Chicago’s Original Crime Boss: Michael Cassius McDonald

May 9, 2013 - by Kelly Pucci - 0 Comments

May 9, 2012

 Michael Cassius McDonald

Long before Al Capone stormed into Chicago, a violent little Irish-American ruled the mean streets of Chicago.

by Kelly Pucci

Though long-forgotten by many, latecomers like Capone, Torrio and Colosimo owe a debt of gratitude to Michael Cassius McDonald, the man who brought togethercriminals and elected officials, setting the stage for organized crime in Chicago. During a 50-year career in the underworld, journalists, gangster, mayors and even one president of the United States took orders from Chicago original crime boss.

Michael Cassius McDonald arrived in Chicago just before the Civil War. A teen-aged runaway from Upstate New York, McDonald knew no one in Chicago. His childhood friend and fellow freight train jumper, Henry Marvin, died en route and was buried by McDonald without fanfare.

In the 1850s Chicago became the nation’s railroad hub opening the city to a flood of eager young men with big ideas. Young men like Marshall Field, who opened a retail emporium in downtown Chicago, and George Pullman, creator of the eponymous sleeping and dining cars that made travel by train comfortable and later carried President Abraham Lincoln’s body on a final journey from the White House to Springfield, Illinois.

But when Mike McDonald rode the rails in the 1850s, passengers sat on hard wooden benches as they stared at an unchanging landscape through sooty windows. With little to occupy bored passengers after consuming lunches brought from home, passengers eagerly welcomed the sight of boys called “candy butchers” who trudged through the aisles. In exchange for a few pennies and free transportation to Chicago, runaways and orphans clad in ragged clothing peddled goods for the railroad. Sympathetic passengers, mistakenly believing that the boys received their fair share of profits, bought poor quality goods from the candy butchers. And Michael Cassius McDonald was the most successful candy butcher of his time.

An Enterprising Lad

Slight in stature, he peddled books and fruit to kind-hearted ladies. Male passengers, duped by his innocent appearance, took candy home only to discover when opened by a loved one the boxes were half empty. Eager to increase his profits, McDonald expanded his business to include phony raffle tickets. Chicago crime writer Richard C. Lindberg credits McDonald with inventing the “prize package swindle.”As Lindberg explains it, McDonald guaranteed a cash prize of up to $5 in every box of candy purchased. Most prizes amounted to a few cents, but once hooked by the possibility of a big prize, greedy passengers tried and tried again leading McDonald to proclaim “There is a sucker born every minute” long before film star W.C. Field uttered the famous phrase.

Most boys tired of the grind, working long days for pennies and sleeping in dirty railroad yards at night. But McDonald, now in his late teens, wasn’t like most boys. He expanded his business. From wealthy passengers not afraid to gamble tidy sums of money, he learned to play cards. A keen observer of human behavior, McDonald watched their body language as they bluffed and wagered their way through intense poker games. Soon he exchanged his ragged clothes for the attire of a card sharp: a crisp suit, polished shoes and an ever present cigar. He continued to work days, but at night he joined floating card games in The Sands, Chicago’s vice district, going up against some of the best card sharps in the country.

Until the election of Mayor John Wentworth in 1857, Chicago officials unofficially tolerated The Sands, but within a few weeks of his first term, Mayor Wentworth declared war on The Sands. Literally overnight the mayor and his police force destroyed The Sands, burning to the ground or tearing down every shack, brothel and gambling parlor after issuing a 30-minute warning to occupants get out.

But Mike McDonald was not discouraged. He correctly predicted that gambling, no longer contained in one Chicago neighborhood, would spread throughout the city making the job of finding gamblers more difficult for police. In fact, the police force was so inept that Mayor Wentworth fired the entire department, until public pressure forced him to reverse his decision.

Discrimination against the Irish and Irish-Americans prohibited McDonald from applying for many honest jobs; elected officials enacted legislation to prohibit immigrants from holding city jobs.  But McDonald’s illegal business was flush with a customer base that included politicians, judges and city officials.

