Stranger Than Fiction

March 2018

Murder and Mayhem in the Windy City

By Dean Jobb

He was Chicago’s undisputed underworld boss. “A despicable wretch” and “a protector of criminals,” one of the city’s newspapers complained, “to be feared for his dangerous powers and to be despised for this brutality, cowardice and braggadocio.”

It sounds like a description of Al Capone, the most infamous crime figure in Chicago’s history and one of the most recognizable crooks of all time. But the Chicago Herald’s attack on this “little god among the thieves, safe blowers, garroters and crooked classes” was published in 1882, seventeen years before Alphonse Gabriel Capone was born. The target of the paper’s wrath was Michael McDonald, a son of Irish immigrants known as “King Mike” who built a gambling empire and dominated Chicago crime and politics in the Gilded Age. His successor, King Capone, was yet to be crowned.

Chicago is the setting for five recent true-crime books that look beyond Capone to explore the roots of the city’s long and bloody history of murder, corruption, and gangland violence—with a miscarriage of justice and a notorious serial killer thrown in for good measure.

The-Gambler-KingMcDonald emerges from Capone’s shadow in The Gambler King of Clark Street: Michael C. McDonald and the Rise of Chicago’s Democratic Machine (Southern Illinois University Press), by Richard C. Lindberg, recently reissued in paperback and the first full-length biography of this powerful, forgotten figure.

Operating out of a downtown gaming house known as “The Store,” McDonald bribed and corrupted police officers, court officials, and politicians as he built a Chicago version of New York’s Tammany Hall. A major player in the Democratic Party for more than two decades, he provided the money and muscle needed to fix elections and defeat law-and-order reformers. He helped put three mayors in office and his influence reached all the way to the White House.

Lindberg, a prolific author and an expert on crime and policing in Chicago, credits McDonald as “the first to integrate the ‘rackets’ into the electoral and legislative process, and thus influence the governance of Chicago.” Capone, a latecomer, merely adapted the template to the Prohibition Era.



Lindberg takes a wider view in Gangland Chicago: Criminality and Lawlessness in the Windy City (Rowman & Littlefield), an ambitious book that chronicles Chicago’s underworld from its Civil War-era origins to the late 1980s. Capone and McDonald make appearances, along with lesser-known thugs and gangsters with colorful nicknames such as “Klondike” O’Donnell and “Ammunition” Eddie Wheed.

Gangland Chicago presents a dizzying cast of characters, making it difficult at times to keep track of all the bad guys. But the steady stream of names and crimes reinforce how poverty, hopelessness, and prejudice have driven generations of young men into a life of crime, making them willing recruits for underworld leaders. Gangs are “the by-product of intense ethnic rivalries, tribalism, residential squalor, and economic hardship,” Lindberg writes.  Redevelopment and expressways have swept away the West Side “Terror District” and other notorious neighborhoods, but the scourge of gang violence endures.

Lindberg’s deep research and thorough knowledge of Chicago’s underworld are on display in both books, making them essential reading for anyone delving into the city’s dark past or seeking insights into its present-day struggles with crime.


Al-Capones-Beer-WarsJohn J. Binder brings a revisionist eye and more than two decades of research to an authoritative new history of the Prohibition Era in Chicago. Al Capone’s Beer Wars: A Complete History of Organized Crime in Chicago During Prohibition (Prometheus Books) takes a closer look at the dozen gangs that battled Capone—and each other—for underworld dominance in the 1920s.

“Prohibition was the single most important event in the history of organized crime in the United States,” notes Binder, a former professor of finance at the University of Illinois. With legitimate brewers and distillers forced out of business and people as thirsty as ever for booze, “gangland filled the void.”

Nowhere were the results as violent and bloody as in Chicago. Prohibition “looked like a good opening for a lot of smart young men,” Capone once noted. Many of these young men came to untimely ends as gangs fought to defend or expand their turf. And it proved to be a golden opportunity for Capone, the most calculating and ruthless gangster of them all.

Binder reviews the hits and takeovers, pausing often to correct the historical record with insights gleaned from his painstaking research and interviews with descendants of gang members. Among the myths refuted are surprising claims that Capone was merely a frontman for other gang leaders.

