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Rogues' Gallery: The Birth of Modern Policing and Organized Crime in Gilded Age New York

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From the beginnings of big-city police work to the rise of the Mafia, Rogues' Gallery is a colorful and captivating history of crime and punishment in the bustling streets of Old New York.

Rogues' Gallery
is a sweeping, epic tale of two revolutions, one feeding off the other, that played out on the streets of New York City during an era known as the Gilded Age. For centuries, New York had been a haven of crime. A thief or murderer not caught in the act nearly always got away. But in the early 1870s, an Irish cop by the name of Thomas Byrnes developed new ways to catch criminals. Mug shots and daily line-ups helped witnesses point out culprits; the famed rogues' gallery allowed police to track repeat offenders; and the third-degree interrogation method induced recalcitrant crooks to confess. Byrnes worked cases methodically, interviewing witnesses, analyzing crime scenes, and developing theories that helped close the books on previously unsolvable crimes.

Yet as policing became ever more specialized and efficient, crime itself began to change. Robberies became bolder and more elaborate, murders grew more ruthless and macabre, and the street gangs of old transformed into hierarchal criminal enterprises, giving birth to organized crime, including the Mafia. As the decades unfolded, corrupt cops and clever criminals at times blurred together, giving way to waves of police reform at the hands of men like Theodore Roosevelt.

This is a tale of unforgettable characters: Marm Mandelbaum, a matronly German-immigrant woman who paid off cops and politicians to protect her empire of fencing stolen goods; Clubber Williams, a sadistic policeman who wielded a twenty-six-inch club against suspects, whether they were guilty or not; Danny Driscoll, the murderous leader of the Irish Whyos Gang and perhaps the first crime boss of New York; Big Tim Sullivan, the corrupt Tammany Hall politician who shielded the Whyos from the law; the suave Italian Paul Kelly and the thuggish Jewish gang leader Monk Eastman, whose rival crews engaged in brawls and gunfights all over the Lower East Side; and Joe Petrosino, a Sicilian-born detective who brilliantly pursued early Mafioso and Black Hand extortionists until a fateful trip back to his native Italy.

Set against the backdrop of New York's Gilded Age, with its extremes of plutocratic wealth, tenement poverty, and rising social unrest, Rogues' Gallery is a fascinating story of the origins of modern policing and organized crime in an eventful era with echoes for our own time.

528 pages, Hardcover

Published September 21, 2021

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About the author

John Oller

11 books47 followers

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Displaying 1 - 29 of 29 reviews
Profile Image for Scott.
2,265 reviews269 followers
March 24, 2022
3.5 stars

"[New York City's] 'Gilded Age' ran from the early 1870's until about 1910 . . . The era saw the birth of a new breed of criminal: the organized crime figure . . . The birth of organized crime posed new challenges for the city's police. As the crooks grew in sophistication and professionalism, the police struggled to keep pace. At times [the NYPD] failed, but they were mainly up to the challenge, despite rampant, never-ending corruption both high and low within the force." -- excerpts from pages 8-10

Oller's historical text Rogues' Gallery is an ambitious and well-researched work, and a good chunk of it can be described with three big 'D's - detailed, disheartening, and depressing. (I suppose I can additionally throw in dry for good measure - the first third or so of the book is a steady barrage of criminal names, locales and dates that are sometimes difficult to all keep straight.) However, the involved time period is a very interesting one to focus on - New York City was experiencing major immigrant population growth (Irish, Italian, Chinese, Jews from Eastern Europe), technology was rapidly advancing (such as electric street lights, telephones, the subway system), and the wealthy were living and headquartering their business in the metropolis (Vanderbilt, Rockefeller, etc.). Into this mix were the swiftly organizing ethnic gangs and crews from said immigrant population, often unrepentantly non-stop and violent in their felonious conduct. Meeting them head-on were the sometimes motley officers of the New York City Police, a troubled agency that was only 25 years into its existence at the start of the Gilded Age. The narrative gains traction once the colorful Teddy Roosevelt - soon to be known for his 'Rough Rider' military exploits and two-term U.S. presidency - becomes a police commissioner from 1895 to 1897, and helps reform and repair the agency. The author then profiles some of the honest and hard-working detectives (Thomas Byrnes, Art Carey, and the fascinating Joe Petrosino) whose trailblazing ideas and/or notable investigations pushed the expanding NYPD much more confidently into the 20th century. Rogues' Gallery did not quite meet all of my expectations for some engrossing history, but it was still a relatively good book.
Profile Image for C.S. Poe.
Author 41 books1,314 followers
August 9, 2023
I’ve been so lucky to have gotten my hands on incredible nonfiction as of late, much of it used for research in my own writing, but after reading Rogues’ Gallery by John Oller, I legitimately have book hangover.