Gaming the System

McDonald operated Chicago’s most successful floating faro game, a European card game popularized in America by Wyatt Earp and Mississippi Riverboat gamblers. Played with a unique deck of cards laid out on an elaborately decorated card table with hidden compartments to allow dealers to skim money, players had little chance of winning. Occasionally McDonald instructed his dealers to adjust the game in favor of influential business leaders, but quipped “Never give a sucker an even break” – another phrase later popularized by W. C. Fields. Games often ended in violence but by this time local cops could be called upon to remove the angry patron in exchange for a bonus from McDonald’s men.

When President Abraham Lincoln called upon Illinois citizens to sign up for duty in the Union Army, McDonald did his best to aid the call to action. Though able-bodied, 22-year old Mike McDonald did not enlist in The Irish Brigade. Instead he organized groups of bounty jumpers. These men collected a $300 signing bonus called a bounty, and then deserted the army as soon as possible with money in hand and returned to Chicago to enlist under an assumed name. McDonald pocketed 50 percent in exchange for a promise of immunity from a crime punishable by hanging. Government officials desperate to fill quotas looked the other way as McDonald signed up Chicago’s drunken, derelict and destitute men. During the first two years of the Civil War, Illinois supplied more than 130,000 men to the Union army and McDonald accumulated enough money to purchase a saloon and adjoining gambling parlor in a luxury Chicago hotel.

Perhaps it was ready access to an unlimited supply of alcohol that fueled McDonald’s violent temper. On one occasion he punched and kicked a 60-year old woman who owned a roadhouse he frequented; he knocked down a man who tried to steal his handkerchief; he pummeled a man in a saloon and when the poor fellow tried to defend himself against McDonald the police hauled the man off to jail.

As the nation suffered through the Civil War, Chicago and Mike McDonald prospered. Businessmen in town to negotiate lucrative Union contracts, White southerners displaced by war and Confederate soldiers, escapees from a prison camp on Chicago’s south side, provided a steady stream of gamblers at McDonald’splace. Through his wealthy customers McDonald learned of skyrocketing land values caused by the demand for new factories and housing for workers and he invested heavily in real estate. By the end of the war, McDonald owned several buildings, four gambling clubs and a liquor distributorship.

His notoriety attracted women of a certain type: young and flashy. Isabella or Belle Jewel met Michael McDonald when she danced in the chorus line at a popular theater where John Wilkes Booth performed Shakespeare. Smitten by Belle’s beauty, McDonald quickly welcomed her into his circle of friends, introducing her as Mrs. McDonald though they never married. They dined in the finest restaurants and lived in an exclusive neighborhood. Whether it was physical abuse at McDonald’s hand, or his habitual drunkenness that drove Belle to leave him after seven years, she did so with a flair for the unexpected. The former chorus girl, no longer the belle of the ball, joined a St. Louis convent where she remained until her death in 1889.

The Great Chicago Fire

A few weeks after Belle’s sudden departure from Chicago, the Great Chicago Fire of 1871 destroyed most of Chicago and every personal possession, business and building McDonald owned. Chicago and Michael Cassius McDonald were ruined, but not for long.

Chicago began rebuilding almost immediately after the outgoing mayor honored hundreds of dead citizens by closing saloons for a period of one week.

By the end of the year McDonald married Mary Ann Noonan Goudy, a stunning 24-year-old divorcee and mother of two. She and her toddlers moved into the house McDonald had shared with Belle Jewel.

Thousands of laborers rushed to Chicago to build new houses for 300,000 citizens made homeless by the fire. For months, skilled tradesmen arrived at a busy railway station located in the heart of a red-light district where McDonald set up a shabby, but conveniently located gambling parlor. To outsmart competing gambling parlors in the area, McDonald hired well-dressed men to greet passengers as soon as they arrived. Yes, McDonald’s men knew where to get a hot meal and, incidentally an “honest” card game to pass the time while looking for employment.

McDonald’s business drew the attention of Chicago’s new mayor, Joseph Medill, co-owner of the Chicago Tribune; Mayor Medill tried to shut him down. Medill successfully lobbied the state legislature to increase penalties for owners of gambling parlors. He forced saloon owners to close on Sunday, the one day a week that laborers were free to enjoy a drink or two at their neighborhood tavern. He ordered his police superintendent to raid gambling parlors, when he was lax in carrying out his duties, the newspaper Medill owned published a list of known gambling parlors and their locations.

