Second City Sinners: True Crime from Historic Chicago's Deadly Streets

by Jon Seidel

Countless criminals have made their mark on Chicago and the surrounding communities. Chicago Sun-Times journalist Jon Seidel takes readers back in time to the days when H. H. Holmes lurked in his "Murder Castle" and guys named Al Capone and John Dillinger ruled the underworld. Drawing upon years of reporting, and with special access to the Chicago Daily News and Chicago Sun-Times archives, Jon Seidel explains how men like Nathan Leopold, Richard Loeb, and Richard Speck tried to get away with history’s most disturbing crimes.

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Genres: History, True Crime, Nonfiction, Crime

336 pages, Hardcover

First published September 20, 2019

Reviews

[Pam · Rating 4 out of 5]

This is about Second City Sinners by Jon Seidel, not to be confused with Sin in the Second City by Karen Abbott, also a good book, but about sisters who ran an infamous brothel in the early 20th century. Chicago has a colorful crime history worthy of multiple books. Seidel gathers many famous cases so notorious that they are still well known today, and goes back through Chicago newspapers for research. He is a contemporary Chicago journalist who says “you won’t find words like “sexpot” and “mope” anywhere in Chicago newspapers today”. That is why I decided to read his book. I was hopeful that I’d get more of a feel for those well known crimes through his research and that was true to an extent, especially in the early years.

Full page headlines are shown and it is interesting to see how the fonts, spacing and photos have changed. Generally everything looks very crowded and choppy and more difficult to read. The photos are far more sensational with weeping widows, snarling gangsters and noirish angles of dead mobsters on the pavement. It all looks a little messy by today’s standards but gives a feel for the times.

Many famous journalists worked for Chicago papers over the years, including Goldstein and Mulroy, first Chicago newsmen to receive the Pulitzer Prize for their coverage of the infamous Leopold and Loeb thrill kill case. Ben Hecht, Carl Sandburg, Ring Lardner, Mike Royko and Theodore Dreiser are mentioned. Even Ernest Hemingway is found here, not as journalist (which he indeed was for a while). He was buddies with a philanderer nearly murdered by a jilted lover (his gardener wasn’t so lucky, he took the bullet). Many will be familiar with the notorious beautiful jazz age women found in the musical and movie Chicago. Sob sister journalist Maurine Watkins made headlines with their cases, and all that jazz.

Many books cover the individual cases more completely than you see them here. For instance, the H. H. Holmes case in Erik Larson’s Devil in the White City. Many books have done Capone and cronies, but this book has a fresh approach to some of the material. A Daily News source says Capone’s bodyguard during his tax evasion trial (hustled out before the trial began since he was found packing a loaded pistol) was “a guide, philosopher, and friend of Alphonse Capone.” I’m not sure how tongue in cheek that was.

Good list of sources and suggested reading at the end.

[Bimal Patel · Rating 5 out of 5]

Disclaimer: This book was provided to me by the publisher in return of my unbiased opinion/review.

Chicago has always been close to my heart having been lived there for almost 16 years so any chance I get to explore Chicago either through books or taking a stroll through the city is always thrilling. The title of this book intrigued me and hence I decided to read this book. Chicago is known for many things its chilly winters, deep dish pizza but first and foremost its crime. This book focus on the criminal history of Chicago through its criminals. The author has done a wonderful job by piecing together crime stories chronologically using newspaper archives of one of the most prominent newspaper of the time. The stories flow nicely and full of interesting details that is sure to keep the reader glued.
Overall, I really recommend this book to anyone who is interested in history of Chicago.

[Dean Jobb · Rating 5 out of 5]

Few cities can boast as many larger-than-life characters as Chicago. The ruthless Al Capone. Mass murderer Richard Speck, who systematically killed eight student nurses in 1966. H.H. Holmes, the 1890s serial killer immortalized in Erik Larson’s The Devil in the White City. Chicago journalist Jon Seidel retells their stories and introduces more than a dozen lesser-known but prolific killers, terrorists and gangsters in Second City Sinners. He quotes generously from contemporary new reports and witness statements, transporting readers back in time and infusing the narrative with immediacy and color.

