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The Gambler King of Clark Street

Micheal C. McDonald and the Rise of Chicago's Democratic Machine

Richard Lindberg

Publication Year: 2009

Biography of Michael C. McDonald, nineteenth-century Gambler King of Chicago, who fused the criminal underworld with elements of the city’s supposed political and commercial “Upperworld” into an oily urban machine built on graft, intimidation, bribery, and influence peddling.

Published by: Southern Illinois University Press

Title Page, Copyright, Dedication

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pp. ix-x


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pp. xi-xii

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pp. xiii-xiv

Because there has never been a published biography of Michael C. McDonald, what has been told about the Gaslight Era gambler over the years has been told anecdotally: snippets of information found here and there, daily transcriptions in the press, and the published memories of veteran reporters and contemporaries. Stories were retold and handed down through the generations. It was the...

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Introduction: The Dark City onthe Edge of Civilization

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pp. 1-7

A Chicagoan, writing on the eve of the world's fair 1893, a portentous event that opened the city to the eyes of the world, nostalgically looked back on a simpler age, a time before the Civil War and the remarkable period of industrial expansion following the Great Chicago Fire that doomed the pastoral village life they had once enjoyed to a collection of fragmented and distant memories. They remembered an earlier era when...

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1. A Train Butcher Raising the Wind

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pp. 8-19

The father—like the son—was a whiskey man and a loyal Democrat down to the bone. At the end of old Ed McDonald’s life, his many friends and neighbors from the Near West Side of Chicago who knew him in better days gathered by his bedside, recalling the throngs of little children tugging on his coat sleeves in the summer months. The youngest of the neighborhood...

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2. Brace Games and Bunko Men

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pp. 20-33

The Confederate states demanded that all able-bodied Southern men join the cause, and the cardsharps, pimps, and grifters (confidence men; tricksters) of New Orleans and Natchez were not exempt from duty. In April 1862, with Admiral David Farragut’s fleet pummeling Confederate forts on the Mississippi, the gamblers formed their own volunteer company, the Wilson Rangers, or “Blackleg Cavalry,” and served the cause...

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3. A Department Store of Gambling

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pp. 34-53

Under the gaslight lamps of Clark Street, the betting action was tightly packed from the Chicago River south to 12th Street—the “Black Hole of Chicago,” as one morally proselytizing journal of the day described it. With the deaths of Trussell and Hyman, the location of the gaming houses gradually shifted southward into an integrated district running along Clark Street from...

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4. Tammany by the Lake

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pp. 54-64

In the pre-fire days of Chicago's history, there stood a rather plain-looking, three-story, basement-frame hotel at Wells and Kinzie Streets, brushing up against the Galena and Chicago Union Railroad depot. The political people and all classes of Chicagoans currying favors with the “men who had it in right” knew this dilapidated building as the “Hatch House,” named after...

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5. The People’s Party and the Overturn of Puritan Rule

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pp. 65-74

Joseph Medill and his police superintendent, Elmer Washburn, made a desperate but honest attempt to break up organized gambling, but not for a day did it stop. By means of informants, alarm bells, and other contrivances, the gamblers usually knew in advance when the bluecoats were going to strike. They secreted their dealer boxes and paraphernalia in hiding places, leaving only the...

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6. Bummers, Gutter-Rats, Whiskey Soakers, and Saloon Loafers

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pp. 75-87

One hundred women of social prominence and high moral notions, all of them earnest and inspired workers in the cause of temperance, crowded into the city council gallery the afternoon of March 19, 1874, to pray for the soul of Harvey Doolittle Colvin, the former city treasurer who had campaigned for mayor on a platform of reform and...

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7. The City Hall Swindle

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pp. 88-98

An embittered Michael Hickey was vanquished but full of wrath against a police department he believed had turned its back on a brother officer so that it could heel before the dictates of a vicious criminal. A series of anonymous letters directed to the members of the city council’s Police Committee accused the worthy gentlemen of shirking their duties and pointed out that...

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8. Our Carter

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pp. 99-111

It was McDonald's destiny to be damned as a street thug and called a loathsome criminal—while at the same time he was warmly regarded by influential city attorneys, judges, and politicians as a master organizer who resurrected the moribund Cook County Democratic Party in the decades following the end of the Civil...

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9. Oyster on the Half Shell [Includes Image Plates–Unavailable]

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pp. 112-120

In November 1884, the skin games and bucket shop investment swindles practiced by the Clark Street bunko men answering to Mike McDonald reached the Oval Office in the White House. The exposure of a gigantic confidence game was so infamous in its design and execution by a gang of remorseless Chicago “sharpers” that it made midnight burglary look respectable...

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10. Boodle for the Gang

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pp. 121-135

The hot and sultry weather failed to dampen the enthusiasm of the visiting Democratic delegations that descended upon Chicago in early July 1884 to nominate their party’s candidate for president. A. T. Andreas reported that the festivities “far outrivaled the Republican gathering in point of excitement, enthusiasm, fireworks; the noise of the brass bands and the speeches...

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11. Is He Not a Typical Democrat?

