BOOK REVIEW: ‘City of Scoundrels’: Riveting Account of a Dozen Days in 1919 That Helped Shape Modern Chicago

  • Reviewed by David M. Kinchen
BOOK REVIEW: 'City of Scoundrels': Riveting Account of a Dozen Days in 1919 That Helped Shape Modern Chicago
“Be a Chicago booster! Throw away your hammer! Get a horn and blow loud for Chicago! — William Hale “Big Bill” Thompson (1869-1944), mayor of Chicago from 1915-1923 and again from 1927-1931.



Chicago didn’t get the nickname “The Windy City” because of breezes off Lake Michigan or arctic blasts from Wisconsin: It earned that moniker because of its endless (to critics) bragging about what a great place it was. In Gary Krist’s “City of City of Scoundrels: The Twelve Days of Disaster That Gave Birth to Modern Chicago” (Crown Publishers, 368 pages, notes, bibliography, index, glossy photo insert, $26.00, also available in ebook and audio book form) Big Bill Thompson plays the lead role in an account of a fiery aviation disaster in the Loop; a series of bombings directed at real estate agents who sold blacks houses in white neighborhoods; one of the nation’s biggest race riots; a crippling transit strike and a sensational child murder in a city already on the edge of a precipice.


Krist notes that those dozen days in the summer of 1919 provided more excitement than most cities offer in years — but that’s how Chicago is, larger than life and twice as loud! Visitors from all over the world remark what a treasure trove of architecture and culture the city has — and much of it is the work of a man in love with his city, Bill Thompson, who was born in Boston and moved with his prosperous family as an infant to the boomtown that was Chicago in the 1870s. He grew up privileged, but longed to be a cowboy, which he did for several years as a young man. When most men sported bowlers, boaters or fedoras, Big Bill wore a ten-gallon hat, or maybe the five-gallon kind favored by Lyndon B. Johnson, reminding him of his happiest days on the range in the West.


Gary Krist

Gary Krist


In the Epilogue, beginning on page 261 and covering 1920 and after, Krist describes Mayor Thompson presiding over the opening of the Michigan Avenue Bridge on May 14, 1920, billed as the “greatest event since the World’s Fair in 1893.” The $16 million double-decker bridge help create the Chicago we know today. As a resident of Chicago for three years in the 1960s and a frequent visitor since, I’ve noticed the inscription recognizing William Hale Thompson’s role in the bridge, part of reknowned architect and planner Daniel Burnham’s Plan of Chicago, an ultra ambitious scheme to turn a ramshackle collection of ethnic villages into a modern city — at least in the Loop and along the shore of Lake Michigan. Before the bridge opened, Michigan Avenue stopped at the river; the street across the river was called Pine Street and wasn’t anything like today’s Magnificent Mile.


Much of the book is given over to a discussion of Chicago and Illinois politics, including the rivalry between Thompson and Illinois Gov. Frank O. Lowden. Both were Republicans, but they couldn’t have been more different. It may be a surprise to some readers but when Big Bill ruled Chicago, African Americans were overwhelmingly Republican and he courted them and their votes. The only parade of returning veterans he presided over was one of segregated black veterans. Krist notes that the administration of Democratic President Woodrow Wilson was anti-black, as was the local Democratic party, including State’s Attorney (the Illinois designation for district attorney) Maclay Hoyne, who prosecuted far more blacks than whites in the aftermath of the race riots. Hoyne had been defeated by Thompson for mayor and was regarded by most of the “Negro” and “colored” (the 1919 designations) community on the South Side “Black Belt” as hostile to their aspirations.

When 1919 began, Big Bill’s plans for modernizing Chicago and turning the sixth largest city in the world with a population of 2.5 million into “the Metropolis of the World” — construction on the bridge and widening Michigan Avenue had begun in 1918 — seemed to be on course. Within a few months, everything changed, with the crash of the Wingfoot, the transit strike, the rioting and bombings and repeated attacks on the machine politics of Thompson’s machine. The city’s highest ambitions were suddenly under attack by the same unbridled energies that had given birth to them in the first place.
It began on a balmy Monday afternoon when a prototype Goodyear blimp called the Wingfoot caught fire and crashed throught the roof of a busy downtown bank, killing several of the clerks and customers. All told, 13 died and dozens were injured. Within days, a racial incident at a hot, crowded South Side beach spiraled into one of the worst urban riots in American history, followed by a transit strike that paralyzed the city. Then, when it seemed as if things could get no worse, police searching for a six-year-old girl discovered her body in a dark North Side basement.

Krist provides a delightful personal touch with the romantic tribulations of Emily Frankenstein, whose diary reveals conflicted feelings toward her many suitors, including returning veteran Jerry Lapiner. The sections dealing with Emily, Jerry and their families and friends are a welcome relief from the rioting, mayhem, death from the blimp on fire (it was fueled with the same hydrogen that resulted in the Hindenburg disaster in 1937; Goodyear quickly switched to nonflammable but more expensive helium) and “smoke-filled-rooms” politics Krist so ably describes.


The cast of characters in “City of Scoundrels” includes poet and newspaperman Carl Sandburg; fellow newspaperman and satirist Ring Lardner, soon to depart for the East Coast; Edna Ferber, plying her first trade as a newswoman covering the GOP national convention; Ida B. Wells-Barnett, black rights activist and journalist and friend of Jane Addams; Col. Robert R. McCormick of the Chicago Tribune, who hated Thompson, calling him a traitor and agent of Germany for opposing America’s entry into World War I; and many more. I can see this book turned into a Ken Burns documentary. It combines all the elements made famous by Burns: civil rights, war and returning veterans, sports (the Black Sox scandal unfolded in 1919), prohibition, music, with jazz arriving from New Orleans and Memphis, etc.


If you want to understand how Chicago became the city it is today, with all its attractions — and problems — “City of Scoundrels is an excellent introduction.

About the Author

Before turning to narrative nonfiction with “The White Cascade” and his latest book, “City of Scoundrels”, Gary Krist wrote three novels — “Bad Chemistry”, “Chaos Theory”, and “Extravagance” — and two short-story collections–“The Garden State” and “Bone by Bone”. He has been a regular book reviewer for The New York Times Book Review, Salon, and The Washington Post Book World. His satirical op-eds have appeared in The New York Times and Newsday, and his stories, articles, and travel pieces have been featured in National Geographic Traveler, The Wall Street Journal, GQ, Playboy, The New Republic, Esquire, and on National Public Radio’s “Selected Shorts.” His stories have also been anthologized in such collections as Men Seeking Women, Writers’ Harvest 2, and Best American Mystery Stories. He has been the recipient of The Stephen Crane Award, The Sue Kaufman Prize from the American Academy of Arts and Letters, a Lowell Thomas Gold Medal for Travel Journalism, and a fellowship from the National Endowment for the Arts. He lives in Bethesda, Maryland, with his wife and daughter.

Publisher’s website:

Video promoting “City of Scoundrels”:


One thought on “BOOK REVIEW: ‘City of Scoundrels’: Riveting Account of a Dozen Days in 1919 That Helped Shape Modern Chicago

  1. […] Lower North Michigan Avenue exactly what Pine street was? No, not exactly. Pine Street dates back as far as 1834, back then it was a muddy trail leading north of the river to a little […]

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