Bugsy Siegel: The Dark Side of the American Dream

by Michael Shnayerson

The story of the notorious Jewish gangster who ascended from impoverished beginnings to the glittering Las Vegas strip

 "[A] brisk-reading chronicle of Siegel’s life and crimes."—Tom Nolan, Wall Street Journal

"Fast-paced and absorbing. . . . With a keen eye for the amusing, and humanizing detail, [Shnayerson] enlivens the traditional rise-and-fall narrative."—Jenna Weissman Joselit, New York Times Book Review

In a brief life that led to a violent end, Benjamin “Bugsy” Siegel (1906–1947) rose from desperate poverty to ill‑gotten riches, from an early‑twentieth‑century family of Ukrainian Jewish immigrants on the Lower East Side to a kingdom of his own making in Las Vegas. In this captivating portrait, author Michael Shnayerson sets out not to absolve Bugsy Siegel but rather to understand him in all his complexity. Through the 1920s, 1930s, and most of the 1940s, Bugsy Siegel and his longtime partner in crime Meyer Lansky engaged in innumerable acts of violence. As World War II came to an end, Siegel saw the potential for a huge, elegant casino resort in the sands of Las Vegas. Jewish gangsters built nearly all of the Vegas casinos that followed. Then, one by one, they disappeared. Siegel’s story laces through a larger, generational story of eastern European Jewish immigrants in the early‑ to mid‑twentieth century.

Genres: Biography, History, Crime, Nonfiction, True Crime, Audiobook, Jewish

248 pages, Hardcover

Published February 9, 2021

Reviews

[Geoff · Rating 4 out of 5]

Brief interesting biography of the Jewish gangster that made Las Vegas what it is today. the most interesting part of the story for me was situating his life in the context of the immigrant experience. Siegel parent's were immigrants who ran up against the realities of the American Dream and had to do low paid labor to survive. Siegel's brother (partially funded by his bother's ill-gotten money) embraced the American Dream and became a doctor, but Siegel himself, viewing how normal society crushed his father, turned his back on the American dream and became a bootlegger and eventually a top West Coast gangster. It was interesting though, to see how Siegel wanted to keep his public record spotless and wanted acceptance in Hollywood and greater Los Angeles. A good introduction to the realities of gang life in the 20th century; makes me want to learn more.

**Thanks to the author, publisher, and NetGalley for a free copy in exchange for an honest review.

[Valerity (Val) · Rating 4 out of 5]

I got this as an audio book to give my eyes a rest, as I’m really having trouble with them. I very much enjoyed listening to this look at the life of Benjamin “Bugsy” Siegel, as I really hadn’t known a lot about him beyond the casino and his gruesome end. It’s a good dive into his life as a Jewish gangster who had to really work his way up from nothing, and became fairly powerful in his own right. He was always just a bit full of himself, and I think it came back to bite him later on. He felt he was invincible and it turned out that he was not. The description of his final evening after he gets home becomes quite graphic and beyond. Overall, it was a good experience, I enjoyed the narrator’s voice and the book was good. Advance electronic review copy was provided by NetGalley, author Michael Shnayerson, and the publisher.

[Federica · Rating 4 out of 5]

Thank you to @goodreads and @tantoraudio for a free copy of this audio book for an honest review.

This is an interesting listen about the gangster Benjamin “Bugsy” Siegel who made Las Vegas as it is now.
It starts from his humble begins up to his death in Los Angeles.
Bugsy was a complicated man; a violent gangster, but also very generous and devoted to his family (even though he left his wife and children for another woman).
Siegel parent's were immigrants who ran up against the realities of the American Dream and had to do low paid labor to survive. Siegel instead turned his back on the American dream and became a gangster.
I love a good autobiography and this is definitely one!

[Deacon Tom (Feeling Better) · Rating 2 out of 5]

Dry and full of narcissistic and immature behavior from people who had stolen power from others.

Pass on this one.

