“Chicago Joe” and Her Reign in Helena, Montana

During her relatively short life, she was known by multiple names:  Mary Welch, Josephine Airey,  “Chicago Joe,” Mrs. James Hensley, and the “Richest Woman in Helena. Montana.”  She perhaps is best remembered today for her career as a saloonkeeper and brothel madam of the Old West.

She was born about 1844 as Mary Welch, a fairly common surname in Protestant Northern Ireland.  Evidence indicates that the family was Catholic, which may have contributed to their decision to emigrate to America in 1858 when she was 14 years old.  The family landed in New York and apparently determined to stay there.  Her parents doted on the girl, making sure of her education, including attendance at a “etiquette school.”  As Mary grew to maturity in “The Big Apple,” the Irish lass determined to change her name and settled on Josephine Airey, a surname with Scottish origins.  

As Josephine, she soon tired of New York and looked west to Chicago as a likely place to seek her fortune.  In Chicago, where she would be no embarrassment to her family, she gravitated to prostitution.  Although she would carry the nickname “Chicago Joe” for the rest of her life, Josephine’s stay in the Windy City was relatively short.  Still restless and scouting for quick riches, she was attracted to Helena, Montana, founded as a gold camp and established as a city in 1864. Three years later Josephine arrived and immediately went to work.  She had come to the right place.  As a result of the gold rush, Helena rapidly was becoming a wealthy city.  By 1888 an estimated 50 millionaires resided there. 

Helena MT in late 1880s

 

Josephine knew exactly what the miners needed.  At the age of 23 she opened a brothel in Helena in a log cabin.  Despite the primitive surroundings, she employed a small orchestra to provide additional entertainment for the male patrons.  Noted one observer:  “Josephine’s brothel took off in terms of popularity.”   Before long she moved to larger, more elegant quarters. 

In May 1884, Chicago Joe’s establishment was challenged when a passenger on a train stopping in Helena headed straight to the local police.  He reported that seven girls who had come into town on the same train with him had been lured to Montana from the East by Josephine on the promise of work in a local hotel. Their true destination, he claimed, was dancing and selling drinks in her bawdy house.  As reported in the Helena Daily Independent:  “The report soon gained pretty general circulation and a good deal of interest in this affair was shown.”  The mayor sent two officers to investigate.  Upon returning from Josephine’s establishment the men reported that in Chicago when the girls boarded the train — a trip paid for by Josephine — they knew “what service would be expected of them.”

Still skeptical, the newspaper sent a reporter to investigate further.  “The reporter rang the doorbell of Chicago Joe’s residence and the summons was answered by the proprietess herself.”  She gathered the seven women, all of whom attested that before embarking to Helena they fully comprehended the work they were to do.  “This of course settled the matter, and the reporter withdrew.”   The women clearly had found themselves more affluent than they had ever been as they shared in the profits of drinks sold, dancing with customers and “personal services.”  The prospect of meeting and marrying one of Helena’s millionaires was further incentive.

The reporter might have inquired but apparently did not about an incident that had occurred at Josephine’s several days earlier.  A longtime employee, a “dancer” named Martha Hughes, better known as “Dutch Leina,” was found dead on the premises, seemingly from the effects of morphine, self-administered.  “An empty envelope marked “15 grains “ morphine was found in the room…It is supposed that the the diseased took it all at one dose.” reported the Daily Independent.  A coroner’s jury ruled Dutch Leina’s death a suicide.  No motive was given for her act other than she had been drinking heavily on that day and had to be put to bed.

No amount of controversy seemed to impede Josephine’s upward trajectory in Helena.  When a fire in 1874 damaged buildings owned by residents who lacked the resource to rebuild, she bought up the properties, refurbishing them and renting out the space.  A shrewd business woman, Josephine is said to have mortgaged each property, including “three dozen pair of underclothes.”  As a result, she became one of the largest—and richest— landowners in Helena.  By this time she also opened the largest brothel in town, shown here, located at the corner of State and Joliet Streets.  Josephine called it the “Grand,” a building that stood until torn down in the 1970s.

