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Olive Warren The Many Secrets of

THE STORY BEHIND ONE OF BILLINGS’ FIRST MADAMS written by VIRGINIA BRYAN photography courtesy WESTERN HERITAGE CENTER

A ROUGH START

Editor’s Note: Over the past century-plus, many women in the

Yellowstone Valley have broken tradition, refusing to let society dictate their path in life. They’ve been comics, political activists, rough-and-tumble history makers and community champions. Earlier this year, under the leadership of Community Historian Lauren Hunley, the Western Heritage Center began honoring 10 of these women with its exhibit “Saints & Sinners: Women Breaking Tradition.” Be sure to catch the exhibit before it closes at the end of 2020. “I am going to chop (you) to pieces!” growled Calamity Jane, hatchet in hand, as she stormed the dry goods aisle of the Yegen Brothers Mercantile on Billings’ Minnesota Avenue in 1902. Some say Calamity was looking for Olive Warren, a 20-something, darkhaired, well-dressed beauty working as a shop clerk that day. A quick-thinking employee intervened, pried the hatchet from Calamity’s hands and escorted her to the front door. If it was Olive Warren, she might have been wearing a particularly large diamond ring, a gift from a prominent Billings lawyer. According to one account, Calamity Jane and the lawyer’s wife chatted over coffee when Calamity delivered wood to the woman’s home. Calamity allegedly recognized the woman's husband as the escort of the beguiling Olive. Was Calamity’s wrath intended for Olive? Was there another motivation? The mystery surrounding the encounter sets the tone for Olive Warren’s colorful, controversial and secretive life in Billings over the next four decades. 84

YVW MAGAZINE

Olive Warren was born in 1873 to Missouri farmers, Jud and Jane Sands Dewey. The Deweys moved their family to Denver in the 1880s. Olive was a teenage bride when she married Thomas Skerritt in 1890. They divorced two years later. A City Directory puts Olive at an address smack dab in the middle of Denver’s red-light district in 1897. By August 1897, she was working at Feeley’s Place, a brothel on Billings’ North Side. Its madam, Edna Feeley, had connections across Wyoming, Denver and Portland. Perhaps she encouraged Olive’s move to Billings, citing less competition and a chance to escape Denver’s depressed economy. Young, uneducated and divorced, Olive had few options. Given her independent streak and business savvy, it's no surprise that she wasn’t content as a cook, laundress, shop clerk or seamstress.

A GROWTH INDUSTRY IN THE AMERICAN WEST Prostitution was a booming business in the West at the onset of the 1900s. Human trafficking was a big problem. By 1910, it was illegal to lure or transport girls and women across state lines or federal boundaries for immoral purposes, prostitution and debauchery. We’re left to wonder if Olive Warren freely chose prostitution, if she was a victim of human trafficking or if she was destitute with no other options. The world’s “oldest profession” enticed women with beautiful clothing, a nice place to live, medical

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Yellowstone Valley Woman  

Yellowstone Valley Woman magazine was started in 2001 as a 40-page free publication in Yellowstone County. Over the years, thanks to your re...

Yellowstone Valley Woman  

Yellowstone Valley Woman magazine was started in 2001 as a 40-page free publication in Yellowstone County. Over the years, thanks to your re...