[Susan Paxton · Rating 4 out of 5]

Somewhere there's an alternate Earth where Charlie Luciano was the CEO of General Motors, with Meyer Lansky as his CFO and Ben Seigel his head of marketing, but I digress.

This is an excellent and readable short biography of Benjamin Siegel and the whirlwind life he led, beginning in the mean streets of NYC, followed in short order by his minor-league gang activities with his pal Meyer Lanksy, their mutual introduction to organized crime by Arnold Rothstein, their life-changing meeting with Charlie Luciano and move to the Mob via the Castellammarese War - Seigel being one of the gunmen who shot Joe the Boss Masseria over spaghetti - and his maniac years as a gangster, murderer, lady's man, and lastly the most famous Las Vegas developer of all time, all of it ending on a sofa in LA at the age of 41. It's a bizarre, fast moving tale, and Shnayerson covers it well although the book dots around a bit. Minor gripes: I hate books with faux "torn pages" edges, there could have been more photos, and why Shnayerson keeps insisting that Seigel's right eye was blown across the room when it was the left is just a mystery.

Certainly an unexpected and I think brilliant addition to Yale's "Jewish Lives" series, and a fine intro to one of the most famous gangland figures of the classic Mob era.

[Brittany · Rating 3 out of 5]

Bugsy Siegel's name has been on multiple episodes of true crime and unsolved mysteries podcasts. I saw this book as the opportunity to learn more about his life.

Siegal is an American mobster most famous for creating the Las Vegas Strip. Siegal was always very careful about his outward appearance, which contributed to his success and power. He kept himself clean from the FBI and avoided the law at every turn.

Overall it's an eye opening book about the famous Bugsy. But only really worth reading if you are interested in him.

Narrator notes: painfully slow narrator. I listened at 1.75-2.0

Thank you NetGalley for the free audiobook in exchange for a review.

[Kathy · Rating 4 out of 5]

Well researched story of his life, including the early years. Thanks to Netgalley for the opportunity to listen to this audiobook

[Jesse · Rating 3 out of 5]

Pretty decent biography that moves beyond what I worried at the outset was going to be just a cut-and-paste job, since the references to Albert Fried and Robert Rockaway and Rich Cohen's Jewish-gangster books are thick on the ground in the first few chapters. (Also, surprisingly, a lot from Birmingham's Our Crowd, which I didn't expect.) After that, the historiography ends up being more purposeful (and there's original research in the footnotes), in that Shnayerson attempts to sort through accounts that may or may not correctly credit Siegel for playing supporting and/or planning roles in various hits--though I wanted something a little more final in thinking about what actually IS true here. (To his credit, Shnayerson does come up with a plausible-sounding theory for who killed Siegel and why, at least to my non-expert eyes.)

Big takeaway, though: although he and the other Jewish gangsters retained some vestigial sense of religious/cultural identity and responsibility (there's even an anecdote where Siegel, on vacation in Italy in 1940 with a woman who may have been one of his many lovers or just a rare actual friend, considers shooting one of the Nazis also in town)--some of them paid for siblings and/or children to attend medical school or rabbinical school, in essence Siegel was a classic schnorrer. He persisted in hitting up his Hollywood friends (poor George Raft, who'd sort of escaped the gang milieu in which they'd both come up, in particular) for small, never-to-be-repaid loans; ripped off Billy Wilkerson, who seems to have originated the concept of the Flamingo, the wildly overbudget white whale that led, directly or indirectly, to Siegel's demise, without remorse; sold maybe three times the stock in the hotel that existed in a desperate attempt to keep the lights on. An inspiring sidelight is that apparently Jimmy Stewart, maybe alone among stars, stood up to him.

I suppose where Shnayerson falls a little short in my mind, in that, once we're passed the initial theorizing about what success meant to Siegel and why, we never get back to enough of a final verdict in this case. Considering that I bought this, Ruth Franklin's Anne Frank biography/reputation history, Steve Zipperstein's Philip Roth bio, and Rachel Shteir's Betty Friedan entry, I was hoping for something more. What does putting him in a series with these other figures mean, ultimately? In contrast, this book renewed my appreciation for how powerfully Tod Goldberg captures the whole complex of assimilation/Americanization/exclusion in mid-century, and later, Vegas.