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pp. 136-143

The Citizens’ Association said it “hoped that future generations will learn wisdom from the experience, especially as kindred frauds in other parts of the country are being unearthed and punished at the same time that our community has brought to light and castigated offenders against our welfare and integrity. An epidemic of fraud has been followed by the corrective antidote...

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12. A Flighty and Excitable Woman

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pp. 144-151

Despite the best intentions of Mike McDonald to provide a tranquil setting for his wife “Mamie,” his wheezing, cantankerous father, “Grandpa” McDonald, and the two excitable little boys, Guy and Cassius, in the magnificent mansion at 308 Ashland Boulevard, with its Turkish carpets, hardwood floors, and inlaid grand piano, his efforts brought only more domestic...

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13. Bribing the Gray Wolves for an “Upstairs” Railway

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pp. 152-164

Alfred Trude presented Mike's suit for divorce to judge Jamieson of the Superior Court—certainly no stranger to the McDonald kin. The gambler-politician laid bare his soul, calling Mary “wholly unfit” to be a mother and revealing secret information from the Pinkertons that Mrs. McDonald was “unduly intimate” with Moysant inside the two hotels. It was a time...

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14. The Garfield Park Racetrack War

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pp. 165-174

Mike McDonald's idiosyncratic quest for riches, respect, and recognition from representatives of the “upper world” was congenital—but his alliance with the Chicago netherworld was enduring. He was still the boss gambler, fixer, and all-around rogue, despite his remarkable ascent into the world of high finance and politics and his having built the city an elevated line, presumably...

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15. Electing Altgeld

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pp. 175-189

The state was not through with McDonald. Although he had been acquitted by a partisan justice of the peace in a rigged trial, the Cook County grand jury voted a four-count indictment against the old gambling boss, charging him with an act of bribery. As his term of office wound down, Mayor Washburne was frustrated and angered by the outcome of the Woodman affair. His attempt...

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16. That Little Feldman Girl

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pp. 190-202

The world's fair of 1893 represented the stellar triumph of commerce, industry, the arts and sciences, and humanity’s progress as it marched toward the dawn of a new century. For six glorious months that year, the magnificence of the white alabaster buildings in all their splendor revealed Chicago to the world as much more than a clogged metropolis of smokestacks...

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17. Pearls before Swine: Poetry, Murder, and the McDonalds

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pp. 203-215

The mature, golden years of McDonald's life were at hand—he was healthy, robust, and going about his business in the usual ways. Dora provided him with marital pleasures he had not known in many a year; the period of loneliness was over, and now came a redemption of spirit and the chance to feel young, vigorous, and alive again. Grandpa McDonald passed away...

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18. Betrayal and Death

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pp. 216-224

Exhausted by his labors, Mike McDonald was a living portrait of despair. Looking careworn and deeply troubled, he sat at Dora’s side every day following the tragedy in the Omaha Building. The sight of his wife thrashing about violently on her bed and muttering nonsense deeply affected him. The jailhouse cynics chuckled and said that she was either the greatest...

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pp. 225-231

The woes of Dora Feldman did not end with the close of the trial. The widow never made it to Palestine or Florida, nor did she fulfill a promise to build a hospital, aid sickly children, or erect a monument to the eternal memory of her late husband. Rather, Dora chose to remain in Chicago for the next eighteen years contesting the will and battling Mary Noonan and...

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Epilogue: A Legacy of Corruption

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pp. 232-236

The prevailing view of Chicago as a metropolis ruled by political mischief makers, wire-pullers, and underworld figures operating in the shadows was engrained in the public mind decades before the bloody reign of Al Capone—the name most often equated with organized criminality in the Windy City. Arguably, it was Mike McDonald, and not Capone, who was the...

Appendix 1: Organized Gambling in Chicago during the Reign of Mike McDonald, 1868–1888

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pp. 239-243

Appendix 2: Organized Gambling and Horse Racing Poolrooms in Chicago, Post-McDonald Period, 1889–1900

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pp. 244-251


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pp. 253-276


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pp. 277-282


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pp. 283-293

E-ISBN-13: 9780809386543
E-ISBN-10: 0809386542
Print-ISBN-13: 9780809328932
Print-ISBN-10: 0809328933

Page Count: 352
Illustrations: 25 b/w halftones, 5 line drawings
Publication Year: 2009

Research Areas


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Subject Headings

  • Irish American criminals -- Illinois -- Chicago -- Biography.
  • McDonald, Michael C. (Michael Cassius), 1839-1907.
  • Political culture -- Illinois -- Chicago -- History -- 19th century.
  • Chicago (Ill.) -- Politics and government -- 19th century.
  • Gamblers -- Illinois -- Chicago -- Biography.
  • Political corruption -- Illinois -- Chicago -- History -- 19th century.
  • Businessmen -- Illinois -- Chicago -- Biography.
  • Chicago (Ill.) -- Biography.
  • Politicians -- Illinois -- Chicago -- Biography.
  • Democratic Party (Chicago, Ill.) -- History -- 19th century.
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