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Deadly Valentines by Jeffrey Gusfield

Published by Chicago Review Press on April 1, 2012

Deadly Valentines takes its name from Chicago's St. Valentine's Day Massacre in 1929, the bloody conclusion of which is described in the book's prologue. While Deadly Valentines tells the story of Vincent Gebardi, a/k/a "Machine Gun" Jack McGurn, a charming gangster who almost certainly planned and may have participated in that gruesome event, it does so within the broader context of crime and politics in Chicago during the 1920s.

Deadly Valentines is divided into three parts. The first chronicles Vincenzo Gibaldi's life from his arrival in Ellis Island as a Sicilian immigrant in 1906 at the age of four through his family's move to Chicago during the era of Prohibition. As he grows up in Brooklyn, he is instilled with Sicilian values which, according to Jeffrey Gusfield, center upon the necessity of revenge, obedience to a code of honor, and keeping your mouth shut. By the age of sixteen he is calling himself Vincent Gebardi. Later he adopts the Irish-sounding name Jack McGurn to give his boxing career a boost. He gets a different sort of boost when his boxing is noticed by Al Capone, who employs him to guard shipments of bootleg liquor. On a parallel track Gusfield describes the wild and rebellious young life of Louise Rolfe in Chicago.

Part two begins with the murder of McGurn's stepfather, who unwisely competed against the Genna crime family in the distribution of illicit alcohol. Gusfield then shifts the focus away from McGurn to set the stage for Chicago's gang wars, beginning with the burgeoning rivalry between Capone and Dean O'Banion. McGurn returns to center stage in 1926 when he orchestrates a series of murders that Capone has sanctioned. As odies pile up on the streets of Chicago, McGurn moves up to a leadership position in Capone's organization. In 1928, Gebardi hooks up with Louise in a merger of two unstoppable egos.

Part three, appropriately entitled "Massacre," addresses the St. Valentine's Day killings and their aftermath. Impetuous prosecutors look like boobs after predicting with certainty their ability to convict McGurn. Federal prosecutors do only a little better, obtaining a short-lived, absurd conviction of a Mann Act violation -- a conviction justly overturned by the Supreme Court. With Capone in prison for tax evasion and facing constant harassment by police, prosecutors, and rival gangsters, McGurn decides it is time to focus on his golf game. Organized crime is transitioning from bootlegging to gambling and racketeering and McGurn's influence and health begin a steady decline that culminates in a violent death.

Deadly Valentines captures the colorful culture and rapidly changing attitudes of the Roaring Twenties. Gusfield writes in some detail about the growth of jazz and the live performances that (together with the free flowing hooch) made Chicago a swinging town. The hypocrisy of Chicago's news media and the corruption of Chicago's police, politicians, and judiciary are recurring themes. Another is public tolerance, and even a degree of admiration, for celebrity gangsters who, at least, could be counted on to keep the local speakeasy stocked with safe alcohol. Still another is the lust for publicity displayed by the few Chicago police officers who aren't on the take, a desire that causes them to arrest McGurn repeatedly on bogus charges. My favorite theme concerns the eagerness of police and politicians to destroy civil liberties when they can't solve crime by conventional means.

Although Gusfield tells McGurn's story in lively prose, his sentences are occasionally awkward and the writing becomes less polished as the book progresses. Some of the information he provides is redundant. The text is well documented with copious endnotes but the writing doesn't have a heavy, academic feel. There is abundant drama in McGurn's life and Gusfield allows it to shine through in his narrative. He is perhaps too judgmental about Louise's sexual freedom (girls just wanted to have fun even before Cyndi Lauper wrote their anthem); Louise's alleged "hedonism" seems perfectly ordinary when compared to the 90210 crowd of modern times. In addition to being a "gold digger" and a "boozy barfly," Louise is, in Gusfield's view, "morally bankrupt," a harsher judgment than he ever visits upon serial killer McGurn. Why Gusfield reserved his invective for Louise is puzzling. On the other hand, he properly condemns the bluenose view (popular at the time) that blames jazz and other "race music" for the demise of female virtue. On the whole, despite my qualms about Gusfield's treatment of Louise and occasional lapses in his writing style, I would recommend Deadly Valentines to "true crime" fans and to anyone interested in an convincing portrait of a celebrated gangster.


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