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Chicago Assassin: The Life and Legend of 'Machine Gun' Jack McGurn and the Chicago Beer Wars of the Roaring Twenties

Richard J. Shmelter


The city of Chicago led the nation in gangland violence created by the "Noble Experiment" known as Prohibition, and throughout the Roaring Twenties and beyond, it produced many infamous criminals whose names will forever be a part of America's criminal history.

"Machine Gun" Jack McGurn was one of the most colorful and lethal characters whose exploits made the Windy City synonymous with organized crime throughout the turbulent era. Chicago Assassin documents the rise and fall of one of the period's most compelling underworld denizens.

He was born Vincenzo Gibaldi in Licata, Sicily, at the beginning of the twentieth century and, with his parents, became part of the mass exodus by Europeans seeking a better life in the perceived utopia across the Atlantic known as America. The Gibaldis settled in Brooklyn, where Vincenzo spent much of his early life until a senseless act of violence tore his world apart. In a case of mistaken identity, his beloved father was murdered, and from that day forward, deep in his soul, there burned the quest for revenge.

Some years later, Vincenzo's mother remarried a grocer, Angelo DeMora, and the new family moved to Chicago to make a fresh start. Vincenzo succeeded in his new surroundings, thanks to his friendly personality and outstanding athletic prowess. The handsome, congenial youth quickly mastered every sport he attempted, and by his late teens he had become one of the top welterweights in Chicago. Deciding to turn professional, Vincenzo Gibaldi adopted the name Jack McGurn, an Irish-sounding name more suited to a sport dominated at the time by that ethnic group.

While "Battling" Jack McGurn was attempting to make a name for himself in the ring, his stepfather, Angelo, was working hard in the grocery store he owned in the Little Italy section of the city. The notorious Genna brothers controlled the manufacture of bootleg alcohol in Little Italy, and they bought the sugar needed to make their illicit product from McGurn's stepfather. But when they discovered the grocer was also selling sugar to other bootleggers, the Genna brothers targeted him for assassination and brutally cut him down in front of his store.

Once again, the young Italian had to cope with the horrific loss of a father. This time, however, his quest for vengeance erupted with extreme violence. He went to Brooklyn, where he fatally shot two of his biological father's killers and seriously wounded another, then returned to Chicago, where he eliminated those responsible for the murder of his stepfather. It was at this time that Jack McGurn caught the eye of America's premier gangster, Al Capone.

After a sterling apprenticeship with a Capone-controlled satellite called the Circus Gang, McGurn realized that fate had determined his life's work. He eventually earned a reputation as Chicago's most feared and notorious gangland assassin, with more than twenty kills to his credit during the city's bloody Beer Wars. It is interesting to note that the weapon of choice for the man known as "Machine Gun" Jack was actually a revolver—his nickname, like those of most criminals of the day, was concocted by a newspaper reporter looking for a catchy moniker that would make good copy.

Jack McGurn also has been forever linked to the most notorious slaying in gangland history—the St. Valentine's Day Massacre. Within these pages is new evidence that brings to light in detail Jack McGurn's involvement in the slaughter and its aftermath.

And no story set in the turbulent decades of the 1920s and '30s would be complete without the gorgeous women who sought their thrills from these dangerous yet intriguing men. Like most of his contemporaries, Jack McGurn could have his pick among countless beautiful young females, but one became not only his lover but his soulmate, as well. Louise Rolfe was the quintessential jazz baby, and she played a major role in McGurn's life, earning a bit of immortality herself along the way.

Of all the gangsters who became household names during the Roaring Twenties and Prohibition—and whose legends continue today—"Machine Gun" Jack McGurn is arguably the most compelling, for his classic good looks, love of family, athletic ability, and calculating criminal mind made him the template for the good-boy-gone-bad films that have been a staple of American culture since the 1930s.

RICHARD J. SHMELTER is a writer and researcher specializing in sports and American crime history from the 1890s to the 1940s, especially the Prohibition era. He is a member of the North American branch of the International Association of Crime Writers and the American Crime Writers League. The author of The Browns: Cleveland's Team, he lives in Sagamore Hills, Ohio.

$24.95, Hardcover
ISBN-10: 1-58182-618-4 (Hardcover)
ISBN-13: 978-1-58182-618-0 (Hardcover)
Hardcover Available April 2008

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