One of the best known people in Helena, Montana during its "Eldorado” heydays was Chicago Joe. Though born as Josephine Hensley on June 1, 1846, she was better known to Josie to her family and friends. Her hard working and loving parents, immigrants from Italy, provided her with every need, sending her first to regular school in New York, then to etiquette school.

But, it was not enough for the adventurous girl. When she turned 18, she headed westward on the train. However, she was ill-prepared and by the time she arrived in a small town in Iowa, she was already out of money. Destitute, she found herself in the role of a "working girl.”  But, this seemingly didn’t perturb her and with money in her pocket, she soon headed out again, landing in Chicago, and setting up a new "shop.”

Josephine Hensley was better known as "Chicago Joe"  to her Helena, Montana admirers.

This image is available for photographic prints HERE!

However, when gold was discovered in Montana and word reached Chicago of the booming mining camp of Helena, Hensley decided to take advantage of the "business opportunities” that a prosperous mining camp could provide.

At the age of twenty-three, the perky, curly-haired girl established Helena’s first house of ill-repute in a log cabin. Providing a full orchestra as additional entertainment for her customers, Henley’s business was an immediate success among her customers, who soon dubbed her "Chicago Joe.”

The popular madam soon recruited a number of new girls from Chicago, who also found themselves successful as the shared in not only the profits of their personal services, but also in the profits of drinks sold and dancing with the customers.

By 1874, Hensley was doing so well that she moved her business into a larger building and began to invest in real estate, forming a number of partnerships with the town’s affluent businessmen. She soon was the largest landowner in the red light district which flourished between Wood and Bridge Streets, owning the "Grand” bordello, the Red Light Saloon, and the Coliseum variety theater, as well as having her hand in a number of other businesses.

But, prosperity for Chicago Joe would not continue at the same pace. In 1885, the Montana legislature ordered the prohibition of "hurdy-gurdy” houses. As the "Queen of the Red Light District,” the new law sought to prosecute Josephine first. However, when she was hauled into court, her attorney pointed out that she didn’t and never had provided musical entertainment by means of a "hurdy-gurdy.” She was found not guilty. Montana's attempt to "lump” all such businesses into the catch-all term of "hurdy-gurdy” had failed.

However, the writing was on the wall for the thriving red light district. Josephine closed up "shop” for a while and kept a low profile. Later, she reopened her business, hiding behind the façade of a "variety theater,” where personal services could also be obtained.

The nationwide Panic of 1893 took its toll on Hensley and she found herself financially overextended. However, she was able to hold on to her main establishment which continued to operate until her death in 1899. At the age of 56, Josephine succumbed to pneumonia. Her funeral was a splendid affair that was attended by a number of Helena’s leading citizens.

© Kathy Weiser/Legends of America, updated January 2013