Hands down, this is one of the best books I’ve read in years.

Oller is a phenomenal historian, researcher, and skilled storyteller—captivating his audience with the engrossing events and figureheads of Gilded Age New York, all done with a confident author voice, a bit of tongue and cheek humor, and a gifted understanding of how to use end-of-chapter hooks, which isn’t a storytelling tool I’ve seen in nonfiction before and am all about!

Oller walks us through the origins of the NYPD and doesn’t sugarcoat the truth of the department: kickbacks, bribes, assault, political leverage, racism—it’s all there. He digs deep into not only who some of these famous police officers were—Alexander “Clubber” Williams, “Big Tim” Sullivan, Arthur Carey, Joe Petrosino, and of course, the man who arguably changed policing in the United States, Thomas F. Byrnes—but Oller makes these once-living people alive again. He covers Theordore Roosevelt’s time as police commissioner, the Lexow Committee, some of the most famous bank robbers, murderers, confidence men/women, fences, Irish gangsters on the Lower East Side, and the beginnings of the Italian mafia in America as the immigrant population shifted from Irish in the mid-1800s to predominantly Italian near the turn of the century.

Rogues’ Gallery is an accessible, sometimes laugh-out-loud, and fascinating book. Oller’s writing offers ample explanation to those who are new to New York history, while also allowing those of us more versed in the topic to take a real deep dive into some never-before-read facts and nuggets of knowledge. Oller’s notes and selected bibliography are incredibly impressive, and I must say, his tendency to wink, sometimes outright clap back at, Herbert Asbury’s often fantastical Gangs of New York was one of the best inside jokes of the entire book and I’m so glad I slogged through Asbury’s claims before reading this so that those comments could be fully enjoyed! Historian humor at its finest.

I was so excited for the release of this book and enjoyed every single page of it. I’d even argue it should be required reading for anyone researching the history of American policing, crime, or New York City. Because of Oller’s thoroughness, I was able to get a copy of Art Carey’s Memoirs of a Murder Man and I am also planning a trip to Queens to visit the final resting plots for many of these people. I hope Rogues’ Gallery sees more attention and that Oller continues to write us more books in this vein!
Profile Image for Emily.
351 reviews5 followers
Read
October 20, 2024
I’m bailing and donating it to goodwill. Not my fave
Profile Image for Caitlin.
1,084 reviews80 followers
February 14, 2022
Rogues' Gallery is an exploration of policing and crime in Gilded Age New York, following how policework evolved alongside the gangs that dominated the rougher sections of the city and the eventual transition into the mafia families, ending shortly before the rise of Lucky Luciano and the like. Oller doesn't shy away from the corruption and political machinations at work as well as the individuals who did their best to improve a flawed system.

From reading Rogues' Gallery, it's pretty clear that Oller's background is in journalism and law as he makes this comprehensive history of crime in New York City very compelling but is also willing to make some comments on the effectiveness of some of the policies and personalities involved. The amount of research and detail was impressive and I particularly liked Oller's tendency to focus on the people in the time period and provided enough detail to give you a sense of the environment without getting too bogged down in it.

The style of the writing is definitely much more approachable than academic and although I went in knowing basically nothing about the time period, I found it remarkably difficult to put down. Despite some editorializing (and a few moments with somewhat questionable commentary), Oller generally does a good job of remaining fairly unbiased and presenting multiple sides. For some of the more contentious stories, he'll list the possibilities and name the one that he thinks the most likely, which I appreciated. Overall, Oller strikes an excellent balance between an entertaining authorial voice and story and maintaining an accurate historical account.

If you're at all interested in the history of Gilded Age New York City and the evolution of policing and crime in that time period, Rogues' Gallery is a very comprehensive and compelling exploration that I would certainly recommend.
24 reviews
August 26, 2025
I have to be real with you here: I did not finished this book lol! But hey, hear me out, I have attempted to get this right 3 TIMES! But my mind pretty much shut down right around the 30% mark of this book so here’s my review of the first 30% of the book.
1) what is it about? => it’s about the development of the police force as well as the development of organized crime (bank robbery, goods robbery, think ocean 11 vibe$ in the late 19th century in nyc.
2) what’s good abt it?
=> (1) i remember that the opening was very good. The book started with a case where people found 3 pieces of body parts wrapped in fabric being washed ashore by a river. That’s how we are introduced to Detective Burns, who was the one to revolutionize the police force (making them more effective). It was pretty cool how the solve the case: he was tracking down where the fabric be sold at and who they sold the fabric to.
=> (2) overall i find it interesting because most of the crime/mystery-solving nowadays rely a lot in technology like forensic science and DNA detection but before they have that, what do they do? Well this book tells u all abt that 😉
=> (3) 1880s-1890s ocean 11-core!
Profile Image for Amber.
86 reviews1 follower
June 30, 2023
It was fun reading this book right after reading “The Murder of the Century”. This is more the evolution of crime and police work in New York City during the Gilded Age, but started with the very crime “The Murder of the Century” covered.

