Prohibition Chicago

The Northsiders

1925 -- War in Chicago

1926 -- "A Real Goddamn Crazy Place!"

October 11, 1926

October 11, 1926
Part II

St. Valentine's Day

Part I   Introduction
Part II Top Ten Myths
Part III 10 Questions
   (and 10 answers)


Photo Gallery





Selected writings

"...when Prohibition began Hymie Weiss was 22. Despite his youth, veteran detectives considered Weiss the smartest member of the Dion O'Banion gang. In mental agility, they felt, he compared favorably with the wily Torrio. But there was a temperamental difference. Weiss was a hothead who would plunge heedlessly into a situation that would find Torrio holding back pondering calmly."

The Dry and Lawless Years


"Weiss-- the dynamo of hate."

Rattling the Cup On Chicago Crime


"Weiss was a sullen lowering young man with sharp Sinatra-like features and big, dark, ominous eyes."

The Bootleggers and their Era


"In the matter of concentrated hate and unswerving quest for vengeance, [Weiss] stood out, even in the awe-inspiring circles in which he functioned.
He had chased the previously awe-inspiring Torrio out of town. He domineered his own group so that they doubled their influence and income and, after three unprecedented bold efforts to kill Capone, the latter, astounded and alarmed at the vicious determination of this little Pole, was ready to make almost any concession to establish peace. "

Rattling the Cup On Chicago Crime


"Not much room was left in Chicago for rugged individualism. Broadly, any gangster was either a 'Capone guy' or a 'Weiss guy'".

 The Bootleggers and their Era


"Weiss [was] the founder of a new school of lethal technique with his 'taking-him-for-a-ride' formula, which not only motorized murder, but also made the solution of the crime practically impossible."

 Al Capone: The Biography of a Self-Made man


"Weiss presented a daunting mix of intelligence, imagination, guts, pitiless brutality and vicious temper. When photographers tried to snap him, he neither courted them like Capone nor covered up like most others. He'd fix them with a glare and growl, 'You take a picture of me, and I'll kill you.'"

Mr. Capone: The Real-and Complete- Story of Al Capone


"[Weiss was] thin and wiry, with hot black eyes set far apart, tense, tempestuous, vindictive, he was the brainiest member of the gang and the cockiest."

Capone: The Life and World of Al Capone


"Weiss relished the perquisites of the racketeer's life, especially the sumptuous chorus girl with whom he lived, Josephine Libby. 'You'd expect a rich bootlegger to be a man-about-town, always going to nightclubs and having his home full of rowdy friends,' she said of their life together, 'but Earl liked to be with me,... listening to the radio or reading... history and law books. He was crazy about children.'"

Capone: The Man and the Era


"[Weiss] was a combination of brain and brute and said to be the only man Capone ever really feared."

Al Capone: The Biography of a Self-Made man

Fred D. Pasley
Al Capone: The Biography of a Self-Made Man
Garden City, 1930. 355 pp.

The first of four essential Capone biographies, this by Chicago newspaperman Fred Pasley. While it has the advantage of being written during the time these events occurred, it is not the work of a skilled biographer. No details of Capone's life emerge, and the text waddles around with few grounding points. It has been written elsewhere that Capone representatives reviewed and approved its publication, and, conversely, that Capone was infuriated at its publication.
The ending reads like "Alice Through the Looking Glass" on bad bootleg hooch. Excellent accounts of Capone's August 10, 1926, hit attempt against Weiss and Drucci in front of the Standard Oil Building and of the sensational June 9, 1930, murder of fellow newspaperman Jake Lingle. Lively prose with its 1920s crime-reporter lingo, and occasional insights into the tenor of the times.

John Kobler
Capone: The Life and World of Al Capone
G. P. Putnam's Sons, 1971. 409 pp.
A definitive work in the Capone canon. Kobler's exhaustive research is wonderfully supplemented by first person accounts gathered at a time when a number of contemporary newspaper reporters, police, and even criminals, were still alive. Provides clear perspectives of Chicago politics during Prohibition and beyond. This is the first comprehensive work done on Capone's life and it remains a basic reference text for anyone interested in the creation of the greatest criminal empire in American history (Enron aside). Less material on Weiss than in a number of other books. Kobler resists the temptation to speculate on the identities of the St. Valentine's Day massacre gunmen, but presents, of all things, gangster Alvin Karpis' questionable solution: an entire roster of out-of-town hired guns.

