Gem of the Prairie: An Informal History of the Chicago Underworld

by Herbert Asbury

This classic history of crime tells how Chicago's underworld earned and kept its reputation.

Genres: History, True Crime, Nonfiction, Crime, American History, Historical, American

377 pages, Paperback

First published January 1, 1940

About the author

Herbert Asbury (September 1, 1889 – February 24, 1963) was an American journalist and writer best known for his books detailing crime during the 19th and early-20th centuries, such as Gem of the Prairie: An Informal History of the Chicago Underworld, The Barbary Coast: An Informal History of the San Francisco Underworld and The Gangs of New York.

Reviews

[Mark Russell · Rating 5 out of 5]

A highly engrossing, if apocryphal, account of the history of crime in Chicago dating from the early small town days when defendants were tried in a carpentry shop to Capone, the Valentine's Day Massacre and the heyday of Chicago's gangland era.

Among the many wonderful anecdotes in Gangs of Chicago are the story of a 400lb madam who eluded capture by the police simply by being too large to exit the doors of her brothel and a dedicated policeman who, because of his miniature size, forced arrestees to give him a piggyback ride to the police station.

While a lot of the stories seem too good to be true (and that's not a bad thing), taken in composite, you still get a pretty good sense of what the streets of Chicago were like during much of the 19th century. On Cheyenne Street alone (the city of Cheyenne retaliated by naming its red light district after Chicago) there were over a hundred houses of prostitution and gambling, many of which were in buildings owned by aldermen and high ranking police officers, which pimps and madams cleverly rented in hopes of preventing police raids.

Most brothels were often little more than mugging stalls, the most notorious being the infamous panel houses where an unsuspecting john would leave his pants, jacket and shirt on a chair against the wall only to find afterward that someone had opened a secret panel in the wall and had stolen his wallet, his watch, his clothes and all. The prostitutes themselves hardly fared any better in the trade. Many were lured to Chicago by handsome young men known as "procurers" with promises of factory work or marriage, only to be handed over into white slavery once they arrived. After being forcibly inducted into the life of a prostitute, many were simply too ashamed to ever go home again.

Asbury's anecdotes are mostly compiled from old newspaper reports, oral accounts and local legend, so it's not exactly the most authoritative source material, but his enthusiasm is infectious and he effectively captures the spirit, if not always the letter-perfect reality, of Chicago's transition from an adolescent boom town to a respectable metropolis.

[Kris · Rating 2 out of 5]

Not sure why all the previous reviews have higher ratings, as this was a very poorly written book. Where was the editor?? Parts of it read normally but other parts are determined to just jam paragraphs full of facts that become meaningless after a while. It also tends to repeat itself and skip back-and-forth in a way that makes you want to just stop reading. Funny how a book about such decadence can be so dull. However my love for Chicago history prevailed and I did make it through. It seemed like the ending chapters with Capone were written better, I almost wonder if he had a ghost writer for parts of this. However, all in all this book needed serious editing and I don't think I'll ever read anything else he wrote.

[Kaesa · Rating 1 out of 5]

Oh my god, this book was incredibly dated and full of suspect information. I'm really glad I read it, because I have secured some VITAL information for a historical story I'm writing (which may not be strictly true but it gives me something to build on), and that's the only reason this thing is 2 stars instead of 1. I almost DNF'd it.

[EDIT: no, fuck it, one star. The book is too vicious to get the second.]

I think one of the two main problems was that the author kept credulously repeating things people told the newspapers as fact. Having read old newspapers from some of the eras this is written about? No, absolutely not, you have to be skeptical of that. Among other things he retold the story of Mrs. O'Leary's cow and then basically said "but some people think that might not be true. Who knows???"

