Michael Cassius McDonald (c. 1839 – August 9, 1907) was a crime boss, political boss, and businessman based out of Chicago. He is considered to have introduced organized crime to the city, and to have also established its first political machine. At the height of his power, he had influence over politicians of all levels in the state of Illinois.

McDonald permanently settled in Chicago as an adult sometime after the American Civil War. McDonald ran gambling parlors in the city. As a crime boss, he developed a system in which he would guarantee the city's gambling dens and brothels protection from interference in exchange for payment. A Democrat, McDonald was involved in the city's politics, and, at his peak, wielded massive influence over it. McDonald was also involved in numerous business ventures. He was one of the principal figures behind the Lake Street Elevated Railroad Company, which built the Lake Street Elevated rapid transit line in Chicago.

In the mid-1890s, McDonald retired from the gambling business, and his gambling circuit deconsolidated under the leadership of several different crime bosses.

Early life and family McDonald was born in Niagara Falls, New York in 1839.English, p. 73 McDonald and his family lived in an Irish enclave of Niagara County, New York.

McDonald father was Edward "Ed" McDonald.Lindberg 2009 pp.8–9f As a young man, Ed McDonald had immigrated to Canada from County Cork, Ireland as a stowaway.Pucci 2019 p.13 The elder McDonald then worked in Quebec as a laborer, before immigrating again into the United States, settling in Niagara County in 1837. Ed McDonald became a loyal member of the Democratic Party which was relatively new at the time.

McDonald's mother was born in Limerick, Ireland with the maiden name of Mary Guy. She was a religious woman. She wed Ed McDonald in Niagara, and had three children, Michael, Mary, and Edward Jr. Functionally illiterate, she would require her children to attend parochial school during the week and mass on Sundays.

McDonald's father was a strict disciplinarian who regularly administered corporal punishment to his children for misbehavior.Pucci 2019 pp.13–14

The younger McDonald, despite his father's urging, refused to pursue a job as a bootmaker's apprentice.Lindberg 2009 p.11Pucci 2019 p.14

In the autumn of 1854, a fifteen year old McDonald traveled to Chicago on a two-week trip.Lindberg 2009 p.12 He returned to Chicago two years later along with four friends from school. In Chicago he worked as a "train butcher", selling candy and goods to train passengers. He committed a number of swindles while working. In 1860, he quit train butchering, and moved to New Orleans.Lindberg 2009 p.14 In New Orleans he took note of the gambling culture there.

During the American Civil War, he organized groups of fraudulent enlistees who enlisted under false aliases multiple times to collect the $500 bounties. In this scheme, he colluded with army deserters, who had agreed to turn themselves in, to then reenlist, and then split the commission which McDonald received for recruiting them.English, p. 74

Return to Chicago Sometime after the American Civil War he returned to Chicago. After having spent some time financing a traveling faro bank, in 1867, McDonald opened his first gambling establishment at 89 Dearborn street. In November 1868, the Chicago Tribune reported McDonald's arrest, along with national billiards champion John McDevitt and two other gamblers, for criminal conspiracy and the running of gambling dens after having apparently fleeced an intoxicated man out of more than $400 while playing faro. In 1869, he was arrested for allegedly stealing $30,000 from an assistant cashier of the Chicago Dock Company. The cashier had given the money to McDonald to finance his gambling operations. McDonald was unable to afford bail, and, consequentially, spent three months in prison prior to being acquitted at his trial. Because of the expense spent on his criminal trial, McDonald had trouble paying protection payments to the police, and, as a result, his gambling operation was frequently raided, and McDonald was repeatedly arrested and fined. This fostered McDonald's lifelong disdain for police.

McDonald had a common-law marriage, until his common-law wife ran away to join a convent in St. Louis.

In the 1871 Great Chicago Fire, McDonald lost the entirety of his real estate and businesses, which were uninsured. Within a few weeks of the fire, McDonald managed to raise enough funds to establish a saloon at State Street and Harrison Street, where illegal card games were featured.Pucci 2019 p.33

On December 5, 1871, McDonald married Mary Ann Noonan, a divorcee with two children from her previous marriage.Pucci 2019 p.34

Criminal and political rule in Chicago In the mid-1870s, McDonald would engage in a number of ventures which would make him a multi-millionaire by the mid-1880s.English, p. 78

In 1873, McDonald opened a gaming parlor named "The Store".Pucci 2019 p.36 It was a four-floor building located at the northwest corner of the intersection of North Clark Street and West Monroe Street. This was McDonald's first major business venture.English, p. 75 "The Store" proved to be an instant success. The games were rigged, but it became a gambling mecca and a major attraction in the city. It contained a saloon, hotel, and a fine dining establishment in addition to its games. Some sources attribute the origin of the famous phrase "there's a sucker born every minute" to McDonald, who reportedly said it in response to concerns a crony voiced about whether the parlor could attract enough customers to fill the large number of gaming tables in the venue.

