There were houses of prostitution, including most famously Madam Lou Harper's "Mansion" at 219 West Monroe Street (today; 228 West Monroe Street) between Wells and Franklin, and Francis Warren's troupe of streetwalkers, who resided between Clark and LaSalle.
By 1858, Plant had built "Roger's Barracks," a set of poorly-constructed shacks centered on the northeast corner of 5th Avenue (Wells Street) and Monroe. The Barracks, later known as "Under the Willow" (1858-1868), so named after a single sad willow tree which stood on the corner, was the center for all vice in the city up through the end of the Civil War (1861-1865). It was Plant who popularized the catchphrase ─ "Why Not?" ─ which was emblazoned on each of the blue window shades in the complex.
Plant himself was diminutive, at just over five feet tall and no more than 100 lbs, but he was apparently a vicious fighter, skillful with a pistol, knife, and club, but especially with his fists and teeth. The only one who could ever whip him, it is said, was Mrs. Plant, a mountainous woman weighing at least 250 lbs. Plant kept order in the saloon on the premises, and operated as a fence and a bail bondsman, while his wife ran a brothel with no fewer than 80 girls, they rented out cubbies on the property for use by streetwalkers and made a trade of "white slave girls."
Some of the permanent residents of the Plant complex included Mary Hodges, an apparently fantastically talented shoplifter, who it is said, in tall-tale fashion, would drive a cart into the shopping district several times a week to bring back her takings. Another was Mary Brennan ("an audacious old sinner", says the Tribune), who was herself a thief, but also the trainer of thieves and pickpockets. Mrs. Brennan's two daughters were caught breaking into a home whose owner was away on business one afternoon in 1866, and as punishment, were placed in the St. Aloysius Catholic Asylum on Prairie Avenue, separated from their mother until adulthood.
Another long-time tenant was Lib Woods. Miss Woods arrived in Chicago in 1855 and was described in 1860 as "one of the gayest, prettiest, most fascinating creatures that could be found among her class in this city…. with a splendid head of hair that made her rivals all despair. It hung down below her waist, in long, glassy ringlets."
Conley's Patch was leveled in the Great Chicago Fire in 1871.
Compiled by Neil Gale, Ph.D.