Chicago Joe – Queen of Helena, Montana

Josephine Hensley, colorized

Josephine Hensley, better known as Chicago Joe

Josephine Hensley, better known as Chicago Joe, was one of the best-known people in Helena, Montana, during its “Eldorado” heydays.

Born in Ireland as Mary Welch in 1844, she emigrated to New York in 1858 and changed her name to Josephine Airery. Her hard-working and loving parents 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 a train, landing in Chicago, Illinois. Out of money, she found herself in the role of a “working girl.” 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 23, 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 several new girls from Chicago, who also found themselves successful as they shared in the profits of their personal services and the profits of drinks sold and dancing with the customers.

The "Grand" bordello, Helena, Montana

During Helena’s booming mine days, Chicago Joe owned the “Grand” bordello at State and Joliet Streets.  The building was torn down in the 1970s. Photo, 1942  by John Vachon.

By 1874, Hensley was doing so well that she moved her business into a larger building and began to invest in real estate, forming several partnerships with the town’s affluent businessmen. She married James T. Hensley in 1878, and together they built a dance hall and the “Red Light Saloon.” 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 and having her hand in several 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.

Helena, Montana 1883.

Helena, Montana 1883.

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 held on to her main establishment, which continued to operate until she died in 1899. At the age of 56, Josephine succumbed to pneumonia. Her funeral was a splendid affair attended by several of Helena’s leading citizens.

© Kathy Weiser/Legends of America, updated May 2023.  Credits & Resources

Also See:

Complete List of Female Pioneers, Heroines, Outlaws & More

Heroines in the Rocky Mountains

Leading Madams of the Old West

Painted Ladies of the Old West

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