Michael Cassius McDonald was born in Niagara Falls, New York in 1839.  He died in 1907.  His father was from Cork and wanted his son to be a bootmaker.  The mother of Michael Cassius McDonald was a religious woman and born in Limerick.  As the son passed breath, met people and did whatever happens in a life, he became rich.  On his death his estate was worth two million dollars.  The temptation amongst writers is to think of organised crime in Chicago beginning with Italian gangster Big Jim Colosimo.  The link between Colosimo and Al Capone is neat and direct, a simple succession of three.  Johnny Torrio succeeded Colosimo and Capone followed Torrio.   Under Torrio the gambling and prostitution business expanded to include bootlegging.  Capone consolidated, vigorously defended the empire and relished his celebrity.  The next generation successors to Michael Cassius McDonald were not the Irish tough guy bootleggers that in the 1920s controlled the north side of Chicago.  Dion O’Bannion appears to have graduated without any interim steps from rough house crime to bootlegging.   

Rather than machine gun toting gangsters, McDonald was succeeded by two crooked aldermen called John ‘Balhouse’ Coughlin and Michael ‘Hinky Dink’ Crenna.  These two officials created an open ward or district where they allowed gambling and prostitution to prevail.  Something similar happened in Soho in London.  The two aldermen ran their own saloons that offered gambling.  If they did not dominate the market, they were operators.  More important, they took a percentage from the other crooked establishments.  Crime and corruption had existed before McDonald but large scale integration of crime and politics was a step forward.  His gambling operation required cash to be paid to cops and politicians.  The tradition of wholesale corruption would have happened without him as it did elsewhere in the USA.  Whatever the national trend McDonald has to be given credit for setting it all in motion in Chicago.

The teenage McDonald left home and took a job on the Michigan Central Railroad where he sold magazines and confections to passengers.   Perhaps he became convinced that he had superior survival skills to others, and maybe he also learnt how to understand and take advantage of people. One or more of the train journeys took him to New Orleans.   McDonald saw impressive saloons and gambling houses and decided that he wanted to build something similar.  This sounds like legend rather than fact but nothing exists to prove the legend wrong.   Although not a gambler, McDonald was earning a living from gambling from 1855.  His critics state that McDonald was willing to rig games to improve his profits.  

Five years later in 1860 the opportunist McDonald set up the Corcoran Illinois Irish Brigade.  McDonald recruited Irish men to join the Union Army and fight in the Civil War.  The scam was this.  McDonald encouraged his recruits to enlist, desert and then enlist again.  McDonald would receive a commission each time a recruit enlisted.  The recruit was given a percentage of the commission.  McDonald opened his first stationary gambling establishment in Dearborn Street and in 1867.   Before that he had managed a travelling faro bank.  Faro is a card game that was popular in the 19th century.  Wyatt Earp ran a gambling saloon and was a skilled faro croupier.  The gunfight at the OK Corral has been interpreted as a consequence of a power and business dispute in Tombstone, Arizona.  Earp was a tough guy and kept the law but there are similarities with his behaviour and that of subsequent gangsters.  There are still people around that understand the rules of the complicated card game faro.  I am not one of them.  The extent to which the Civil War scam rather than the travelling faro bank helped Michael Cassius McDonald raise the necessary capital and plant gambling business roots is disputed.   What we do know is that the Civil War recruitment scam contributed to growing funds.

If in 1873 the profits from the gambling house in Dearborn Street had swelled previous funds, there would have also been other schemes or scams contributing to the expanding fortune of McDonald.  He had been in the gambling business for fifteen years and now had enough cash to open a swanky four-storey gambling emporium called the Store.   The gambling took place on the second floor.   The Store also had a saloon, hotel or boarding house and an upmarket restaurant.  The Store was designed to attract affluent gamblers that would stake heavy bets and pay high prices for the food and drink.  Partners of McDonald worried that the fittings in the Store were too extravagant and the scale of operations too epic.  The partners were concerned that future receipts would not cover the investment.  ‘Don’t worry about that,’ said McDonald.  ‘There’s a sucker born every minute.’