The other main problem was incredible racism and sexism, which I have spoiler cut because I go on for several paragraphs about some pretty unpleasant things relating to historical sex work, racism, kidnapping, sexual slavery, rape, and child sexual abuse. It gets... pretty bad. I would have been really interested in a book that covered these topics more sensitively, or at least more informatively; neither would be a high bar. In a paragraph singing the praises of how extremely smart and classy Johnny Torrio was, we get this: "He neither smoked nor drank, he was never heard to utter a profane or obscene word, and as far as he was concerned, the women who filled his bordellos were just so many articles of merchandise." (emphasis mine) This isn't an isolated thing; I sighed heavily because after having read the two and a half previous chapters heavily covering the sex trade in historical Chicago, Mr. Asbury appeared to be incapable of thinking of anything worse than a hooker, except perhaps a hooker who wasn't white. He constantly segues into describing women's bodies in the most monstrous, freakish of terms, especially Black women. Without using any actual slurs, he was at a couple points so vicious and unpleasant in one of his descriptions of a group of Black women that I was uncomfortable typing up his descriptions when chatting with friends about the book. A couple pages later, there were photos of the women in question. I don't think anyone deserves to be so completely dehumanized, but even if, somehow, one could deserve that just for one's appearance? These women did not. They looked completely normal. I would not have done a doubletake passing them on the street, but for the very snazzy Victorian hat one was wearing. I don't expect enormously sympathetic portrayals of any criminals in a book published in 1940 but it felt egregious, especially as I was reading Nelson Algren's The Man With the Golden Arm at the same time -- published only eight years later in real time and about a thousand times more compassionate towards people who are just trying to get by.

There is also, horribly, a very credulous acceptance that one brothel kept on hand six large Black men for the sole purpose of raping little white girls to "break them in" before selling them. The author doesn't cite his sources; I assume a newspaper, as an illustration from the newspaper of two of these little white girls heroically escaping from the brothel by climbing down tied-together bedsheets is on the next page. This seems genuinely ridiculous to me; it sounds like something the paper might have made up, that audiences of the time would not need much evidence to believe. There's a lot of reference to brothels' practice of having kidnapped women and girls raped to "break them in" and trap them into a life of prostitution, and this is sadly plausible to me given the sexism of the era, but being violently raped by six people in quick succession seems likely to seriously injure a grown woman, much less the 12- and 13-year-olds being discussed. Since the girls were then supposedly sold off to private buyers, who would presumably want to use (ugh) their purchase sooner rather than later, and have her live, I cannot imagine such a practice being profitable. It is a story designed to sell newspapers to people who love to be horrified, and who are predisposed to think Black men are subhuman rapists. It is the distant, disgusting cousin of rumors that drug dealers are trying to get your children hooked on their products by giving out free heroin-laced candy on Halloween. It's fucking absurd.

There is, I think, a story here about the sex trade in Chicago getting crueler as it moved out of the sight of the general public and into suburban bordellos owned by a couple rich mob bosses -- the women seem to have less choices, less alternatives, are more often kidnapped children and not women at all. But Asbury doesn't seem to have noticed that aspect; instead he prefers to concentrate on avoiding repeating himself, and calls prostitutes "harpies," "strumpets," and "harlots" all on the same page.

The history of sex work in Chicago isn't something I know a ton about, so I could be wrong about a lot of this, but various little details kept leaping out at me and I wanted to know more about, say, the reformers who, instead of physically driving prostitutes out of the vice district, decided to help department-store employees (mostly female and extremely poor) agitate for better pay and more rights. But he mentions it once and then spends pages and pages on the noble destruction of the vice district. And where did the prostitutes go once that vice district was forcibly shut down? He doesn't really say. It's reminiscent of the way a lot of my wealthier neighbors talk about how nice it is when the cops drive homeless people out of the underpasses and confiscate their tents in the dead of winter. The ones who don't die must go somewhere, but what's important is the appearances and high property values. Call it a pet peeve but that kind of total lack of compassion drives me crazy. This book is full of something, but there isn't an ounce of compassion except for, weirdly, Jimmy Torrio. (I don't know what the author's deal was with that. Again, it feels like an admiration of superficial respectability.)

tl;dr I'm thrilled I got some material for some fiction I've been working on, information that I've been looking for all over and not finding, but I'm genuinely sad that I have to keep this book for reference until the story is finished, because fuck this book.

[Heather Lisson · Rating 4 out of 5]

Great chronicle of Chicago from its growth out of the swamps through the 1920s. Interesting depiction of the development of crime, the inadequate police force, the political corruption, and the reformers who fought to stop the sin that the city had become. I lived in Chicago for a year and it is still the same city in a lot of ways; full of ploys, vices, and peril.

[Rhuff · Rating 4 out of 5]

Originally titled "Gem of the Prairie," this was a followup to the better-known "Gangs of New York." Herbert Asbury was the go-to authority on the American urban underworld of the late 19th-early 20th century. This volume demonstrated Chicago, as both commercial and criminal capital, to be on par with its eastern rival.