With the support of the liquor distributors association and the publisher of a competing newspaper, McDonald publicly opposed the mayor’s edict to close saloons on Sunday. For a while saloons remained opened, but owners dimmed the lights, locked the front door and admitted patrons through a side or back door.

Well aware that the police superintendent knew his men took bribes from gambling parlors including his, McDonald threatened to expose him. As a compromise, McDonald and others under his protection received advance notice of impending raids. For the benefit of the public, police officers removed gambling equipment they stored for pickup by the owners the following day. On occasion the police smashed furniture, but only well-worn or broken items chosen by the owner. If an employee or gambler was inexplicably arrested in the raids, McDonald posted bail.

Mayor Medill continued to put pressure on McDonald, but the king of gambling emerged victorious. The police superintendent and his successor were fired. Mayor Medill fled to Europe under the guise of seeking treatment for unnamed health issues. McDonald successfully offered his own candidate to replace Mayor Medill. With a new mayor in office, McDonald flourished. Upon McDonald’s request, Mayor Harvey Colvin repealed the law that banned the sale of alcohol on Sunday. Recognizing McDonald’s ability to get things done, Chicago’s gambling community clambered for McDonald’s support – the result, Chicago’s original crime syndicate. Flush with payoffs from politicians who paid McDonald hush money in connection with their own shady businesses and money contributed by small and big-time gamblers, McDonald opened the most notorious gambling house in America.

“The Store”

In September 1873 the beautifully crafted wooden doors of McDonald’s 24/7 department store of gambling, popularly known as “The Store” swung open to reveal the luxurious interior of a multi-story brick building: fine carpets, thick velvet drapes and gleaming mirrors. A cigar store that sold the finest imported cigars and a saloon stocked with the best wines available occupied the ground level. On the second floor, a staff of impeccably dressed men stood behind oak gambling tables, ready to greet well-heeled players. The Palace European Hotel, little more than a fancy rooming house, welcomed out-of-town gamblers on the third floor. No longer happy to occupy the home of her husband’s former lover, Mary and the kids lived together on the upper floor with McDonald as an occasional overnight guest.

McDonald extended credit to politicians who walked over from City Hall and to U.S. Senator James G. Fair. A frequent visitor from Nevada, Fair made millions from co-ownership of the Comstock Lode, the richest silver mine in the United States, and from a partnership in a California railroad, Fair couldn’t resist paying a visit to The Store when he changed trains in Chicago on his way to work in Washington, D.C. Sir Charles Russell, a member of the British Parliament, played poker at The Store. McDonald treated with generosity wives who complained their husbands gambled away the family rent money, refunding their losses and vowing to ban them from The Store. He contributed to charities. When someone asked McDonald for a contribution of $2 to help defray the cost of burying a fallen police officer, he quipped, “Here’s $10, bury five of them.”

Despite McDonald’s dislike of policemen, he kept some on his payroll. He brandished a pistol at a large political gathering, but officers on duty kept their distance. Police escorted drunken voters to a polling place set up at McDonald’s business where he offered naturalization papers and voter registration forms on the spot. During a drunken rage he broke the nose of a stranger who commented on a newspaper article unfavorable to McDonald and his supporters. The man filed criminal charges, but the case never made it to court. McDonald assaulted a newspaperman and threatened to cut off his ear. When arrested for attempted murder of a rival gambler, a police officer escorted him to jail in a special carriage and recommended to the judge McDonald be released on bail immediately. Of course, he was acquitted of all charges and that evening he held a banquet for judges, city officials and police officers.

For a time, members of the Chicago police force disregarded department orders to raid The Store. But occasionally policemen showed up unannounced. One evening a group of officers bounded into The Store and up the stairs to the family living quarters with a warrant to arrest McDonald. Mr. McDonald was not at home at the time but Mrs. McDonald was. She responded by firing two shots at the policemen. Charged with attempted murder, she was led to penitentiary where she stayed just until her husband hired an expensive lawyer named Alfred Trude and bribed a judge who released Mary before reprimanding the policemen for their unlawful raid of the McDonald family home.