[Martin]

great and breezy. like a newspaper article. the jewish and italian mob. vegas, frank, the movies. mayhem. also, a brother, the doctor

[Erik Hanberg · Rating 5 out of 5]

A really well-done biography. Brief and interesting throughout.

[Valeri Drach · Rating 4 out of 5]

He was a killer but a dashing one. From a poor background, with poor impulse control he cut a swath of blood revenge and isolated acts of kindness. He couldn’t make the Flamingo work but he did have a vision for hat paid off.

[Mardi · Rating 4 out of 5]

I received this audiobook as an advance copy from NetGalley. I never knew much about Ben ‘Bugsy’ Siegel but, true stories about the mafia have always interested me. Steven Jay Cohen is a brilliant narrator and his voice captures the tone of the time. Bugsy lived a tumultuous life. A life that many people were dragged through. He had goodness in his heart for his wife, children and his mistress however, ambition, money and glory brought him to his demise. His greatest glory ... the Flamingo Hotel & Casino (1946) in Las Vegas. This was a great story, a good pace and very busy. There was always something going on. 4/5

[Kerry Pickens · Rating 4 out of 5]

⁶Everyone knows who Bugsy Siegal was, but do they know was a Jewish gangster? The most interesting part of his life to me was about his daughter's burial. Chabad Rabbi Mandy Harlig went to visit a Jewish woman in a Las Vegas hospice, not knowing anything about the woman who had his visit. Millicent Rosen was Siegel's daughter, and the rabbi made the arrangements for her funeral services and to be buried in the Jewish cemetery. As she did not have funds to pay for the burial, I am sure the Chabad picked up the tab. I have a close friend that is a Chabad rabbi, and they routinely visit hospitals and prisons. In fact, a Jewish friend of mine was in a nursing home, and he belonged to a Reform congregation. He told me the only that ever rabbi came to visit him was the Chabad rabbi.

[Ares Crowley · Rating 5 out of 5]

The idea of this incredible charming and suave gangster saving a mama cat and her kittens and detailing a huge regret in his life being not killing Hilter when he had the chance makes him my hero of all time (ignore the murder charges <3)

[Lisa-Michele · Rating 4 out of 5]

Bugsy was a bad dude. This author makes no excuses. I was drawn to the book for the larger history of the thing, especially the Las Vegas hotel history. “Siegel saw the potential for a huge, elegant casino resort in the sands of Las Vegas, a mecca for homecoming GIs and high-rollers alike. Everything was converging - cars making the drive from Los Angeles in shorter time, and with air-conditioning; planes making direct flights…a war-weary generation eager for fun, the naughtier the better.” It was a genius idea. But did it have to be done by the mob? Apparently so. Who else would throw millions at such an audacious spectacle as The Flamingo in 1947?



Siegel was in cahoots with Lucky Luciano, Meyer Lansky, and all the big boys. You might remember them by different names in The Godfather, but you remember them. Shnayerson takes us through Seigel’s tough upbringing, his merciless focus on getting what he wanted, and his incongruent devotion to the Jewish faith. He and Lansky each chose a girl from the Lower East Side to marry in 1927 with a rabbi officiating. Siegel went on to have two daughters whom he adored but also, many, many affairs. The guy seemed a bit unredeemable. “By his own account, Siegel himself killed roughly a dozen men; according to one gangster, he oversaw the contract killings of far more…” I couldn’t help being fascinated by the shocking contradictions of the mobster mentality. What kept me reading was the even larger historical context of first-generation American Jewish men who found the dark, immensely profitable underbelly of the American dream.

[Brooke · Rating 3 out of 5]

After reading the Barbra Streisand Jewish Lives book, I decided I wanted to read more of them. I thought reading this one would be interesting because it's the first book in the Jewish Lives series to not be about an admirable figure. I didn't know much about Bugsy Siegel before this, and I definitely learned a lot.