Robert J. Schoenberg
Mr. Capone: The Real--and Complete--Story of Al Capone
William Morrow, 1992. 480 pp.
After 41 years between Pasley and Kobler's books, and 21 years since Kobler, two remarkable Capone biographies appear in a two-year period, starting with Schoenberg's excellent 1992 work. Extremely well written and researched, Schoenberg's book provides new information about Capone's early family life and his New York criminal background. In a sense, Schoenberg takes Kobler to the next level, with insight and unique perspectives on many of the characters of the time, forming a coherent sense of people and events. The author's painstakingly documented source materials, extensive use of well-reproduced photos, and ability to provide a sense of immediacy to seventy-year-old history make this book an outstanding read. If you are not a collector, but are interested in Weiss, Capone and Prohibition Chicago, this is is the first of three books I highly recommend to the reader . Note: every book in this bibliography is worth buying and reading, but the majority are of interest to serious readers on the subject, erstwhile researchers, and latent authors.

Laurence Bergreen
Capone: The Man and the Era
Simon & Schuster, 1994. 701 pp.
Laurence Bergreen also broke new ground with further details of Capone's New York upbringing and family history. Specifically, the details of the life of Capone's brother, Vincenzo (aka Richard Hart, a law enforcement officer in Nebraska), provide a fascinating counterpoint to the central story. Bergreen is a skilled writer who brings insight into Capone the man as no other book had previously done. Both Bergreen and Schoenberg expose the myth of Eliot Ness (who, along with his "Untouchables", never fired a single shot in their "war" against Capone). But Bergreen delves deeper into Ness' life, and finds the true story even more compelling than the myth. There are several minor mistakes in the book (as there are in the other bios), but it is two editorial decisions that diminish the book's impact: first, giving short-shrift to the critical role of the Genna brothers in the Torrio/Capone story, and, second, imposing a contrived and clichéd "gang-that-couldn't-shoot-straight" theme on the Northsiders in their war against Capone. It seems that John Torrio, Al Capone, and Jack McGurn took the Northsiders much more seriously than does Bergreen. Extra bonus points for positing the identities of the St. Valentine's Day massacre crew-- and Bergreen's line-up remains much closer to historical reality than do more recently presented speculations of the killers' identities.

Edward D. Sullivan
Rattling the Cup on Chicago Crime
Vanguard, 1929. 214 pp.
Worth the read for the first chapter alone. Otherwise, this is for the advanced student interested in understanding 1920s Chicago via a series of anecdotal chapters written by a newspaperman who was there. Sullivan writes with breezy, stop-the-presses-style prose that lacks scholarly depth but gives one the feel of hearing a series of great stories as told by a slightly windy great uncle. The follow-up text, "Chicago Surrenders"  (1930), features thicker writing and a depressing (but accurate) portrait of a major American city corrupted, amazingly, from top to bottom by a federal law that outlawed the sale of alcoholic beverages. I recommend reading these books by a cozy fire, with a 1992 Domaine de Trevallon.

John Landesco
Organized Crime in Chicago. Part III of The Illinois Crime Survey 1929
University of Chicago Press, 1968 (reprint). 293 pp.
John Landesco's scholarly study of Chicago gangs and organized crime in Chicago spans a period from 1910 through the 1920s. College post-graduate Landesco spent eight years compiling this in-depth sociological survey, published in 1929 as part of the 1,100-page Illinois Crime Survey (soon to be a movie with Paulie Shore). This is a rare, academic approach to understanding the origins of urban crime in early 20th century America. Landesco contrasts the differences and the continuum in gang crime patterns between the period of time when prostitution and gambling were the cornerstones of the rackets, to a time when the addition of Prohibition upped the ante by millions of dollars and hundreds of lives.

John H. Lyle
The Dry and Lawless Years
Prentice-Hall, 1960. 311 pp.
Judge John H. Lyle saw them all-- in person. As a Chicago municipal court judge during the 1920s, Lyle had many of the city's bootleggers brought in front of him in open court. This is a clear and remarkably detailed journey into thirty-year-old history. Lyle's character study of Northsider George Moran, and his detailed dissection of the St. Valentine's Day massacre are particularly outstanding. Again, this is anecdotal history, but at a level far beyond amateur writing (Lyle had the assistance of several former Chicago newspapermen in creating this book). Among the historic writings about that era, Lyle's text is essential material (when you subtract the melodramatic quotes and pontifications). At the end of Lyle's 1960 book, he calls for the eradication of the vestiges of Chicago gangland history as a requirement for Chicago to move beyond its sorted past. Sadly, by the end of that decade, 2122 North Clark Street and the bank of buildings comprising Dion O'Banion's florist shop and Weiss' headquarters were indeed gone-- victims of Mayor Daley's pretension that organized crime never really happened in Chicago.

