of Washington’s underworld — she couldn’t help but wonder: What if?

“She was brilliant,” Hamilton said of Madre. “She won oratory contests. She was brilliant with numbers. You can’t help but wonder, if things had been different, who she could have been.”

Who Madre was is the subject of “Odessa’s Reign,” Hamilton’s half-hour documentary, which airs several times this month on WHUT-TV.

Hamilton’s interest was piqued after seeing a historical marker in the District describing Madre as the Al Capone of Washington.

Said Hamilton: “I thought what? Who is this woman? What was her deal?”

Odessa Marie Madre was born in 1907. She grew up in “Cowtown,” around Georgia and Florida avenues NW, named because it was where livestock were allowed to roam. She went to Dunbar, an elite public school that many considered as rigorous as any college. It was not a pleasant experience.

“For a lot of African Americans, it was understood that if you didn’t look a certain way, you were not allowed to be upwardly mobile, economically or socially,” Hamilton said.

The dark-skinned Madre was taunted cruelly by lighter-skinned students.

“There was only three Blacks at Dunbar back then — I mean Black like me,” she told Courtland Milloy for a remarkable 1980 profile in The Washington Post. “I had good diction, I knew the gestures, but they always made fun of me.”

Shunned by her classmates, Madre embraced a different crowd. She turned her skills toward bootlegging and numbers-running, becoming as formidable an underworld figure as her occasional collaborator Roger “Whitetop” Simkins.

“Odessa was tight with a number of policemen,” Hamilton said. “She had grown up in Cowtown, where a lot of Irish cops had grown up. It was understood she would provide the ‘ice’ ” — bribes — “and they would be loyal to her.”

The protection allowed Madre to flourish, buying expensive cars and furs, distributing largesse in the community, and never hiding her bisexuality.

“She was unapologetic about who she was, not only as a woman, but as a lesbian and as someone who wanted to be a power broker in the underworld,” Hamilton said.

Madre ran a brothel, too, and was known for providing customers with fairer-skinned Black prostitutes.

“I don’t want to say it was revenge, but it was very ironic that the very women who would shun her were the same women she employed,” Hamilton said.

Among the people interviewed for the film were Sharon Harley, a University of Maryland professor who has written about Madre, and Rohulamin Quander, a retired D.C. administrative judge whose uncle was involved in the numbers game.

Others weren’t quite so eager to share what they knew about the numbers queen.

“I’ve never had so many people reluctant to talk,” Hamilton said. “There are definitely some older Black folks who know about her and do not want to talk about her.”

Madre died in 1990 at the age of 82. She was near-destitute — ill-gotten gains are hard to invest — and had spent time in prison.

After her funeral, The Post’s Milloy caught up with retired D.C. police officer Miller A. Dixon, who had crossed paths with her often.

“I had a lot of respect for Odessa,” Dixon said. “She was the only person I ever met who had just made the decision early on to be bad. She said, ‘To hell with it,’ and went on about her business.”

Hamilton lives in Capitol Heights. Some of her earlier documentaries focus on more conventional heroines, such as civil rights figures Mary Church Terrell and Fannie Lou Hamer. Why do we also seem drawn to outlaw figures such as Odessa Madre?

“I do not celebrate crime at all,” Hamilton said. “But there is a part of me that thinks, wow, here you have this woman who said, ‘I really don’t care. I’m going to do this my way. This is the way I’m going to get that wealth that I want. And I’m going to do it on my own terms.’ ”

Said Hamilton: “It’s that level of confidence and flouting of rules and of a system that would never really accept her anyway. She said, ‘You know what? You didn’t want me. I’m going to find a place in this world where I’m doing what I want.’ ”

“Odessa’s Reign” was made with funding help from Humanities D.C.

It is scheduled to air on WHUT-TV on Wednesday at 8 p.m.; Thursday at midnight; Saturday at 8:30 p.m.; Sunday at 12:30 a.m. and 6:30 p.m.; and Oct. 28 at 11:30 p.m.

Twitter: @johnkelly

For previous columns, visit washingtonpost.com/john-kelly.