Miss Ollie Brackett’s Secret

The most famous prostitute of Punta Gorda was Miss Ollie Brackett. Ollie ran a “disorderly, bawdy house of ill repute” at the west end of Marion Avenue – in those days it was known as the bad part of town. Miss Ollie served a few very select customers herself and managed her “stable” of seven “ponies” who handled the majority of the clientele.

Back in the day there were several brothels here in Punta Gorda. It was a rough pioneer town populated with scores of unmarried cattle men, fishermen, railroad workers and tradesmen. Besides the houses with red lights, there were houseboats of girls on call for fishermen located in what was known as Whore Bay.

Her unusual feature

On occasion Miss Ollie would ride into town to take care of business, and such events were highly sensational. She rode sidesaddle on a big white horse, scandalously attired in a provocative dress, a hat with a plume, and her long red hair loose. She was the quintessential madam, except for one distinguishing feature. Miss Ollie was at least 6 feet tall, which inspired her nickname, Big Six.

Miss Ollie falls ill

On December 5, 1894 Miss Ollie fell very ill with dysentery. Her girls wanted to call a doctor, but Ollie wouldn’t allow it. No matter how much they pleaded, she refused to let them get the doctor. In time, she fell into a coma. That’s when the girls got the doctor.

Her secret revealed

As the doctor examined her, he discovered something startling, and called for three witnesses to attend Miss Ollie’s deathbed. Miss Ollie Brackett was a man! Before taking her last breath she told those in attendance a few details of her lurid life.

Witnesses opened a trunk in her home and discovered a marriage certificate in the name of Maria Dempsey to William Patrick on March 2, 1892 in Hillsborough County.

Marriage license of William Patrick and Maria Dempsey aka Big Six.

Big Six’s true name was George Asbell. He fled Alabama after pushing his cousin Tom off a cliff. Moving to Florida, he disguised his identity by dressing as a woman. He found employment as a children’s companion but when the children’s father caught her sneaking out of the house at night to party in town, she was quietly let go. That’s when she got married.

Montgomery Advertiser, AL. December 7, 1894

She left Mr. Patrick a few days into their marriage, after spending all of his money on new dresses. From there she moved to Arcadia where she took up the “wayward life”. Big Six spent time in Jacksonville, Sanford, Palatka and Fort Myers before settling in Punta Gorda. Unfortunately, in those days opioid addiction was a social and health issue much as it is today. It is believed Big Six’s chronic dysentery was caused by her addiction to opium.

Big Six was laid to rest at Indian Spring cemetery in an unmarked grave.

Learn about Punta Gorda’s history!

Hear true stories about Punta Gorda’s history and tragic deaths occurring here on our Haunted History of Punta Gorda Walking Tour.


Our Fascinating Past-Charlotte Harbor: Early Years by Lindsey Williams and U.S. Cleveland; Big Six: A True Story Highly Sensational by J.S. Geiger; Newspapers.com

About Simona Molino

The imagined portrait of Big Six was created by Simona Molino of Janas Studio Artistico in Italy. Janas is a fairy whose magic flights take her to starry skies and silvery seas. She inspires Simona’s fantasy artwork of memorable characters illustrated in rich colors and scrupulous detail.

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