I was already familiar with main characters and some of the history making this book a more in depth, bigger picture addition.
1,895 reviews55 followers
August 15, 2021
My thanks to NetGalley and the publisher Penguin Group Dutton for an advanced copy of this history book.

John Oller in his book Rogues' Gallery: The Birth of Modern Policing and Organized Crime in Gilded Age New York writes of the origins of the New York Police Department from its earliest days to about the second decade of the twentieth century. The era was one of glitzy murders that made the media go crazy, corruption, racism, brutality, cronyism, nepotism and police reform. The more things change the more things stay the same.

Mr. Oller tells the story by focusing on some of the key players and how they developed the force, or in some cases gave the force a black eye. Some of the key people, Theodore Roosevelt being the most famous, buy also Thomas Byrnes who brought in new techniques such as photograghy and the Bertillon system, and Joseph Petrosino, the first Italian detective who helped to break up early mafia and other criminal gangs. The book is very well written, illustrated and sourced with a readability that never bogs that narrative down. Sort of combination of true crime, history, and sociological study, with a lot of early New York politics. A study of a city finding itself and who different groups fought for both freedom and control.

What I found most interesting was both the influence politicians played on both the police and the criminals they were supposed to be catching. To advance in the department, even to get a good job candidates had to bribe their way in, in hopes of making more money later on bribes that criminals were paying to the police for the politicians who allowed them to do their illegal enterprises.

The story is sometimes not a pretty one. Corruption was everywhere balanced by an equal amount of incompetence and political and personal jealousy. However this is a very interesting and in many ways timely book, as some of the problems of today's police have their origins in their earliest day, unfortunately we keep making the same mistakes. This is a very interesting book and I hope that Mr. Oller continues, as I would like to read about the history of the NYPD. A great book for fans of New York, true crime buffs, criminology fans or people who enjoy well written history books.
Profile Image for Rob McMonigal.
Author 1 book34 followers
January 4, 2023
I'm normally not a huge fan of a book that covers this wide range of a time period, because it's either too little information or too much. But Oller does an amazing job of setting that standard for the reader by providing a solid, lengthy, *engaging* narrative and a ton of reference material and notes for those who want to dig further. It's an approach I wish I saw used more often.

In this case, our time period is roughly post-Civil War New York City up until the Mafia shows up on the scene, roughly covering what's often called the Gilded Age. The marked difference in the way in which criminals operated from the start of the time to the end of it is striking, almost as much as seeing the ways in which the police operated, often in impossible circumstances, either due to corruption (both external and internal), politics, and/or just not having the tools at their disposal.

There's a ton of things done wrong along the way, especially with relation to Tammany Hall, but even the bent cops sometimes/mostly tried to make life safer. The question is for whom, but that's not the point of this look - it's more of a factual statement than an argument for why policing changed and whom it benefitted most (i.e. those with means).

Watching Teddy Roosevelt blast his way into the narrative and blast his way out is a lot of fun, as is learning some really "cool" details about crime innovations and the ways in which scams changed over time. It's also always interesting to see who starts on the outside of the power circle and how they move inward over time, with the corrupt and the criminals adjusting on the fly.

What I liked best was the engaging text by Oller, who keeps the extensive prose fresh and light, with a great, storytelling style that brings these larger and life characters to the fore, with pictures to help us visualize them.

All in all, a great work from a time period I don't know nearly enough about and now have some ideas to springboard from...
Profile Image for Jake.
2,053 reviews70 followers
March 27, 2023
I was jonesing for a New York City gangster tale last week. I finally started Herbert Asbury’s Gangs of New York but quit when I realize that the book is less glorious embellishment and more fan fiction. Frustrated, I looked for a substitute and then remembered I purchased John Oller’s Rogues’ Gallery on a lark.

It aspires to be a corrective to Asbury’s highly fictionalized accounting which was held as a historical standard for years. Oller is more scholarly than smooth but this might scratch the itch if you’re looking for it. It talks about how large scale crime evolved in New York City from the end of the Civil War to the beginning of Prohibition, along with the methods and persons responsible for policing (or not) the city.