Possibly because her real estate dealings brought her into frequent contact with the businessmen of Helena, Josephine decided to marry and have a man around able to assist her.  She met James T. Hensley, decided he was a likely prospect and wed him in 1878.  Hensley may not have been her first husband, it turns out.  I have found a document indicating that under the name “Mary Welch” she was recorded marrying an Albert Jenkins in Montana in April 1869.  After that nothing more is heard of Jenkins.

With Hensley as a partner, Josephine continued her ascent in Helena.  With her husband’s help she built and opened the Red Light Saloon and a large variety theatre, costing $30,000 to construct.  (That is equivalent to just short of $1 million today.)  The couple called it “The Coliseum.”  The venue was a success with its fancy furnishings, beautiful girls who performed — and an adjoining brothel.

Josephine became known for her elegant dress, fancy lifestyle and the elegant parties she and Hensley threw.  Shown here is an open invitation from Josephine for a “masked ball” on Christmas Eve 1883 at the Red Light Saloon.  As shown here, at such occasions Josephine would appear in all her finery.  Wearing diamond rings on her fingers, elegant earrings, a large necklace, and a fancy tiara, she had every inch of a regal bearing.  The madam known as “Chicago Joe” had become the “Queen of the Red Light District.” She also gained a reputation for her generous donations to local charities and political candidates.

Her example set a business model for other Montana women, including her former “girls.”  In 1875 Lou Couselle, after a stint with Josephine, opened her own brothel in Bozeman, Montana.  She also used mortgages and the profits of prostitution to her advantage.  At the time of her death Lou had an estate of $20,000 (current value $616,000).  “Mollie "Crazy Belle” Crafton was another woman in Helena reputed to have followed the path blazed by Josephine:  “Mollie built the Castle Bordello, which cost over $12,000 in the early 1880s. Josephine's success clearly had a profound effect on the minds of other women in the area at this time,”  recorded one observer.

Power and popularity, however, could be fleeting in the Old West.  As an absentee owner, Josephine was vulnerable to theft of her horses and cattle.  An incident occurred in April 1882 when John Miles, alias Bronco Johnny, with an accomplice, raided her ranch in nearby Silver Creek.  Although forewarned, lawmen waiting in ambush caught the sidekick.  Johnny got away with a stolen horse, at least temporarily.

Josephine also faced legal problems.  In 1885 the Montana legislature instituted a ban on brothels, key to her business empire.  Many such houses in the state were forced to shut down.  When she did not, authorities took her to court.  Able to afford the best legal talent in Montana, her lawyer ensured she was found innocent.  He pointed out to the court that the law plainly stated that the brothels to be shut down were “hurdy gurdy” joints, where music was provided by turning a crank on a box.  He was able to demonstrate that Josephine had never used that method of entertaining.  Nonetheless, for a time afterward, she closed her houses, quietly opening a new one later as adjunct to her “Variety Theater.”

Apparently reluctant to leave him, Josephine was also having difficulty with husband Hensley.  He was drinking heavily and, often when drunk, gambled away her money. In January 1883 she placed a notice, seen above, in the Daily Independent notifying liquor dealers in Helena not to sell Hensley intoxicants, gambling houses not to let him play, and for no one to lend him money.  “Any one that does contrary to this notice I will prosecute.”  She signed the notice:  “Mrs. Josephine Hensley.” 

A crushing financial blow for came for Chicago Joe with the Financial Panic of 1893.  Apparently caused by a series of negative worldwide economic developments, including a stock crash on Wall Street, the ripple effect reached Helena where Josephine found herself highly leveraged and her creditors demanding immediate payment.  She watched as one by one her large property holdings were gobbled up by others.  Left virtually penniless, except for the Red Light Saloon, she and Hensley were forced to live in small rooms above the drinking establishment they had built.

In October 1899 Josephine was struck down by pneumonia at the age of about 55.  The glory of her early days in Helena was gone.  Nonetheless her death saddened many who had come to know her and made front-page news in the Daily Independent.  Her obituary there emphasized her generosity and charitable giving.  Following rites of the Catholic Church, Josephine was buried in St. Mary’s Cemetery in Helena.  She is remembered today in Helena’s Montana Historical Society Museum where her ornate make-up box, below, is on display. 

Notes:  Josephine’s story is told in several sites on the Internet as well as articles in the Helena Daily Independent, that consistently referred to her as “Chicago Joe.”  Wikipedia also contains information and photographs of this enterprising woman of the rowdy Old West.