Roaring Twenties Facts That Are Stranger Than Fiction – Guest Post by Renee Rosen, author of Dollface

Two weeks ago I had the pleasure of attending the industry launch party for a really fun new book, Dollface by Renee Rosen. We took a version of the Untouchables Gangster Tour which had been customized a bit to follow some of the characters of the book and then had food and drinks in an authentic 1920s speakeasy.


Our Untouchables tour guide

I had the opportunity to read Dollface before the party and it is a very fun book that provides a great look into 1920s Chicago and in particular the Northside Gang. I was able to chat with Renee Rosen a bit at the party, and she agreed to share a bit more about the Northside Gang with my readers. Check out her post, and then check out Dollface to bring their stories to life.

When it comes to Chicago during the Roaring Twenties, most people think of Al Capone. But when I began doing research for my novel, Dollface, I quickly discovered that the lesser-known gangsters from Chicago’s North Side were a far more colorful and fascinating bunch.

Take for example, Dion O’Banion, the big boss of the North Side Gang. He was a former alter boy and attended Mass every day. He was a florist and such a devoted Catholic that he even opened his flower shop, Schofield’s, directly across the street from Holy Name Cathedral. Now does this sound like a ruthless, murderous gangster to you? Yeah, well, don’t let Dion’s religious practices fool you. He may not have drank a drop of alcohol himself, but he was vicious bootlegger who carried a rosary and three guns and is believed to have whacked more than sixty men before Capone succeeding in gunning him down inside his flower shop.


The door to the speakeasy

With Dion O’Banion out of the way, Hymie Weiss was next in command and took over the North Side Gang. Hymie was another bewildering figured. Widely assumed to be Jewish, Hymie’s real name was Earl J. Wojciechowski. Rumor has it that he borrowed the name from a tailor’s label stitched inside one of his suit coats. Hymie was perhaps the meanest of all gangsters and was the only man Capone admitted being afraid of. Hymie even shot his brother during a family quarrel and was reputed to have shoved a sawed-off shotgun in a U.S. Marshall’s face. He was a somber fellow and like Dion O’Banion, Hymie was a God-fearing, Church-going man. So devout was Hymie Weiss that he supposedly went to church each day and on bended knee prayed to God to help him kill Al Capone. Unfortunately for Hymie, he didn’t pray hard enough because Capone got to him first, gunning him down in front of Holy Name Cathedral. Legend has it that a Bible in Hymie’s breast pocket was the only thing that kept a bullet from entering his heart. Of course it was the other ten slugs that took him out on his way to the hospital. If you go by Holy Name Cathedral today you can still see a bullet hole in the south east cornerstone from that bloody day.

With two North Side members down, it was up to Vincent “the Schemer” Drucci to run the show. Drucci was my favorite gangster and I probably could have written an entire novel just about him. He was an Italian and yet he belonged to the predominantly Irish North Side gang as opposed to the largely Italian South Siders. His nickname “the Schemer” was most befitting, as Drucci was a bit of a whack-a-doo. The best pranks pulled off by the North Side Gang can most likely be traced back to Drucci.

For example, it was Drucci who orchestrated the plot to sneak into one of Capone’s warehouse and replace all their whiskey barrels with barrels of water. One of Drucci’s favorite bits was donning a priest robe for grins and standing across the street from Holy Name, outside of Schofield’s, making lewd comments to women passing by or throwing punches at Dion as passersby looked on in shock at the rowdy priest. Drucci also had a bit of the acting bug in him and starred in a blue film, a.k.a. a porno flick called Bob’s Hot Story.

Drucci was the only gangster of the North Side Gang to die at the hands of the police rather than a rival gang member. And because Drucci had served as a doughboy during WWI and because he had been killed by the police, they felt it was only proper to bury him with full military honors including a 21 gun salute.

You can’t make this stuff up, right? So when people ask me why I chose to write about gangsters during Prohibition and why I chose to focus on the North Side Gang members, all I can say is that these characters were just too good to resist.

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