McDonald developed a system under which he was paid tribute by the city's gambling establishments and brothels, and, in exchange, would use his influence to ensure that they could operate without police interference.

McDonald's criminal activities in the 1870s and 1880s are considered to mark the beginning of organized crime in the city of Chicago. He is considered to have been Chicago's first mob boss. His crime syndicate would make him significant amounts of revenue. He would also receive regular critical press from many of the city's newspapers, contributing to his notoriety.

Another profitable venture which McDonald ran was a bail bond business. Through this business, he was also able to garner connections with many of the city's criminals.English, pp. 77 and 78

McDonald became involved in Chicago's politics, forming a political organization that was dubbed the "gambler's trust". This is considered to have been Chicago's first political machine. Some consider his political activities to have laid the base upon which the city's modern Democratic Party was built. In 1873, by which time McDonald was well-established in the criminal underbelly of Chicago, he organized the successful mayoral campaign of his close friend Harvey Doolittle Colvin. Colvin's victory garnered McDonald great influence in the city. McDonald, thus, gained a friend in the mayor's office, as opposed to the previous anti-gambling mayor Joseph Medill, who had made many efforts at reform in the city. McDonald's political influence experienced a setback when Chicago elected reform mayor Monroe Heath in 1876. However, a McDonald-backed candidate would soon return to the mayor's office. Appreciating his liberal views on liquor consumption and gambling, McDonald supported Carter Harrison Sr. for mayor in the 1879 Chicago mayoral election,Linberg 2009 pp.102–104 playing a major role in Harrison's election as mayor. McDonald would come to have many of the city's politicians under his influence. By the peak of his influence, he would receive the nickname "King Mike", and would brag that he "ran the town" and had the city's police department "under his thumb". McDonald established an alliance between the city's gambling interests and its politicians which saw some illegal gaming revenue used to fund Democratic Party political operations. As a political boss, he became so powerful in the city's Democratic Party, that, for some time, he held an effective veto over the selection of candidates to be the party's nominees for election in the city.

While mayor, Monroe Heath ordered raids on McDonald's gambling operations. On November 23, 1878, there was a police raid on McDonald's personal apartment, located on the third floor of "the Store". McDonald was not home, but his wife Mary was. Mary hated cops, and fired a gunshot from a pistol that pierced a police officer's coat, but missed him. She also dropped an iron bar down the stairs onto another policeman, injuring his back, but despite some later claims that she killed a cop during the raid, an article in the Chicago Tribune states otherwise."Mrs. Mike M'Donald," Chicago Tribune, November 24, 1878. She was arrested and charged with assault with intent to kill, but on December 2 the judge dismissed the case because he said the police violated the law by raiding a private residence without a warrant."The Courts: Mrs. M'Donald" Chicago Tribune, December 3, 1878.English, p. 80 Amid these raids, he had his saloon license briefly revoked, but it was restored within a week.

After the shooting incident, McDonald moved his wife and two children out of "The Store" and into a mansion that was built for them on Ashland Avenue, near Mayor Harrison's own residence. However, months later, Mary McDonald left her husband to pursue a relationship with a notable minstrel singer in San Francisco. McDonald went to San Francisco to pursue them, and this was treated as an item of great amusement by Chicago's newspapers. Ultimately, he found his wife and her lover, and Mary asked McDonald to take her back. The two returned to Chicago.

In 1882, McDonald was indicted for running a gaming house, but was able to get off, in part due to bribed witnesses.

In 1882, McDonald bought the short-lived newspaper the Chicago Globe. He sought to utilize the newspaper to influence both elections and to persuade the passage of municipal ordinances that he favored.

At a private meeting held at the White House, McDonald was able to convince Chester A. Arthur to pardon a colleague of his who had been convicted in a pyramid scheme.

Around the year 1885, McDonald created a book-making syndicate which held control of gambling at racetracks in Chicago and Indiana. The most notable racetrack was Garfield Park Racetrack.

In 1885, McDonald claimed to be retiring from the gambling business. In early 1885, McDonald also said he was going to retire from politics. Both would prove not to be the case, and he would remain involved in politics until his death and would not retire from the gambling business until roughly a decade later.Lindberg 2009, p. 229

In February 1885, a month before the 1885 Chicago mayoral election, a grand jury found McDonald's right-hand man Joseph Mackin and others with connections to Harrison guilty of election fraud in the 1884 elections, creating a scandal for Harrison ahead of being up for reelection. Despite the fact that no personal wrongdoing on Harrison's part was involved in these charges, the charges against Mackin and others compounded with the preexisting rumors relating to Harrison to foster a public sentiment that challenged Harrison's popularity.Labor and Urban Politics: Class Conflict and the Origins of Modern Liberalism in Chicago, 1864-97 Front Cover Richard Schneirov University of Illinois Press, 1998 (pages 166-67) While he won a narrow reelection in 1885, the loss popularity from these scandals contributed to Harrison's decision to not seek reelection to a fifth term in the 1887 Chicago mayoral election.