One of the big myths it dispelled, among others, is how the Five Points was a crime ridden slum. There were slummy parts and, of course, there was crime. But by and large most of the folks who lived in the Five Points were working class immigrants just trying to get by. It humanizes the city, as opposed to its cartoonish portrayals.

It’s not a comprehensive take by any means but its readable efficiency is owed to the fact that Oller picks one crime at a time, looks at it from both sides over several chapters and then writes out the historically accepted climax. I read some reviews saying that such a style frustrated folks. And I get it; this is very much a Your Mileage May Vary kinda read.

But it worked for me. It gave me a decent outlook into the growth of New York City (though I do need to finish Lucy Sante’s Low Life) and how criminality functioned, especially within the NYPD. I’ve always preferred facts with my non-fiction so I appreciated what it was trying to do.
Profile Image for Mme Forte.
1,110 reviews7 followers
January 6, 2024
I (possibly inappropriately) enjoyed this book quite a lot.

"Rogues' Gallery" is an interesting combination of history and true crime. In it, the reader gets a history of criminal activity in New York, with its many bad guys (and at least one really bad gal), gans of bad guys, and the toll their activities took on themselves, each other, and the populace of the city. It's also a history -- in pieces -- of the NYPD. The time before its creation, its early days, and the developments in management and forensics that took place then are all covered in at least some detail. But don't be fooled: Even the good guys are bad guys sometimes. Corruption and graft were rampant in those days, and the police struggled with policing themselves almost as much as they worked to control crime on the streets.

There are also a couple of accounts of cases worked by some prominent detectives and officials, like Thomas Byrnes, Art Carey, and Joseph Petrosino. This gives the book its true-crime finish, where you see the crimes occur, watch the police gather evidence and follow leads, and eventually get the disposition of the cases in court. And more often than not...the expected and hoped-for outcome is not what you get. I wondered how much better the results would have been for the dogged and methodical cops if they had the benefit of the science that today's law enforcement entities enjoy.

All in all, an informative and interesting read. One caveat: I wish the author hadn't expended quite so much effort telling the reader how repulsive the hand of a certain Italian villain was. That went way over the top. A little more sensitivity and compassion would have been appreciated.
Profile Image for patrick Lorelli.
3,768 reviews37 followers
March 7, 2024
This was really about how a cop by the name of Thomas Byrne in the 1870s began keeping track and recording the different criminals in New York City. He would notice or begin noticing that many would be the same over time but no one had any record of them. He began keeping descriptions, later photos, and fingerprints. Later in the book you are introduced to a woman Marm Mandelbaum was one of the first who had an organization of criminals that she financed to do different jobs, robbery, also a bank, forgery, and others. He needed help and not having anything he came up with his plan to begin taking down the criminal organizations. A very good book and I found it to be very fascinating as well. I received this book from Netgalley.com
434 reviews3 followers
June 10, 2022
I find myself enjoying historical crime fiction. In this well executed and researched book the author tells the story of crime and policing in guilded age New York. He covers the rise of gangsters and the modern police system, police reform and some famous crimes. I got the feeling of what it must have been like in some of these dirty streets so the writing was compelling, and I breezed through this book. I want to check out more by this author- some of the characters he unearthed feel fictional yet all are real.
Profile Image for Sophie L.
83 reviews
January 6, 2025
Long on examples and short on demonstrating any actual structural change. Felt more like a gloss of cops and crooks than a book examining structural change in NYPD. Missing a lot of meat in comparison and instead is mostly narrative based about how the force changed under specific leaders (but even then, it's really more about the lives of those leaders). Would have liked to see more synthesis of research. But, you'll certainly know a lot about crime in New York!
795 reviews12 followers
May 21, 2021
An extremely interesting novel regarding the early days of the New York City police. I found the stories and political intrigue that occurred to be especially riveting. It was truly an eye-opening experience. I fully recommend this book to all true crime and historical fans!

Thank you to #NetGalley and the Penguin Group for the ARC in exchange for my honest review.
Profile Image for Ernest Spoon.
677 reviews19 followers
March 6, 2022
From The Few Bad Apples File...