[Melissa · Rating 3 out of 5]

If you enjoy Chicago history, have.a listen

[Marsha · Rating 4 out of 5]

I was already familiar with most of these cases. Certainly, having gotten my bachelors degree at U of C, and having lived in Chicago (Hyde Park) until 67, the Leopold and Loeb and the Richard Speck stories had both been important and discussed during my childhood and college. But this book filled in and clarified a fair amount. I remember as a child seeing a movie about the St. Valentine's Day massacre, and being a Chicagoan I have often had that brought up about my town, but this was kind of the first place that I actually got the details about the situation. There was certainly nothing like actually living on the south side of Chicago during the Richard Speck situation! But, having been a small child at the time, I knew only what my parents (who had both become nervous, at best, during the whole circumstance) and unable to totally clarify what had been going on. I have, subsequently, read more about that, but this book was a good consolidation of all of it. And, also of course, having subscribes to The Daily News (well, my parents subscribed) until it went out of business, I love the connection with that newspaper :-)

[Kimberly · Rating 4 out of 5]

Review featured at www.books-n-kisses.com

It might be bad but I have been fascinated by Al Capone for a long time. I really find him an interesting character.

This book emcompasses Capone and so many others. Chicago has been laden with crime that have fascinated the general public over the years and this book adds to the fascination.

I thought this book was really well written and kept my interest. Many I have heard of but some I have not. Being a fan of John Douglas (FBI Profiler) this one fits right in to the same caliber.

Disclaimer:
I received a complimentary copy of the book in exchange for an honest review.

[Ken · Rating 4 out of 5]

Excellent retrospective with the help of news accounts of the worst crimes and criminals in Chicago's history. Al Capone, Leopold & Loeb, and H.H. Holmes ("Devil in the White City") all are part of the Chicago crime scene. Native Chicagoans will recognize street names and intersections where the most infamous crimes occurred. A riveting read.

[Connie · Rating 5 out of 5]

Excellent true crime book that takes you back in time with quotes from Chicago's newspapers and intriguing information about the criminals and crimes! If you enjoy true crime, I highly recommend reading Jon Seidel's book.

[beauty_andbooks · Rating 2 out of 5]

This book is great if you live or know a lot about Chicago. Much of it details particular city streets or corners where crimes took place. It also involves a lot of court room details for each particular crime listed in the book. I for one, do not know anything about Chicago and I’m not that interested in the court room drama of a crime. My interests lay more in knowing nitty gritty details about the crime itself and the person/s committing the crime. There is also a lot of names to keep track of for each crime in the book. All in all, it’s a lot of information to take in for this book. Also, much, if not all of the crimes take part between 1880 to 1940s. So it includes no crimes from present day. There was only one chapter in the book that peaked my interest, and that was the crimes that were inspiration for the broadway play, Chicago. Overall, I don’t think this was a bad book. Just you have to have a particular interest in early 20th century crimes and court room details.

*thank you to netgalley, the author and publisher for the free copy to review

[Tomas · Rating 4 out of 5]

Chicago Crime History Lesson 101.

Jon Seidel did a fantastic job on doing his research upon putting this book together, creating a piece of what was and what is now in the present time.

I learned so much from this book that I didn't know, it's A very informative book, and I highly recommend to any True Crime fanatic.

Rating 4

[Vonda · Rating 5 out of 5]

I thought I knew everything about Capone and the Chicago mobsters. I learned so many things and was completely entralled by the style of writing. Captivating, informative, highly recommended to any true crime junkie.

[Mary Rounds · Rating 4 out of 5]

This was a very interesting collection of stories about past crime in Chicago. I was surprised at the crimes, the persons involved in many of the accounts. And-- how it seems that the present time is really no worse than in the past.

