The woman deemed the most perilous in the world.

Earning the title of “The Most Dangerous Woman in the World” demands a life fraught with more secrets than confessions, constantly evading those in pursuit—be it the press, law enforcement, or those wronged by your actions. This was the reality for Mary Ann Duignan, also known as May Churchill Sharpe, or famously as “Chicago May,” a notorious figure in the criminal underworld of the early 1900s, shuttling between Europe and America.

Born in Ireland in 1871, Mary Ann Duignan felt the pull of a life beyond the ocean’s horizon and set out in 1890, a time when emigration was common among post-famine Irish. she absconded in the dead of night, taking her family’s savings with her. she traversed the Atlantic in luxury, funded by ill-gotten gains, reveling in the chaos she sowed among the elite.

Arriving in New York,, where she married Dal Churchill, the first of her several brief unions. After his death, she adopted the moniker “Chicago May” upon settling in the bustling city. Despite the fair’s promise of economic revival, opportunities remained scarce, prompting many, including May, to turn to sex work for survival. Yet, May’s ventures extended beyond mere transactions, as she honed her skills as a con artist, luring victims with promises of intimacy only to rob them blind.

Despite her adeptness in crime, May knew when to flee the scene, eventually returning to New York and continuing her exploits as both a con artist and a chorus girl. Her schemes, now incorporating blackmail, spanned across North and South America, affording her a life of opulence marked by lavish possessions and high society connections.

In London, she partnered with Eddie Guerin, engaging in criminal escapades that led to imprisonment in France. Despite briefly securing her release through manipulation, May found herself back behind bars after an attempt on Guerin’s life.

May’s life reflects the harsh realities and limited choices faced by women in her time, navigating a world where marriage or emigration were often the sole options for survival. Yet, her actions also speak to a defiance against societal constraints, challenging norms and expectations at every turn.