Enjoyable history of the New York police department from its early days as little more than an Irish-American extortion gang to the model of the modern, metropolitan police force. This book is full of colorful characters and anecdotes, with author John Oller correcting the record, in many cases.
Profile Image for Brett Van Gaasbeek.
466 reviews3 followers
January 6, 2025
Interesting topic, but Oller gets bogged down in the details of the investigation into the NYPD under Byrnes so much that it drags along slowly. You would need to be very interested in the topic to weather the pages of the investigation and the day-to-day minutia of the aftermath. It picked up with the advent of Teddy Roosevelt becoming involved, but it was still slow.
Profile Image for Windy.
658 reviews1 follower
January 10, 2025
I would really call this about 3.5 stars, so i rounded up. I found parts of this history to be intriguing, but a lot was dry and difficult to slog through and keep straight. I particularly enjoyed the details regarding Theodore Roosevelt, as well as various connections made (not just with TR, but throughout the book).
Profile Image for Tyler.
751 reviews26 followers
October 17, 2021
Solid overview of turn of the century NYC crime. There's a big section of Parkhurst trials which I had read before but there's was a lot I hadn't heard of. If you're new to this time in NYC, it's as good place to start.
Profile Image for Ietrio.
6,949 reviews24 followers
June 27, 2022
Sounds like another White man trying to explain why people need to be disarmed, and the armed thugs need to rule their lives, about how Brown young men have to die, so he could feel safe among his hoarding. Maybe I'm wrong. I'll be back when I have read the book.
Profile Image for Sonic.
2,379 reviews66 followers
December 29, 2022
I just did not get into the narrator of the audiobook,... it sounded like he was reading Headlines the whole time in a bland voice that tried to imitate excitement yet somehow sounded flat. The book itself was interesting and parts of it came alive for me, but overall, it did not thrill me.
82 reviews8 followers
June 20, 2024
A window into the development of modern policing through following the lives and careers of Thomas Byrnes, Arthur Carey, and Joseph Petrosino. Well paced, informative; it will leave you looking for more on the period.
515 reviews8 followers
January 8, 2022
This is an entertaining and informative book about policing and crime during the gilded age in New York.
Profile Image for Timothy.
Author 11 books29 followers
January 20, 2022
Well written and interesting study of the NYPD at the turn of the 30th century. Sources are diverse, stories are clever, and the characters stand out. Although history, it reads like fiction.
Profile Image for book worm.
42 reviews
Read
January 31, 2022
Fun-to-read history of things like early surveillance systems and role of Wall Street in developing policing but way too pro-cop for me 🤷🏻‍♀️
Profile Image for Tyler Talley.
277 reviews1 follower
February 13, 2022
Love learning more about this era in American history, endlessly fascinating.
8 reviews
July 18, 2025
A fun read, liked the pictures a lot and it covers a ton of individuals throughout the 1800s and early 1900s
Profile Image for Paul Daly.
354 reviews5 followers
October 30, 2021
Well-researched, meticulously footnoted, carefully indexed history of Gilded Age New York crime and crime fighters, with the towering figure of Thomas Byrnes of the NYPD at its center. Docked a star for describing Wicklow-born New York-raised Byrnes as having a "cockney" accent. Twice.
Profile Image for Rob Atkinson.
261 reviews19 followers
May 5, 2025
A top notch, engagingly written account of New York City’s early policing and organized crime outfits, spanning the era from just after the Civil War through World War I.

On the police side, we encounter a bevy of colorful characters: corrupt and sometimes brutal figures like “Clubber” Williams, “Big Bill” Devery, the influential but flawed Police Commissioner Thomas Byrnes, and reformers like future President Theodore Roosevelt and Detective Giuseppe (Joseph) Petrosino, who fought to expunge the force of its culture of graft and Tammany nepotism, while improving its effectiveness and integrity. Important innovations like the mug shot (represented in Byrnes’s eponymous “Rogue’s Gallery”) occurred in this period, some of which are still standard practice; others, like Byrne’s “third degree” manner of interrogation, are largely behind us, thankfully, though one can see why they were embraced in the period. Reformers fought not just a culture of corruption, but also resistance from the swelling immigrant population in their attempts to enforce the law; their views reflected an elitist and nativist approach to those same communities, who naturally didn’t trust them and the largely Irish police force to look out for their best interests. The aforementioned Petrosino was a major catalyst in addressing this problem with the Italian community, and his tangle with both the police brass and the early Mafia in doing so is a fascinating story in itself.

The criminal element documented here includes the waning days of Irish gangs like the notorious Whyos, as they were supplanted by even more vicious Italian and Jewish outfits which would coalesce into the modern Mafia by the narrative’s end. In the early 20th c., rogue extortionists known as “The Black Hand” would pose yet another challenge to an evolving police force struggling to maintain a semblance of order, while still occasionally having to police itself.

Highly recommended for New York history buffs and/or fans of true crime.
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