care, protection from violence and economic security. For many women, those promises didn’t hold true and they turned to addiction or died by suicide. In contrast, we remember Olive as Billings’ most successful madam and one of its most flamboyant citizens.
OPEN SECRETS Olive didn’t stay long in Etta Feeley’s employ. By 1902, city records reveal eight women lived in a Montana Avenue “boarding house” that Olive owned. “Boarding house” was a euphemism for brothel. That same year, Olive sued Mrs. Jack Little over the wrongful cancellation of a lease, back rent and property damages at another property she owned. The judgment against Mrs. Little exceeded $7,000 in 2020 dollars. Vociferous Billings residents complained that prostitution activity was too close to Montana Avenue’s railroad depot, resulting in Olive and others being told to move off Montana Avenue or leave town. Olive relocated across the tracks and one block south, constructing a building at 2512 Minnesota Ave. No doubt financed by the prominent Billings lawyer who lavished extravagant jewelry upon her, the new establishment became the “Lucky Diamond.” Montana’s finest brothel, it boasted a working telephone, velvet draperies, mahogany furnishings, beautiful women and a discreet back stairway. Olive caused quite a stir when, bedecked in her plumed hat and velvet riding attire, she rode her elegant black horse side saddle through residential neighborhoods. Local society was set on its ear when, upon the death of her prominent lawyer, she sent a large horseshoe-shaped wreath covered with red roses to his NOVEMBER/DECEMBER 2020
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