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Frequently Asked Questions

About the Chicago Prohibition Gangster Tour

The Gangster Tour

What does the Chicago Prohibition Gangster Tour cover?

Geographically, the bus travels from 3 miles south of the center of downtown Chicago to 3 miles north of downtown, all within about a mile of the lakefront. There are eight stops at points of historical significance related to Prohibition Era gangland. At three of these stops, depending on the weather and other factors, we leave the bus for a few minutes to have a closer look at the location and learn more about what happened there.

In terms of the subject matter, the tour is a deep immersion into the history of Chicago’s Prohibition Era gangs and gangsters. The major gangs, the conflicts between them, the careers of their leaders — such as Jim Colosimo, John Torrio, Al Capone, and Hymie Weiss — and the gangs’ revenue-generating activities (such as bootlegging, prostitution, gambling, narcotics, and labor racketeering) are discussed in detail.

What basic things should I know about the tour?

You ride on a luxury coach bus. As mentioned above, we leave the bus at three points to explore certain details. That is, of course, if stepping off the bus works for the people on the tour that day. No other walking is required.

Who is the guide on the Chicago Gangster tour?

John Binder guides each and every tour. He is the author of two well-received books on organized crime in Chicago: The Chicago Outfit (Arcadia Publishing, 2003) and Al Capone’s Beer Wars (Prometheus Books, 2017). John was also the president and a member of the board of directors of the Merry Gangsters Literary Society. He has been a consultant to the Vegas Mob Museum, the Chicago Historical Society, and has appeared on a number of documentaries dealing with the history of organized crime. He is frequently contacted by other authors and researchers for help on their books and projects. It is fair to say that your guide is an expert on this subject, and he is happy to answer your questions about this part of the history of Chicago or the evolution of organized crime after Prohibition.

Mug shots of Al Capone

Alphonse Capone

What was Al Capone really like?

In his private life, he was a doting father, but not a very faithful husband. On a personal level, he could be friendly and outgoing, and I believe that personally he liked to be liked. As a gangster, he killed people and ordered them killed. He was effective (in his chosen profession) as a gang leader because he could be ruthless when necessary but also diplomatic when it was in his interest, even with former enemies. He was a good “general” in the gangland sense, but he was also a good businessman, which cannot be said of every Prohibition Era gang leader.

Was Al Capone the most powerful man in Chicago, with complete control of the city?

No, not by a long shot. At his height, he had 500 gunmen in his gang. The mayor of Chicago had some 6,000 regular police officers available to him, backed by auxiliary police, the National Guard in times of emergency, and the entire U.S. Army, if necessary. Capone never pushed the mayor of Chicago around.

Did Capone control the bootlegging in all of Chicago?

No, he was never that powerful in the underworld. In 1924, there were 12 major bootlegging gangs in the city. In 1932, after Al Capone was in jail, there were still 11 major bootlegging gangs in Chicago. Even Capone’s successor, Frank Nitti, never controlled all of the bootlegging; there were other gangs in Chicago right up to the end of Prohibition (1933).

Why did Capone go to prison?

Al Capone was ultimately convicted not for murder or bootleging, but for income tax evasion. A squad of IRS agents built the case against him after an extremely thorough investigation; the case went to court, and the government won. Capone got a 10-year sentence for income tax evasion.

Did Capone die in prison?

Only in a movie. In real life, he was paroled from Alcatraz in 1939 because he had an advanced case of syphilis, and he eventually died in Florida in 1947.

George "Bugs" Moran and the St. Valentine's Day Massacre

Was the North Side Gang, ultimately lead by George Moran, wiped out in the St. Valentine’s Day Massacre (SVDM)? Did it only have seven members in 1929?

That’s one of the biggest myths in this area of history. The North Side gang had probably 200 gunmen in 1929 who had been members for a number of years, plus the men working for Moran’s major allies, who merged with his gang in 1927.

What exactly happened on St. Valentine’s Day, February 14, 1929?

Five prominent members of the North Side gang, a mechanic, and a hanger-on were executed in a garage on Clark Street by gunmen posing as police officers. Six of the men died immediately, and the seventh died that afternoon in a hospital. The garage was used by a section of the North Side gang as a headquarters. The main target, George “Bugs” Moran, was not there that morning. He was actually walking toward the garage, but when he spotted what looked like a police raid, he simply turned around and walked back the way he had come to his hotel.

When did George Moran lose control of the North Side area in Chicago?

Not until August 1930, a full 18 months after SVDM. And the gang wars, or Beer Wars as they are often referred to, continued on until the end of Prohibition — the Capone gang and others were still fighting with their enemies in the early 1930s.

Is it true that Al Capone had nothing to do with the St. Valentine’s Day Massacre?

