Bullets, Ballots And Bribery Define Early Illinois Gambling History

Written By Robyn McNeil on October 21, 2022 - Last Updated on February 16, 2023
illinois gambling history first chicago crime lord

The history of gambling in Illinois is long and storied, with games of chance in play even before the state joined the union in 1818.

In this PlayIllinois series, we feature people and events from the early days of Illinois gambling.

Gambling quickly gains ground (and criminal interest) in Illinois

In Illinois’ early days, Americans generally accepted gambling as entertainment. But, when gambling commercialization took over, criminality followed, and the pastime became associated with laziness and vice —particularly among the upper classes. By 1830, Chicago’s protestant clergy denounced the activity, and city officials followed suit, jailing the owners of at least two local betting parlors.

Still, gambling appealed to the working class, providing a sense of independence and contrast to their low-paying, micro-managed work. The competition also offered a chance to take risks in a way not usually accessible to men of lower social stature.

As a result, Illinois bettors wagered on everything from checkers to card games, backgammon, horse racing, boxing, and policy (similar to a lottery). And by the 1850s, betting markets expanded to include rat and cock fights. Business-minded folk established hundreds of gambling establishments in the state by this time, particularly in the city core. Illinois Gambling was already big business, and gambling payrolls, rental income, and related spending became economically important to the state.

Of course, the burgeoning money-making potential of gambling in Illinois also made it appealing to entrepreneurs and the criminally minded.

Michael Cassius McDonald, Chicago’s first true crime lord

Michael Cassius McDonald was born in Niagara, New York, in 1839, to Irish immigrants. He first came to Chicago in 1854 at 15 years old and returned two years later. This time, he stuck around, selling candy and necessities to train passengers as a “train butcher” and swindling along the way.

During this period, McDonald learned to play cards and used his keen observation skills to decipher his opponents’ body language as they bluffed and wagered away. It was a skill that would serve him well over the years to come.

During the Civil War, McDonald devised a “bounty broker” scheme to defraud the army of its enlistment reward ($300 or $500, depending on the source). He organized enlistees to sign-up under numerous false aliases. Then he’d collect a portion of the bounty in return for shielding the fraudster from legal consequences.

Once the war ended, McDonald financed a traveling faro bank, said to be the most successful in Chicago.

What is Faro? A blue-tinged crackle background with images of playing cards in on either side and a text description of the game in the center.
Faro, a 17th-century card game, was extremely popular during the early years of the US.

With the profits from his various schemes, McDonald soon opened his first gambling house at 89 Dearborn Street. By 1868, the Chicago Tribune began reporting his arrest(s) for criminal conspiracy and the running of gambling dens.

The following year, he was arrested again for stealing $30,000 from a Chicago Dock Company cashier, who had allegedly given McDonald the money. McDonald spent three months in jail before being acquitted at trial. However, the proceeding’s expense impacted his ability to pay for police protection.

The shortfall meant his gambling operation suffered frequent raids, and McDonald faced regular arrests and fines. As a result, he developed a lifelong disdain for law enforcement.

A syndicate rises from the ashes of the Great Chicago Fire

In 1871, McDonald lost everything in the Great Chicago Fire. However, he raised enough a few short weeks after to establish a saloon at the corner of State and Harrison streets. There, illegal card games were a popular attraction.

Two years later, McDonald funneled that success into The Store, a four-floor gambling parlor that proved an immediate success. The Store’s games were rigged but combined with its saloon, hotel, and elevated dining experience, it became a favored Chicago attraction.

Around this time, McDonald started receiving “tribute” from other gambling houses and brothels in exchange for protection from the law. At the same time, he bribed complicit law enforcement and politicians with exposure to cement their future cooperation. This extortion and his subsequent criminal activities are considered the beginning of organized crime in the windy city.

Ballots, bullets and bribery

McDonald’s syndicate brought in big money and critique in the local press. The attention, however, only contributed to his lore.

McDonald gets credit for founding “the gambler’s trust,” Chicago’s first ‘political machine.’ Some even say his political activities laid the foundation for today’s Democratic party.