A trove of photos Binder has collected over the years—snaps from weddings and other family events as well as police mug shots—illustrate the book, bringing a rogue’s gallery of characters to life. “There is no full history of Prohibition Era organized crime in and around Chicago,” he notes, but Al Capone’s Beer Wars stands as the most definitive account to date.


Ugly-PreyCapone’s hitmen and Mike McDonald’s minions rarely saw the inside of a courtroom. But when Sabella Nitti’s abusive husband went missing in 1922, lurid rumors of adultery, a vindictive sheriff’s deputy, and a biased justice system combined to convict her of murder. In Ugly Prey: An Innocent Woman and the Death Sentence That Scandalized Jazz Age Chicago (Chicago Review Press), first-time Chicago author Emilie Le Beau Lucchesi tackles this forgotten tale of intolerance and injustice.

Nitti’s only crimes were being unattractive and a foreigner. She was poor, could not speak English, and appeared in court unkempt and clad in her farmwife’s clothes. Chicago Daily Tribune reporter Genevieve Forbes, in an attack that was cruel and abusive even for the sensational journalism standards of the time, demonized her as a “dumb, crouching, animal-like peasant.” A day passed before anyone bothered to send a translator to her cell with the news she had been sentenced to hang.

Lucchesi’s writing is lean and vivid as she recreates Nitti’s trial as well as the legal and social issues it put in the spotlight. She mines transcripts and newspaper reports for dialogue that injects life into courtroom scenes and jailhouse encounters. And she captures the drama and uncertainty as Nitti’s supporters battle to save her life. The book opens with her conviction and death sentence, but readers are kept guessing. Will she hang? Or will this gross miscarriage of justice be corrected before it’s too late?


H-H-HolmesSabella Nitti was convicted of a murder she didn’t commit. H.H. Holmes, in contrast, confessed to killing more than two dozen people and has been suspected of murdering as many as 200. But Adam Selzer, a Chicago blogger and tour guide, argues that sensation-seeking journalists and inept police investigations inflated the reputation of one of America’s earliest and most infamous serial killers.

Holmes, whose real name was Herman Webster Mudgett, is the “devil” in Erik Larson’s bestselling nonfiction classic The Devil in the White City. He was reputed to have lured young women and other visitors attending the 1893 Chicago world’s fair to his hotel—later dubbed the “Murder Castle”—and to their deaths.

For his book H.H. Holmes: The True History of the White City Devil (Skyhorse Publishing), Selzer scoured newspaper reports and unearthed firsthand accounts and court files to separate fiction from fact. “Many of the most common tales about him,” he discovered, “simply grew out of idle gossip in newspapers and police propagating theories that would be promptly dismissed as nonsense.” Holmes, a pathological liar who was paid handsomely to tell his story to the Hearst newspaper chain, gave the public the monster it wanted.

Selzer traces today’s image of Holmes as a sadistic psychopath who tortured his victims in a basement laboratory, and disposed of the bodies in acid vats or sold the skeletons as medical exhibits, to a handful of embellished and fictionalized accounts that were passed off as fact. One of the most influential appeared in journalist Herbert Asbury’s 1940s chronicle of Chicago’s underworld.

Holmes was executed in 1896 after being convicted of murdering just one person—a fellow fraud artist—and undoubtedly killed three of the man’s children. Selzer believes he killed five women in Chicago before and during the world’s fair, but remains sceptical about twenty-seven other victims identified in newspaper reports or by Holmes himself. He debunks another twenty-two suspected murders, noting that in one instance the purported victim was still alive in the 1930s.

The bottom line? “Holmes almost certainly killed at least nine people, ruined the lives of numerous others, and seemed to feel very little guilt about it,” Selzer writes. No more guilt, perhaps, than Al Capone or Mike McDonald felt as they staked out their own places in the history of Chicago crime.


Dean Jobb is the author of Empire of Deception (Algonquin Books), the true story of 1920s Chicago swindler Leo Koretz. His next book recreates the crimes of Thomas Neill Cream, a Victorian-era doctor who murdered at least ten people in Canada, Chicago and London. His website is

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