Recently, there have been claims that a felon known as “Three Fingered Jack” White planned and committed the Massacre on February 14, 1929. Simply put, the major problems with this assertion are: 1) White was in jail from early 1926 to the middle of 1929, well after the massacre occurred, and 2) he had no motive to do it. There is a large body of evidence that shows that Fred “Killer” Burke and a crew of gunmen under his direction did it, hired by Al Capone and his allies. This evidence includes three eyewitnesses who saw Burke enter the garage at 2122 N. Clark Street the morning of the massacre, papers found in the office of Capone gang ally Claude Maddox which showed that he had brought the gunmen in to do the job, and the confession (to the FBI) of one of the lookouts working with Burke’s crew.

Chicago Gangsters standing by a car

Prohibition, Bootlegging, and Gangland Violence in Chicago

Where did the beer and hard liquor come from during Prohibition?

The beer was brewed close to home. Depending on the circumstances, that was in Chicago itself, in the surrounding areas, or in lower Wisconsin. Quality hard liquor came in many cases from other countries like Canada, Scotland, Ireland, and those in the Caribbean. Massive amounts of pure alcohol were distilled in the Chicago area during Prohibition, and by adding water, flavoring, and food coloring to it, lower-quality substitutes for whiskey, Scotch, and more could be concocted.

Were there any “good guys” in Chicago during Prohibition?

Yes, quite a few, in fact. Reform mayor William Dever (1923 – 1927) told the Chicago Police Department to enforce all laws, whether they were popular or not. This hit organized crime very hard. Some high-ranking CPD officers and many men in the Detective Bureau were incorruptible. Obviously, federal agents with the IRS and the special squad of Prohibition agents led by Eliot Ness were honest. There were also various citizens’ groups, including the Chicago Crime Commission, the Juvenile Protective Association, and later the group known as the “Secret Six,” which fought organized crime in Chicago.

Did organized crime in Chicago/the United States start during Prohibition?

No, there was active organized crime in Chicago and in most major cities decades before 1920. This includes gambling and prostitution in Chicago going back to before 1850, and by the 1890s there was labor racketeering as well.

How violent was gangland in Chicago during Prohibition?

The underworld violence here was the worst of any American city, partly because at one time there was virtually a city-wide gang war among the various bootlegging mobs. According to the CCC, there were 729 gangland-style killings in Chicago from 1919 to 1933. However, many of these were unrelated to bootlegging or organized crime in general, and in the bootlegging-related murders the victims were often not members of the major bootlegging gangs. Only about 140 of the 729 victims belonged to the various bootlegging gangs. So the gang wars in Chicago during Prohibition were a lot less violent than had long been believed. A lot of “independents,” who thought they could operate in the areas controlled by the established gangs or who hijacked liquor trucks owned by the major bootlegging gangs, were killed.

Did the gangsters have stand-up gun battles during Prohibition where both sides blazed away at each other?

That sort of thing almost never happened. In fact (as opposed to in movies), most of those 729 killings documented by the CCC were executions where usually one or two victims were caught off guard by their enemies. The victims very rarely returned fire, much less killed any of their attackers. For example, there is only one incident in Chicago (or anywhere else that I know about) where rival bootleggers shot at each other with machine guns, and in that case no one was killed!

Did the gangsters generally use submachine guns when trying to kill their enemies?

No, the Thompson submachine gun was rarely used in gangland, even in Chicago where it was probably used more frequently during the Dry Era than anywhere else. Hollywood’s love affair with the submachine gun has created the impression that it was far and away the weapon of choice. The Prohibition Era gangsters used pistols and shotguns heavily, just like their predecessors in the underworld and the peace officers and gunmen in the Old West.

Is it true that the gangsters only killed each other?

That’s a little fantasy that the hoodlums like to spread. They have killed lots of non-gangsters over the years, such as ordinary individuals who would not knuckle under to them, labor union leaders who resisted their inroads, witnesses against them, and even members of law enforcement.

When did Chicago become world-famous for its organized crime? And why was that true about Chicago versus another American city?

Chicago was already known around the world in this respect during the 1920s. You had fascinating characters — such as Al Capone, who was internationally famous, and “Bugs” Moran — some of whom actually talked to reporters and were quoted in the newspapers. You had lots of related violence, some of it very spectacular, like the St. Valentine’s Day Massacre, and at one time virtually a city-wide gang war. Over the years, Hollywood has reinforced that by setting many gangster movies in Chicago.

Were all the bootleggers during Prohibition and the members of the Chicago Outfit after Prohibition of Italian ancestry?