Kenneth Allsop
The Bootleggers and their Era
Doubleday, 1961. 383 pp.
This is the second of three books I highly recommend to the average reader. Bootleggers is a comprehensive look at the subject matter, wonderfully conceived by a writer of great craft. British author, journalist, and environmentalist Kenneth Allsop gives an expertly written and thorough telling of the remarkable story of Prohibition Chicago, with in-depth profiles of Weiss, O'Banion, Capone, Torrio, and a host of 1920s gangsters. Allsop goes beyond the routine recitation of gangster hits and dates to provide an insightful sociological view of the times, focusing specifically on the pre-Prohibition history of Chicago and on the emergence of jazz music in 1920s Chicago. The author also gives a clear historical picture of city's ever-changing kaleidoscope of political corruption. There are several minor errors in the text, and one glaring omission in the original publication: no index. The 1968 edition corrected this.

Jack McPhaul
Johnny Torrio: First of the Gang Lords
Arlington House, 1970. 489 pp.
Another book by a former Chicago newspaperman, this attempts to stitch together the elusive life story of John Torrio. Torrio was the criminal equivalent of Bill Gates, a visionary who saw what others could not see, and knew exactly how to make it happen. Prohibition was the opportunity, Chicago was the place, and a crime syndicate grossing over $100 million a year was the result. McPhaul's style is typical of the crime-reporter-turned-historian: a lightweight narrative, unending streams of invented conversations, little interest in the sociological aspects of the subject matter. McPhaul does a semi-credible job, given that his subject was extremely reclusive and private, and that Torrio didn't die young (he lived until 1957, leaving a lot of years for an author to research). McPhaul paints a particularly detailed picture of 1910-1924 Chicago, describing Jim Colosimo's turn-of-the-century rackets and how everything changed when alcohol was banned. Loss of downs for the lurid book jacket, suggesting a hulking Torrio hefting a machine gun over the  North Clark Street victims. Why not a skulking Capone lighting a match to the underside of the Hindenberg?

William J. Helmer
The Gun that Made the Twenties Roar
Gun Room Press, 1969. 294, [8] pp.
In the midst of the many biographies and the I-was-there accounts, Bill Helmer's book provides a refreshing sidebar to the proceedings. Academically researched and crisply written, "The Gun that Made the Twenties Roar" tackles the history of the Thompson submachine gun-- a prized utility of Chicago Prohibition gangsters and a world-wide cultural symbol of America thanks to Hollywood movies. Helmer carefully details the original development and manufacture of a weapon that was supposed to be law enforcement's ultimate tool, but instead found its way into the hands of the Chicago gangs of the 1920s and the Midwestern bank robbers of the 1930s. Particularly outstanding are the excellent photo reprints, diagrams, manuals, and advertisements illustrating the times and the weapon.

Curt Johnson with R. Craig Sautter
Wicked City: Chicago from Kenna to Capone
December Press, 1994. 390 pp.
This is a wonderfully conceived and beautifully executed book-- a grand overview of how Chicago's long history of crime and corruption led up to the full-blown excesses of the 1920s. "Wicked City" is a must for anyone interested in this subject, and a wonderfully entertaining read for the everyday Jo (or Joe). Into their delicious base of the city's wild criminal stew, Johnson and Sautter mix a strong portion of tasty political corruption, an excellent spicing of the history of jazz, and sprinkle the entire mix with a cast of real life historical characters whose exploits seem too incredible to be real. There are sections of the book about Jack Dempsey and Red Grange, Louis Armstrong and Theodore Dreiser, the capitalist dynasties that grew as Chicago grew, and, yes, about Capone, Torrio, O'Banion and Weiss. Old data is freshly presented, new twists of fact emerge, and the text is immersed in intelligence and humor. Sit back,
pour a glass of Domaine Tempier rouge and let yourself fall into this amazing history.

To buy any of these books go to: www.amazon.com, www.abebooks.com, www.patterson-smith.com, or www.barnesandnoble.com.