Longford’s Queen of Crooks | Chicago May, Blackmail Extraordinaire

It was on St Stephens day 1870 when Mary Anne Duignan was born to Thomas Duignan and Mary Elizabeth Brady in Edenmore, Ballinamuck. The eldest of two daughters and three sons, she grew up in comfortable surroundings on a 140 acre farm in the slasher county. Better known by her pet name ‘May’, in later years it was with the name ‘Chicago May’ that she became a notorious criminal and her life of crime began at the age of 19 when she stole her parents life savings and ran away to Liverpool.

When the teen tearaway reached Merseyside in June 1890 she went on a shopping spree. She bought the best fashion and perfume and then booked a first class ticket to take her across the broad Atlantic.

May landed in New York city where she used her good looks and finery to become a prostitute for the city’s better-off gentlemen. Once settled, she crafted the skill of pick pocketing and blackmail. However, while mastering such arts, her family back in Longford had somehow got in touch with her and managed to convince May to head west for Nebraska. There, they suggested she could move in with an uncle and live a respectable life. May agreed to the former. Living a respectable life on the other hand, she simply could not.



Instead of handing over his wealth he put a gun to his head

Working a legal job for meager pay did not seduce May in the same way that crime did and while she was in Nebraska she turned once again to pick pocketing, blackmail and prostitution. She did manage to find a husband in the form of Dal Churchill but he too was gripped with felonious fever.

After Churchill attempted to rob a train, he was caught by angry vigilantes and lynched. May did not mourn for long. His parting gift, her American citizenship through their marriage was positively energising and she decided to go after Chicago next in 1893. At this time the World’s Fair was taking place in the windy city and May sought to capitalise on the influx of visitors there.

May made a name for herself by using photography to blackmail gentlemen who used her services. It was a brazen way to extract money from men who would be known as pillars of society such as judges and politicians. She would hide a photographer in her room and they would snap while the unsuspecting client was in a compromising position. As word spread in Chicago about the blackmailing Irish woman, May headed back to New York.

By the time May reached New York, her exploits in Chicago had already been spread across the gossip lines of the Big Apple. The Longford lass then became known as Chicago May but she preferred another title: Queen of Crooks.

May wasn’t long in New York when she took a second husband, James Montgomery Shape. This young and rich army officer fell under the spell of the buxom auburn haired May but just three months after saying “I do”, the couple divorced and May took 10,000 dollars of Shapes fortune.

Leading a somewhat teflon criminal career, from 1896 to 1899 she had been arrested and charged 6 times for grand larceny but, she was discharged every time. Unfortunately, such teflon ways did not last long .

Falling in with a circle of serious criminals in New York’s infamous Tenderloin district, May became engaged to jewel thief Eddie Guerin. She went with Guerin to Paris where they targeted the office of American Express for a clean out.

The robbery took place on April 27 1901 and all went according to plan when May and Guerin stole a quarter of a million dollars from the American Express office. Their delight did not last long however. Guerin was arrested and sent to the penal colony of Devil’s Island on Guiana. May managed to evade capture but her freedom was short lived. In a stupid and out of character move, she risked being recognised when she went to Devil’s Island to visit her beloved Guerin. Instantly spotted and identified, she was packed off to Montpellier prison to serve a 5 year stretch.

To make up for her foolishness of getting caught, she devised a plan of escape. Instead of tunnelling out or climbing the walls, May used the old reliable method of blackmail. While languishing in the clink she seduced the prison doctor and ultimately cornered him for his actions. This led to her early release and she hopped on a boat that took her across the channel to England.

While Guerin was still stuck in prison, May put her skills to good use and entered London’s aristocratic society. She targeted Sir Sidney Hamilton Gore for blackmail, but instead of handing over his wealth he put a gun to his head.

Eddie Guerin

Things went from bad to worse for May. It was not long before Guerin too had managed to escape from prison and was en route to London. Sadly, May’s passion for Guerin had faded. Already in a new relationship with another criminal called Charley Smith while Guerin was still locked up, when Guerin landed in London during 1907, a heated argument broke out between the trio. Guerin receiving a gunshot wound to the leg. Both Smith and May were arrested for attempted murder and the Queen of Crooks was sent to serve 15 years in Aylesbury prison.

While she was in prison May met a well known name from her homeland: Countess Markievicz. A fellow inmate, in later life May would remember the Countess as the grandest woman she had ever encountered and admired her courage against oppression. In her autobiography May recalled how ‘No kind of hardship ever fazed the Countess!’

May remembered in her writing how the prison authorities ordered inmates to pray for British troops after the Germans had made a strong push against them during WWI. In her true rebel rigor, Countess Markievicz refused to pray for those in British army uniform and May, along with another female prisoner who was a German spy, followed the role of the Countess, refusing to comply with this demand. As punishment the three inmates were made carry big iron pots full of gruel all around the prison. On this, May wrote,

“While we were doing this, the Countess recited long passages in Italian taken from Dante’s Inferno. The place looked like hell alright!”

When May was released she returned to New York but she was not the same beguiling beauty that had extorted thousands of dollars from rich men. Older and less attractive, more importantly having been caught, she could no longer claim to be that teflon criminal of yore.

May left New York and headed to Detroit where she lived to the point of destitution. She tried cashing in on her exploits by writing articles for the New York American Weekly and in August 1928 she published her autobiography Chicago May: Her Story by the Queen of Crooks. The publication did not sell well and May, who had once made headlines as one of the world’s most dangerous women,  was destined to fade into the shadows of time.

May’s health had declined  and her excessive alcohol consumption didn’t help. She moved to Philadelphia where in 1929 after surgery for an abdominal disorder, the 59 year old May died. The engaging criminal career of the Longford lass who became notorious as Chicago May ended with an unmarked grave in Fernwood Cemetery in Philadelphia.

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