Here Asbury details the lowlife doings from the Great Fire to Prohibition. Readers may be surprised to learn that Al Capone and the Italians were latecomers to the city's criminal counterculture. We encounter panel houses and madams, heistmen (and women), Black Hand bombers and the Shot Gun Man, corrupt aldermen and the crusaders who fought them. The most egregious character was Henry Holmes, the serial killer "Monster of 63rd Street," who turned his "castle" into a miniature Auschwitz with its own crematoria. Here, perhaps, we sail into newspaper-fed sensationalism, for it's really hard to believe he got away with so much for so long, from Texas train robber to Chicago mass murderer, before his reckoning.

Yet some matters of concern to Chicago's police and crusaders are noticeably absent. There is no mention of the period's most sensational murder case of Dr. Patrick Henry Cronin, by fellow Irish nationalists; of the earlier "Dynamite Convention" of Clan-na-Gael; nor the police paranoia over the anarchist movement and the Haymarket explosion. Asbury's focus is strictly on "vice," as defined by the Victorian morals of the era, not politics, and this might be understandable: criminal gangs were so embedded with the police that dumping on "reds" was a good cover for both. Yet it was a serious hole in the fabric of law and order in early Chicago.

Written as popular history and entertainment, Asbury's works offer a glimpse into the maggoty underside of gaslight and low-watt America, of things that those in "the city on a hill" would prefer not to know. Rest assured this volume will soon disappear from Florida libraries.

[Richard · Rating 4 out of 5]

Much like The Gangs of New York, Asbury offers a history that is perhaps a little more the reportage of legend than hard-driving investigative journalism...though just as easily, Asbury's work makes one wonder whether there has ever really been those distinctive lines even in journalism. The cast of characters, the language of the time, are all pleasures to read, and one can see here just as much as with NY how Scorsese's movie version took hold with this kind of material. Don't read this book to be able to become an expert but to savor the flavor of the underworld gone by.

[Mary · Rating 3 out of 5]

It’s a fun read and shouldn’t have taken me quite this long to complete.

If you are interested in Chicago history and some of the players of the 19th and early 20th century start here. Then read some serious works. For example the author reinforces many of the myths about HH Holmes ghat have been promoted over time but after comparing that section to Adam Selzer’s work one sees many discrepancies.

Overall a pleasant but somewhat sensationalist look at my hometown.

[STEPHEN MACPHERSON · Rating 4 out of 5]

Very similar to The Gangs of New York- a quick overview of almost (at the time of publication) 140 years of Chicago's infamy. A good book to branch off of- Karen Abbott's Sin in the Second City and Jonathan Carr's historical fiction Make Me a City give a little more detail.

[Brittani Jolley · Rating 3 out of 5]

The book isn't told like a traditional story. It jumps around based on events rather than timelines.

[Julie Pryst · Rating 2 out of 5]

Eh...

[Dory Drummond · Rating 3 out of 5]

Very dry. Has some interesting facts and figures. Do not recommend. Did not read whole book.

[Carly · Rating 4 out of 5]

A great look into the 19th/20th century Chicago underworld. We all know the story of Al Capone's Chicago, but this book mostly focuses on the pre Capone Chicago of the 1800s and early 1900s.

[Aaron · Rating 3 out of 5]

When I picked this one up I was itching for an interesting book highlighting the mobster and gangland scene of Chicago. What I got was a comprehensive history of how the Chicago underworld progressed since Chicago made the transition from frontier town to a booming hub of the US. This means there was a huge portion of the book devoted to less interesting (IMO)facets of crime such as gambling, pickpocketing and brothels. Through the first 2/3 of this book, I appreciated seeing the factors and circumstances that gave birth to an underworld that feasted on the rapid growth of Chicago. However, my mind was numb from the hundreds of names of seemingly meaningless criminals the author felt obligated to mention. Once the book reached the turn of the century and the gangster era was looming, I found myself much more interested in the book. The last third of the book flew by while reading about the likes of Johnny Torrio, Al Capone, Dion Obannion, Bugs Moran, etc. However, since the book was published in 1940, I feel a lot of the mobster history was incomplete; leaving me feeling unsatisfied. It made me wish I would have just found a book more focused on the gang wars epoch of Chicago. The exhaustive examination of the Chicago underworld from the start gave a great background, but a more summarized lead-up would have been preferred by me. Either way, I think I filled my brain with a lot of interesting knowledge, but I think my time would have been more enjoyably spent examining the period of my initial interest rather than adding a ton of reading for an inequivalent amount of satisfaction.

