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The Gambler King of Clark Street
Michael C. McDonald and the Rise of Chicago's Democratic Machine
1st Edition
Richard C. Lindberg
Other Formats
328 pages, 6 x 9, 30 Illus.

About the Book

The Gambler King of Clark Street: Michael C. McDonald and the Rise of Chicago’s Democratic Machine tells the story of a larger-than-life figure who fused Chicago’s criminal underworld with the city’s political and commercial spheres to create an urban machine built on graft, bribery, and intimidation. In this first ever biography of McDonald, author Richard C. Lindberg vividly paints the life of the Democratic kingmaker against the wider backdrop of nineteenth-century Chicago crime and politics. 

Twenty-five years before Al Capone’s birth, Michael McDonald was building the foundations of the modern Chicago Democratic machine. By marshaling control of and suborning a complex web of precinct workers, ward and county bosses, justices of the peace, police captains, contractors, suppliers, and spoils-men, the undisputed master of the gambling syndicates could elect mayoral candidates, finagle key appointments for political operatives willing to carry out his mandates, and coerce law enforcement and the judiciary. The resulting machine was dedicated to the supremacy of the city’s gambling, vice, and liquor rackets during the waning years of the Gilded Age.

McDonald was warmly welcomed into the White House by two sitting presidents who recognized him for what he was: the reigning “boss” of Chicago.  In a colorful and often riotous life, McDonald seemed to control everything around him—everything that is, except events in his personal life. His first wife, the fiery Mary Noonan McDonald, ran off with a Catholic priest. The second, Dora Feldman, twenty-five years his junior, murdered her teenaged lover in a sensational 1907 scandal that broke Mike’s heart and drove him to an early grave.

            Michael McDonald’s name has long been cited in the published work of city historians, members of academia, and the press as the principal architect of a unified criminal enterprise that reached into the corridors of power in Chicago, Cook County, the state of Illinois, and all the way to the Oval Office. The Gambler King of Clark Street is both a major addition to Chicago’s historical literature and a revealing biography of a powerful and troubled man.



Richard C. Lindberg is a journalist, research historian, and author or coauthor of thirteen books, including Chicago Yesterday and Today;  Shattered Sense of Innocence: The 1955 Murders of Three Chicago Children; Return to the Scene of the Crime: A Guide to Infamous Places in Chicago, and To Serve and Collect: Chicago Politics and Police Corruption from the Lager Beer Riot to the Summerdale Scandal, 1855–1960. He is a past president of the Society of Midland Authors and a 2008 recipient of the Morris Wexler Award, presented by the Illinois Academy of Criminology, for his contributions to the field of criminal justice writing.


The Gambler King of Clark Street is the story of a remarkable and controversial figure who began his career conning railway passengers and reached such a high state of political eminence that his influence was felt in City Hall, the governor’s mansion, and even the White House. Chicago history aficionados owe Richard C. Lindberg a debt of gratitude for providing a deeper understanding of how the city became what it is today.”

—Rose Keefe, author of The Starker: Big Jack Zelig, the Becker-Rosenthal Case, and the Advent of the Jewish Gangster


“This is an immensely important historical book because it fills a critical gap in Chicago and Illinois history. Michael McDonald is mentioned in every history of the period but his life, role, and significance in the development of both crime syndicates and machine politics has never before been fully explored.”—Dick Simpson, author of Rogues, Rebels, and Rubber Stamps: The Politics of the Chicago City Council, 1863 to the Present


“Until now, little was known about Michael C. McDonald and his profound impact in shaping the political-criminal landscape of Chicago. Richard Lindberg masterfully brings McDonald and his world back to life; a world populated by card sharps, bunko swindlers, back-alley characters, and rogue saloon bosses. Michael C. McDonald’s legacy is a degree of civic malfeasance unmatched anywhere else in the country.  As one frustrated alderman lamented, ‘Chicago is unique. It is the only totally corrupt city in America.’ How did Chicago get this way? Lindberg provides us with the answers.”—William J. Helmer, author of Public Enemies: America’s Criminal Past, 1919–1940


Illinois State Historical Society Scholarly Award, Certificate of Excellence 2009
Society of Midland Authors Biography Award 2009

Also of Interest

Shattered Sense of Innocence
Richard C. Lindberg and Gloria Jean Sykes

To Serve and Collect
Richard C. Lindberg

Colonial Ste. Genevieve
Carl J. Ekberg

Prairie Boys Go to War
Rhonda M. Kohl