[Samantha (my_read_feed) · Rating 3 out of 5]

Second City Sinners is a compilation of Chicago’s true crime stories with research taken from Chicago’s famous newspapers. The stories are fascinating and are kept relatively short so you won’t get bored.
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I received this book for free from NetGalley in exchange for an honest review. All feelings are my own. I would caution against reading this book if you’re planning on reading any long-form books about the crimes (mostly murders) contained within its pages as the long-form books will have many more details and Second City Sinners might ruin the ending with spoilers.
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Relatedly, though I loved the pictures included in the book—it’s cool to see photographs of the people mentioned—the captions often contained information that spoiled the ending of the story, which I REALLY didn’t like. My e-copy also had a number of formatting problems. I’m sure this was fixed in later e-publications but it was incredibly distracting.
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I enjoyed learning more about my current city but I think I would have liked reading a full true crime book about any/all of the crimes discussed more. The short stories give you all the necessary information, but there really wasn’t much suspense. I like the suspense in my true crime reads.

[Ronnie Cramer · Rating 3 out of 5]

A decent collection of notorious Chicago crimes, as covered by various city newspapers over the years. Includes Leopold & Loeb, Richard Speck, John Dillinger's death outside the Biograph Theatre, the St. Valentine's Day Massacre, H. H. Holmes and others.

[Terry · Rating 4 out of 5]

A wonderful overview of some of the major crimes in Chicago. Some were new to me, but the big ones I had heard of it was nice to know some of the details.
Kept me entertained while stuck in the airport waiting for a flight (that was a total of 9 hours).

[Kat M · Rating 4 out of 5]

I really enjoyed learning about Chicago's crime, it was a interesting read that was well researched and written. I had a good time reading this and learned a little bit too.

[Heather Bennett · Rating 4 out of 5]

Second City Sinners is a interesting and informative book on Chicago's crime. The author has done a lot of research and has written a good book.

[Mary Lou Rounds · Rating 4 out of 5]

Amazing history of Chicago!!

[Robin Brink · Rating 5 out of 5]

Excellent history and details

[William Hubbartt · Rating 5 out of 5]

Fans of Chicago stories and literature will enjoy these true stories from the headlines and news articles describing major crime stories over the years.

[Marybeth Taranow · Rating 3 out of 5]

I really enjoyed this book but I have one caveat, this really should be read I physical form. There are so many pictures and the formatting for ebooks is just not great. I understand that I had an uncorrected copy but it was so hard to follow.

I liked it enough to purchase the physical copy and it really made a difference. I enjoyed all the photos and old clippings from the newspapers. If you like crime and history and Chicago than this is a book for you.

Thank you to the publisher and Netgalley for an advanced copy in exchange for an honest review.
I’m giving this a 3.5

[Phil · Rating 4 out of 5]

Non fiction and historical view of major crimes in Chicago’s past. Each chapter is a new crime and treated as a short story. The author seems to rely upon newspaper accounts (Chicago Daily News) of the crimes which made the stories more interesting. I enjoyed the book and recommend this book to those interested in the true crime genre and like short snippets of major stories.

[Spwalker1962 · Rating 4 out of 5]

This book was written by the husband of one of Judy’s distant cousins. With his knowledge and access to many files working at one of Chicago’s largest newspapers, he tell the stories of some of Chicago’s notorious crimes from Chicago’s early years. Great read for those who love crime dramas and Chicago history.

[Thinking one · Rating 5 out of 5]

Good read about some of Chicago's more infamous crime.

The stories are short but, the articles and pictures take you back to the times that the crimes occurred. I was 10 when the student nurses were killed and even after all this time, I can remember seeing the headlines.

[Eric Porter · Rating 5 out of 5]

Great fast read with some characters from Chicago's past that I didn't know and some that were very familiar. Starts with the first murder in Chicago and goes through the late 60's with everything coming from the old Daily News. Entertaining and informative.

[Justin repking · Rating 3 out of 5]

A great recap of Chicago’s history of criminals.