[Old-Barbarossa · Rating 4 out of 5]

Chicago appears to have been one large brothel for most of the late 1800s, with the occasional whorehouse and cat house thrown in (you remember the Simpsons episode?), and liberally peppered with bunko men, conmen, and strangely enough loads of Germans (there was a “lager riot” when the town council tried to stop their boozing and sausage eating antics by force of law, seems that it was OK to drink whisky and rum and eat steak though, like a good Amerykan). Anyway, it’s a riveting read by the guy that wrote Gangs Of New York (can you see a theme going through his writing?), full of stabbings, mass murder, larceny…did I mention the brothels?

[amy · Rating 4 out of 5]

I like Chicago history, and I picked up this book because it had a section on HH Holmes (y'know, the creepy serial killer madman from Devil in the White City?) and he fascinates me and gives me creepy chills.

Anyway, the set up of the book is nice, you can flip around to different sections as you like, and thus I mostly read about the murders and prostitutes. Apparently I am not as pure of heart as I like to think.

[Rita · Rating 4 out of 5]

I picked this book up at a used book sale. The original copyright is 1940. It was a wonderful read about the underworld of Chicago starting around 1850 up to the rise of Al Capone. There are some amusing drawings and great old photographs. I find it rather hard to believe the city survived all the murders, corruption, bombings, gunfights, prostitution . . . well, the list is endless. I strongly suggest this book to anybody interested in the history of crime.

[Philip Athans · Rating 5 out of 5]

An outstanding history of Chicago's bloody past. This is a must-read for anyone who's convinced himself that we live in violent, crime-ridden times and if we could only go back to "the good old days" we'd all be better off. Turns out the good old days were overrun with hookers, pimps, "professional rapists", white slavers, serial murderers, drug dealers and addicts, violent muggings, extortion ... The good old days? HA!

[Josh · Rating 2 out of 5]

It was definitely interesting, but the pacing was whacked. It would mention 3 or 4 generations of gangsters in one paragraph, then spend 40 pages on a certain person or group of people. It was hard to remember all of the information when it referenced it later in the book. Read only if you really love Chicago gangsters. Otherwise, save your time.

[Luci · Rating 3 out of 5]

Very dated, but offers a pretty comprehensive look at Chicago gangs during the early days of the city. Some of the terms and words use are from the author's time - 1940's and due to the time of authorship, Asbury gives the reader some pretty salacious details - without being too racy.

[Sjo · Rating 2 out of 5]

Originally written in 1940, this reads a bit antiquated, but provides a good overview of organized crime and political corruption in 1830s to 1930s Chicago. This is a book for Chicago history enthusiasts, and (Sahara alert) reads a bit dry at times. Lots of names, dates, places.

[Kathryn · Rating 5 out of 5]

First published in 1940, this incredibly thorough book covers organized crime in Chicago from 1830 through Capone's reign and reveals that the relationship between politics and crime is nearly as old as the city itself.

[Joe Brunory · Rating 5 out of 5]

A really thorough book covering many of the Chicago legends that I heard about growing up here but didn't know the facts of their evolution. I recommend the book as a must read for anyone interested in early Chicago history.

[Dane Matthew · Rating 2 out of 5]

Informative but pretty dry. Was tough to finish when 70% of the book details top brothels and prostitution (not as exciting as it sounds). I was expecting more detail and coverage of the Mafia , Capone etc..

[Karen · Rating 4 out of 5]

Good if you like more historical books. Chicago was a pretty crazy place!

[harrie kd · Rating 3 out of 5]

my mum picked this up for me in a charity shop. so far it's ok, it's had really mixed reviews but we shall see...

[Sia Marion · Rating 4 out of 5]

This was really interesting. The title was a little on the teasy side compared to the actual content but there truly was a lot of good information inside. Worth the read.

[Jönathan · Rating 5 out of 5]

Extremely interesting.

[Nick · Rating 3 out of 5]

My favorite part was the description of Captain Billy Wells hunting wolves in Bridgeport.

[Bob · Rating 1 out of 5]

This was a stinker.

[Sean Puig · Rating 3 out of 5]

Asbury never disappoints. a good read.