Like her husband, Mary enjoyed keeping company with minor celebrities who performed in Chicago’s many theaters. She quickly fell in love with Billy Arlington, an African-American banjo player who lived with his wife Julia on Chicago’s South Side. Mary showered Arlington with gifts and even brazenly introduced him to her husband at a dinner party. When Billy had to leave Chicago for a performance in San Francisco, Mrs. McDonald followed. By the time they reached Denver, Mary declared her undying love for Billy Arlington in a letter she mailed home to her husband. Undeterred McDonald followed the couple to San Francisco where he threatened Billy and Mrs. McDonald with a loaded pistol.

McDonald forgave his wife for her indiscretion. He promised his wife a new home away from The Store and sealed the deal when he moved his family to a limestone mansion on a wide boulevard lined with homes of prominent Chicagoans including the mayor.

Mary promised to be faithful and for a while she was. Through her husband’s generous contributions to a local Catholic Church, she met Father Joseph Moysant. While church workers completed preparation of his living quarters at the church, Mary offered the priest a spare room, and often her own room, in the McDonald’s spacious mansion. On one occasion they took a secret trip out of town. They continued a clandestine affair undetected for two years until they decided to leave Chicago forever.

Like Belle Jewel, Mary left Chicago wearing a nun’s habit, but she had no intention of joining a convent. The lovers took a train to New York were they boarded a ship bound for Paris. This time it took McDonald two months to track her down. Under advice of his lawyer, Alfred Trude, the man who defended Mrs. McDonald against the attempted murder of a policeman, McDonald filed for a divorce. Shaken by his wife’s latest infidelity he lamented to a friend, “When you cannot trust your wife and your priest, whom can you trust?”

Though busy operating his gambling parlor, collecting protection money and distributing police bribes, McDonald ran some honest and some not quite honest enterprises. He bought the Chicago Globe newspaper, a rival to former Mayor Medill’s newspaper the Chicago Tribune. He commanded hustlers and pickpockets to stay clear of the area around the Columbian Exposition so as not to damage Chicago’s reputation while it hosted millions of fairgoers. At a private meeting in the White House he persuaded President Chester Arthur to pardon a colleague convicted in a Ponzi scheme. He financed construction of Chicago’s first elevated rail line. He operated a racetrack. He invested in a quarry that sold limestone to city contractors at inflated prices. He hired a crew to paint city hall with a special liquid guaranteed to render the crumbling building waterproof and fireproof, billing the City of Chicago $180,000 for a job estimated at $30,000. The special liquid turned out to be a worthless mixture of lime, lead and linseed oil.

McDonald was a busy man, but still a man, a man who loved women. At age 56 he married a 21- year old Jewish actress named Dora Feldman who he remembered from the times she and his son played together as schoolmates. Like McDonald, Dora was divorced and like his former wife the new Mrs. McDonald was attracted to artistic types. For a few years the couple was happy to host lavish dinner parties in the home McDonald purchased for Dora and to dine late at night in fine restaurants after the theater or opera. But McDonald was getting older and slowing down. While he spent his afternoons napping, Dora sneaked away to meet her teenaged lover, Webster Guerin. Guerin couldn’t support himself by selling his paintings so Dora set him up in a picture-framing business downtown. Whether or not McDonald suspected his wife of carrying on a long-term affair, he continued to love his wife, even to the point of converting to Judaism and not questioning how she spent his money.

When Dora suspected that Webster Guerin was seeing another woman, who in fact was his brother’s girlfriend, she became enraged. She threatened to kill the woman. She threatened to kill Guerin. On a cold February morning Dora burst into her lover’s office and shot him dead in full view of witnesses. Though she admitted to the police she killed her lover, she told her husband that she killed the man because she was blackmailing her. McDonald paid for her defense, a team of prominent lawyers led by Alfred Trude, the man who defended his first wife against a charge of attempted murder.

The scandal took a toll on McDonald and he did not live to see his wife acquitted of murder. Michael Cassius McDonald died with his former wife, Mary, at his side and $2 million in assets.

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