Somebody had to create the cliché, and McDonald has been given the credit.   The patrons of the Store were males only.  The gambling available to them included the card games faro and poker.  Dice enthusiasts had the option of playing craps and chuck a luck.   Alternative gambling enterprises surrounded the Store and these accommodated those customers unable to meet the betting stakes and prices that prevailed in the Store.  The area where the Store was located became known as ‘gamblers row’.   All the owners of the alternative establishments paid a percentage of their profits to McDonald.   The existence of these payments has been regarded by some as evidence of how McDonald was involved in the protection racket.  McDonald had criminal and shady activities besides gambling.   He might, though, have felt money from the other gambling establishments was owed to him because of his investment in the Store, an attraction that brought punters to the area.   Yet it does not require prejudice against McDonald to imagine his demands for a percentage being forceful and anything but generous.  McDonald was also a key player in a bookmaking syndicate which dominated gambling at the lucrative Garfield Race Track in Chicago and other tracks in Illinois and Indiana.   

More schemes followed.  McDonald formed shell companies and with the help of bribes and sweeteners he secured building contracts from the Chicago officials.  The Chicago newspapers were alert to these scams.   Such schemes attracted the derogatory term ‘boodling’.  The hostility of the newspapers could not prevent ‘boodling’ occurring.   His connections also enabled McDonald to put up bail for convicted criminals.  This made McDonald money in two ways.  He operated as a bail bondsman and, because of the money owed to him by the convicted, he accumulated credit and future funds.  In itself this would have been rewarding for McDonald but he was also a master of something called straw bail.  This involved judges awarding modest amounts for the convict to secure bail.   The criminals would often then disappear but at least the judges, the cops and McDonald  took a cut of the commission.  All these activities made him wealthy and influential.  And for insurance he managed the election campaigns of Mayor Carter Harrison, known to McDonald and his friends as ‘our Carter’.  

McDonald bought part ownership in the Chicago Globe.  The local press had not always been sympathetic to McDonald.  The Chicago Times wrote, ‘Mike McDonald is an unscrupulous, disreputable, vicious gambler, a disgrace and a menace to the city.’  The Chicago Globe lasted eight years before it folded in 1885.  Novelist Theodore Dreiser worked on the newspaper but not for eight years.  The likelihood is that the Chicago Globe did little to affect the reputation of McDonald.  If McDonald had been unlucky in 1861 when the Chicago Fire had destroyed his property, the Chicago World Fair boosted business in the city and the wealth of McDonald for the five months it lasted.  The 1893 Chicago World Fair is also known as the World’s Columbian Explosion.    

Neither of the two marriages of Michael Cassius McDonald was a success.  Both wives were much younger than McDonald and both dallied with other men.  His first wife Mary shot a policeman that she said had ‘invaded’ the hotel area of the Store.  Who knows what happened.  The only other important witness was dead.   An expensive defence lawyer ensured that Mary was acquitted.  McDonald celebrated the court victory by buying a new palatial home close to friend Mayor Carter Harrison.   Within a year of that happening, Mary had eloped with a noted minstrel singer.  McDonald chased the couple across the country and found them in San Francisco.   Mary pleaded to McDonald and urged him not to kill her lover.  The singing and plucking minstrel singer and his banjo survived.  Mary returned to her husband, and they lived together for another seven years but the couple were remote from each other.  Mary found solace in the Catholic faith and headed for a convent.   

Second wife Dora was a local burlesque dancer.  Dora and her husband had something in common.  They preferred their sexual partners to be much younger than they were.  Dora pursued a teenager called Webster Guerin.  There is confusion about how old Guerin was when he met Dora. Some authors quote his age as fifteen, others believe Guerin was no more than thirteen.  The affair between Dora and Webster lasted for ten years.  Dora shot and killed Webster during a heated argument.  When this happened McDonald had long been known as King Mike.   The behaviour of his two wives and his dependency made him appear foolish, pathetic rather than regal.  McDonald established a defence fund for Dora that cost him serious money but five months before the trial began old King Mike died.   Dora was acquitted.  The world and Chicago moved on.  A century turned and thanks to the camera and Hollywood the behaviour of the two wives inspired movies.  No prizes for guessing which.

Howard Jackson has had thirteen books published by Red Rattle Books including novels, short stories, travel books and collections of film criticism.  His latest book Long After This is now available here.