The Queen of Crooks

Naula O'Faoilain's new novel is abased on the story of an interesting Irish woman who stole her family money from her poor Longford household to go to America to become a mobster. Ben Macintyre finds it neither a novel nor a biography

The Story of Chicago May

Nuala O'Faoláin. Riverhead Books, €24.95

Professional crooks are as hard to track down when dead as they are tricky to trace in life, and for similar reasons. Criminals tend to be wary about leaving clues; when they do spill the beans, it's usually for money or self-exculpation or revenge. Being dishonest, they tend to lie – but inconsistently. By the end of the nineteenth century, conmen, safecrackers, mobsters and their molls had attained a seedy glamour, and many wrote memoirs with titles like I Was a Bandit and Why Crime Does Not Pay. (A female gangster named Sophie Lyons wrote that last book, which, so far from warning against the perils of crime, reads like a detailed advertisement for various forms of felony.) Such accounts tended to be racy, self-inflating, unconvincingly moralistic and extremely unreliable.

Nuala O'Faolain has waded undaunted into this treacherous biographical terrain with a spirited account of the life of Chicago May, one of the few notorious women in the male-dominated rogues' gallery of American criminals. May Duignan was born into poverty in County Longford in 1871. At the age of 19, she stole the family savings and headed to the United States, beginning a life of crime that would include prostitution, con artistry, blackmail and violence, with plenty of foreign travel thrown in. Quite why May turned to the bad is unknown. This was not something she discussed, or even appeared to think about much. In her own book, Chicago May, Her Story: A Human Document by 'The Queen of Crooks' published in 1928, shortly before her death, Duignan described where she went, what she did and whom she did it to, but not her feelings. Despite the title, May's "humanity" was not a subject she wished to explore.

O'Faolain, the author of two memoirs and a novel, fills the yawning gaps with her own imagination. As she concedes, May's emotional reticence, her "lack of self-consciousness" is a negative quality to the biographer, whom it condemns to incessant speculation. O'Faolain has therefore constructed her book from bricks of facts – some reliable, some dodgy – held together with the mortar of conjecture and wishful thinking. The result is so spackled with conditionals that it makes for awkward reading: O'Faolain "imagines", she "supposes", she "believes", in order to round out this unfinished character. "That's what I think she must have been doing", she declares, or tells us what "May might have thought". This is neither a novel nor a biography; there are no footnotes or bibliographic citations, and little to depend on save O'Faolain's determination to drag this character out of the murky past: "Off she sailed with her red-gold hair and blue eyes and raucous laughter and tough-as-nails mannerisms and reckless energy." Chicago May took her moniker from a few years spent in that city, but like most crooks she was rootless, feckless and unstable. She floated from Nebraska to New York to Paris with a succession of grim and violent men, spending money wildly when she had it, prepared to do anything to get it when she was short. Mostly what she did was sell her body, although O'Faolain (and Duignan herself) delicately preferred to consider her "a badger" – a woman who lures men with the promise of sex and then robs them.

Was May an outlaw in the traditional mould, a glamorous good-time girl? Or was she a casualty, ruined by the sexual demands of men and the cruelties of society? O'Faolain, rather uneasily, offers us both portraits. One moment May is admired for her high-rolling bravado: "She was famous for her method of biting the stones out of men's scarf pins while she amorously pretended to bury her face against their chests." But the next, beaten up yet again, she is to be pitied and mourned. We follow her as she moves from town to town, from man to man, from job to job, jolting from sympathetic heroine to tragic victim and back again. "She has to arrive in some town, pull herself together, lift her bag, and walk down the steps to begin her boring, alienating, uncomfortable, dirty and dangerous work. It was a gallant life in its way, and extremely lonely." O'Faolain is best when looking through the prism of May's unlovely life to a wider world.

Duignan, like so many other young immigrants, emerged from priest-controlled peasant Ireland to a place of unrestrained decadence, of sexual license, cheap gin and the dazzling corruption of the Tenderloin. O'Faolain's own troubled Irish family background (the subject of her memoir Are You Somebody?) is touchingly recalled as she links May's fate to that of her own unhappy brother, Dermot, who drank himself to death.

The law caught up with May in England, where she was sentenced to 15 years for the attempted murder of a former boyfriend. Imprisoned with her in Aylesbury was Constance Countess Markievicz, the Irish nationalist who played a starring role in the Easter Rising.

With an almost audible wrench, the author brings them together. The countess and another convict were set to work washing dishes: "I feel certain that this other convict was May." From here, Duignan is invested with a political cause, though there's little evidence she cared deeply about Irish nationalism or, for that matter, about Ireland.

May's end was bleakly poignant. Deported to the United States after serving ten years of her sentence, the middle-aged jailbird drifted back onto the streets and would surely have died there had her case not been taken up by August Vollmer, a leading police official and judicial reformer, who urged her to write her life story. She went briefly straight.

"Nothing can turn my path," she declared.

But the book failed to make her fortune, and soon she was back to her old ways. Soon after that, she was dead, expiring in a hospital ward on the day she was to have married an old flame from her past.

May Duignan's autobiography is remarkable as much for what it fails to say as for what it reveals. There is little of the bogus handwringing that accompanies so many books of the genre. May tells her story with cool inflexibility.

This was one tough cookie and, as O'Faolain points out, "she never makes the slightest effort to win the reader's sympathy". The winning of sympathy for May Duignan is O'Faolain's self-appointed, well-meaning and somewhat thankless task. Certainly one doubts whether May herself would have been grateful.

O'Faolain has tried to capture her subject by making her into a symbol: of oppressed womanhood, of Irish nationalism, of the immigrant experience, of the traumas within O'Faolain's own family. But May left so little evidence, so few emotional fingerprints, that, for all O'Faolain's careful weaving, she slips through the net. Chicago May is still on the run.p

©The New York Times