In any case, he organized Harvey Doolittle Colvin’s successful 1873 mayoral campaign. Colvin’s win gave McDonald significant influence over the city. He later helped Carter Harrison Sr. come to power in 1879.

In between, McDonald hit a mayoral snag with the election of reformer Monroe Heath in 1876. Heath ordered repeated raids on McDonald’s gambling ventures, including McDonald’s apartment, located on the upper floor of The Store.

McDonald wasn’t home at the time of the raid, but his wife, Mary, was. Mary, who was as big a fan of police as her husband, shot at officers involved in the raid. Here, sources differ on whether Mary killed an officer or was simply charged with attempted murder. Regardless, despite her arrest, the authorities ruled the shooting justifiable. It’s been said that McDonald influenced the outcome by bribing a judge.

Fortunately for McDonald, Harrison was reelected in the next election.

Millions earned through gambling, fraud and influence

At the peak of McDonald’s authority, people called him “King Mike” due to the coalition he built between Chicago politicians and the gambling world. The alliance funneled illegal gaming dollars into Democratic Party operations and offered insulation from police interference for those who paid.

In 1882, McDonald attempted to gain more influence over elections and persuade the passage of favored municipal ordinances when he bought the (short-lived) newspaper, The Chicago Globe. For his next big move three years later, he started a bookmaking operation that controlled gambling at racetracks in Illinois and Indiana, including Garfield Park.

By then, McDonald was a multimillionaire, his fortune attributed to gambling revenues and sweetheart deals. In many cases, his shell companies even failed to provide the services promised.

For example: in the late 1880s, McDonald received approval to paint the city’s courthouse with a protective compound later found to be worthless. McDonald bribed the Cook County Board of Commissioners and Chicago City Council to get the contract and charged exorbitant fees for the work. Depending on the source, he billed anywhere from $128,000 to 180,000 for a $30,000 project.

While some went to prison for the fraud, McDonald escaped legal punishment. However, a newspaper investigation caused a scandal, tarnishing McDonald’s image. In the aftermath, he temporarily stepped away from public life, even going as far as selling The Store.

King Mike hangs up his crown

Near the end of the 1880s, McDonald invested in the transit company of Charles Yerkes and began to push plans for Lake Street Elevated rapid transit line. After bribing 13 members of the Chicago City Council, they approved an ordinance allowing the construction. In early November 1893, passenger service began on what gambling circles dubbed “Mike’s upstairs railroad.”

By the mid-1890s, McDonald took leave of the gambling hustle. In his absence, other criminal elements divided his monopoly.

McDonald died in 1907 of natural causes. That said, some say the actions of his second wife, Dora, may have hastened his departure (but that’s another story). At the time, he had a $2 million estate (that’s $63,015,106.38 today).

McDonald rests in a mausoleum at Mount Olivet Cemetery in Chicago.

Appearances in popular culture

Pale yellow book cover features men, women and children dressed in fancy dress clothes from the late 1920s ascending the gangplank of a Mississippi River Boat
Show Boat, Edna Ferber

Notably, McDonald’s refined yet elaborate fashion inspired the character Gaylord Ravenal in Edna Ferber’s 1926 book Show Boat. The book was adapted into a musical of the same name, which had several reimaginings.

Some also credit McDonald as the originator of the line, “there’s a sucker born every minute.

While many have associated the famous aphorism with PT Barnum, there’s no evidence Barnum uttered it. Not even his biographer was able to verify the claim. He even argued Barnum was not a man to put down his audiences that way.

But, according to Gem of the Prairie: Chicago Underworld (1940) by Herbert Asbury, as McDonald was outfitting The Store, a business partner shared concern over the great many roulette wheels and faro tables installed. Allegedly, McDonald soothed his fear, saying, “Don’t worry about that, ‘there’s a sucker born every minute.'”






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Robyn McNeil

Robyn McNeil is a Nova Scotia-based writer and editor. She lives in Halifax in an empty nest with a mischievous cat and a penchant for good stories, strong tea, cheeseburgers, yoga, graveyards, hammocks, gardening, games, herb, and hoppy beer.

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