Bozeman historian B. Derek Strahn, writing for the website "Distictly Montana", gives us the lowdown on Chicago Joe and two other successful Helena prostutute/madams:

Mirroring Helena’s prosperous aura was its extensive red light district, which flourished between Wood and Bridge Streets. Initially, a number of “proprietor prostitutes” working alone out of small houses that they owned, defined the district. By the 1880s, however, a few increasingly powerful madams consolidated ownership of the tenderloin, erecting several large parlors and colorful bawdy houses. By 1886, no less than 52 white prostitutes worked in Helena’s demimonde, which for more than 20 years had constituted the town’s largest single source of women’s employment outside of the home.

One of the most prominent madams in Helena during this time was Josephine Airey “Chicago Joe” Hensley who, beginning in 1871, shrewdly manipulated a series of business deals to become “the queen of the city’s red light district.” Mortgaging everything, including “three dozen pair of underclothes,” she rapidly became the largest landowner on Wood Street. At the peak of her success, “Chicago Joe” had invested more than $30,000 to erect the Coliseum, a vaudevillian variety theater, and other sizable building projects. But the nationwide Panic of 1893 found her financially overextended, and virtually all of her property ultimately transferred to others. She died of pneumonia a few years later at the age of 56.

Mollie “Crazy Belle Crafton” Byrnes was another significant player in Helena’s red light distirct. Born in New Orleans, Byrnes settled in Helena in 1881 and set up operations in the heart of the demimonde. By May of 1884, she secured the old Kiyus Saloon property, while renting several other residential properties in other parts of the city. Two years later she financed the construction of a grand, $12,000 bordello that soon became known as “the castle.” By 1899, Byrnes sold her flagship property to a local hotel owner. When she died of acute alcoholism a year later, her estate was valued at $20,000 cash in real and personal property.

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Another successful Helena prostitute was Louisa Couselle who, like Hensley and Byrnes, regularly bought and sold property while extending mortgages to others. Sensing opportunity in uncharted waters, Couselle soon relocated to Bozeman, where competition was virtually non-existent. With impressive financial resources at her disposal, Couselle purchased a total of 15 lots, laying the foundation for a rapidly-growing tenderloin that would flourish one half block north of Main Street between North Rouse and North Bozeman Avenues. The enterprise was very profitable, and by 1878, Couselle was of greater economic means than roughly 95 percent of Bozeman’s citizens. Her stature was so impressive that The Avant Courier Annual Almanac listed her as one of the 59 “heavy taxpayers of Gallatin County.

From the Helena Independent, Nov. 18, 1935: The courthouse clock is no more. The "highboy" of Helena which lifted its sad face to the four winds, each telling a different story of the time, is to be permanently done away with.

After fifty years of faithful service, during which time at least one face always told the correct time, the old clock gave up the battle and fell a prey to the earthquake bugaboo. It was ordered removed along with all the heavy chimneys and fancy brownstone work which constituted hazards to the building and the public.

When the courthouse building was erected in 1885, the crowning touch of glory to the massive stone structure, was the tower and clock on the north face of the building over the front door. Because of the manner in which the building was situated in its full block of grass, flower beds and walks and the near proximity of Broadway to the rear, the front door was often regarded as the back and the back door as the front and the side door on the east, through which prisoners were brought from the courtroom to the jail, as the door of sorrow.

Saturday morning the south face of the clock, which lifted up its hands to the noonday sun and asked for prompt payment of all tax obligations, was taken down by workmen who tenderly removed it from the tower and consigned it to the land of forgotten things. And so today the face on the north which says 6:15 and the face on the east which says 8:32 and the face on the west which says nothing, will be retired from public life.

This photo shows the Presbyterian Church (1875-1890) at the corner of 5th and Ewing; this area is currently the County Courthouse parking lot. In the background we see the just-
completed courthouse and jail. This photo must have been taken from roof of the Chessman apts., in 1889 or 1890.

Just over the right edge of the courthouse roof is the steeple of the old Methodist Church on Broadway.