No, many of the bootleggers during the Dry Era were, for example, Irish, German, Jewish, Czech, or Polish. In fact, there was a very broad mix of ethnic groups in Chicago involved in bootlegging at the time. This was true even in Capone’s gang, which became the Chicago Outfit after Prohibition. The Chicago Outfit has had many members over the years, some quite high ranking, who were not Italian. The major exception to this is that there are no known cases of African-Americans being involved in bootlegging in Chicago during Prohibition or who were full members of the Outfit. On the East Coast and elsewhere, there were also many non-Italian gangsters during the Dry Era. After that period, most Cosa Nostra crime families have had rules (barring certain exceptions) that only those of Italian descent could be full members.

Al Capone smoking a cigar

Eliot Ness

Who Was Eliot Ness?

Ness was a real-life Prohibition agent. He was honest and led a squad known as the Untouchables. His raids on Capone’s breweries and distilleries were the basis for a federal indictment of Al Capone and other members of his gang for bootlegging. However, the government went forward with the income tax case against Capone, and it did not pursue the bootlegging case any further after he was convicted of tax evasion. However, like many bureaucrats, Ness was a self-promoter and took newsmen along on raids with him, which was problematic.

In movies and on television, Eliot Ness is always face to face with Al Capone. Did they ever meet?

Ness went to Capone’s tax trial, but he was a mere observer there. But when Capone was transported from jail to the train that took him from Chicago to the USP Atlanta in 1932, Ness and a couple of the Untouchables were part of the guard detail that night. So he was only a few feet, at most, from Capone at that time. Whether they spoke, we don’t know for sure — but probably not because Ness would surely have mentioned it in his autobiography.

Did Eliot Ness throw Frank Nitti off of a roof?

No, that is Hollywood stuff from The Untouchables movie with Kevin Costner. That movie is very historically inaccurate. Nitti succeeded Capone as boss of the old Capone gang in 1932, and he created the Chicago Outfit from it. He died in 1943. Furthermore, Ness did not dry up Chicago or do many things that he is shown doing in movies or on television.

Train tracks running through Chicago

Other Questions

Did the Chicago Mob or, more broadly, the Cosa Nostra in the U.S. have a no drugs rule?

Nothing could be further from the truth. The Capone mob was active in illegal narcotics back in the 1920s, and the Chicago Outfit has been involved in that for years. So have the other major Cosa Nostra crime families in this country. Simply put, they will do whatever they think they can reasonably get away with if it will make them money. And there is quite a bit of money that they can make in the drug trade. For self-esteem and other reasons, they don’t like to admit that they are involved with illegal drugs.

Is the objective of organized crime to kill people or to achieve political power?

No. The sole goal of organized crime, just like ordinary crime (burglary, robbery, etc.), is to enrich the perpetrators. Corruption and violence, or the threat of violence, are means to that end, but they are secondary to the objective of making money.

What is your favorite mob movie?

Well, that’s a matter of personal taste. Some are fairly factual. Others are highly entertaining and even cinematic masterpieces, even though they stray from the facts. In the latter group, movies like Godfather I and II, The Untouchables, Once upon a Time in America, and many others come to mind.

Which mob movies are the most realistic?

In terms of the Prohibition Era, probably The St. Valentine’s Day Massacre, directed by Roger Corman. Post-Prohibition, hands down it would be Goodfellas.

Why is John Dillinger included on the tour?

Technically, I would label Dillinger a bank robber or outlaw, not a gangster, because the latter term is best used to describe people in the world of organized crime. However, since Dillinger was nice enough to get himself killed in Chicago in 1934, the tour visits the Biograph Theater, where he was shot by federal agents.

Some Recommended Readings


John J. Binder. 2017. Al Capone’s Beer Wars (Prometheus).
Available for purchase on the tour or on the internet.

Rose Keefe. 2005. The Man Who Got Away: The Bugs Moran Story (Cumberland House).

Rose Keefe. 2003. Guns and Roses: The Untold Story of Dean O’Baanion. Chicago’s Big Shot Before Al Capone (Cumberland House).

Robert Schoenberg. 1992. Mr. Capone (Morrow).

John Kobler. 1971. Capone (Putnam).

Before Prohibition

Herbert Asbury. 1942. Gem of the Prairie (Garden City).

Virgil Peterson. 1952. Barbarians in Our Midst (Atlantic).
This book also covers the era after Prohibition.


After Prohibition

John J. Binder. 2003. The Chicago Outfit (Arcadia).
Available for purchase on the tour or on the internet.

Mars Eghigian. 2006. After Capone (Cumberland House).

Ovid Demaris. 1969. Captive City (Lyle Stuart).



Helpful Resources

Mario Gomes’s My Al Capone Museum

Rose Keefe’s author page