"Siegel’s story is compelling on its own. But it laces through a larger one, a generational story of eastern European Jewish immigrants in the early to mid-twentieth century who found the doors of their new world closed and so, as gangsters, pursued their own dark version of the American dream."

I found it fascinating to look at Bugsy Siegel's story through a bigger lens. "Barred from most professions by antisemitism, they climbed, instead, the crooked ladder of social mobility." It was interesting to put it into a perspective of a young boy from a Lower East Side Jewish immigrant family who wanted to pursue the American dream. But as the title of the book says, Bugsy Siegel went down the dark side.

"This short biography is meant to keep Bugsy’s memory and importance alive, as a testament without judgment that a century ago, a small band of immigrant Jews did what they had to do to succeed in a harsh new world, assuring that their offspring would get to traverse the bright side of the American dream."

I really found the story so captivating. It read like true crime, which made it more readable than most biographies. If you're into true crime and the history of Vegas/Bugsy Siegel, this would be a great read.

[Tom Schulte · Rating 3 out of 5]

I don't know much about the "Jewish Lives Series". I knew "Bugsy" (who would have that moniker on his biography title) was nominally Jewish, but after reading this, I couldn't tell you what temple he belonged to, who his rabbi was, or who he had seder dinner with. Frequent mention of "Israeli biographers " of Siegel and Meyer Lansky make it apparent this is an industry.

Well, there was a rabbi mentioned as part of his funeral eulogies. Before the funeral there was his murder and a lot of theories are here on who did that or what involved: girlfriend Virginia Hill safely away in Europe as part of deal to keep her profit skimmings? Her brother with his army rifle experience to save her from an abusive relationship? The instantly installed Flamingo operators Gus Greenbaum and/or Moe Sedway? Others? Who knows? All the theories have plausibility to them and maybe some overlap/conspiracy occurred.

Before that this is really a history of Las Vegas made possible by A/C and the vision of people like Siegel. Seigel's inability to delegate and his grandiose plans kept his ventures in the red for a long time, causing grief for his Syndicate backers and may have made his assassination inevitable.

His friendship with Meyer Lansky and actor George Raft are prominent here. Lansky couldn't save him from himself -- his own self-destructive and dangerous impulses -- and sycophants like Raft couldn't give him enough cash and cover to realize his dreams of grandeur.

[Richard · Rating 3 out of 5]

If you're just coming to the history of organized crime this might be a good place to start. All the names fall into place - major and supporting Italian and Jewish gangsters. What was interesting to me were all the shenanigans in putting the Flamingo Hotel together, how Bugsy's ego led him into too many poor decisions. Bugsy is credited with founding modern Las Vegas; what he really did was steal the idea, and much of the money to make it happen, cheating everyone he did business with, including the "syndicate" and the friends who had power over life and death. Also interesting is how his love for Virginia Hill might have tipped the scales that led to his demise. The author covers all the theories of who shot Bugsy, and who set up the hit, and his one big idea is the most interesting of all.

Also interesting were Bugsy's forays into philanthropy - especially funding militant Zionism - and his odd generosity to friends. Here was the guy who robbed Peter, paid Paul, and then robbed Paul to pay Peter back while dropping a few bucks at the track, or into the poor box. It's a good thing Meyer Lansky (the numbers man) was his best friend.

Ben Siegal went to the life of crime in his teens, had his run with big shots, big money, ultra-violence, and high times, and went down a bloody mess at age 41.

[Mike Kennedy · Rating 4 out of 5]

Thank you to @goodreads and @tantoraudio for a free copy of this audio book for an honest review. Very interesting listen about the gangster who is widely credited for making Las Vegas, Benjamin “Bugsy” Siegel. It covers his impoverished humble begins right up to his death in Los Angeles shortly after opening his dream Casino/Resort, The Flamingo, in Las Vegas. Buggy, a name he hated, was a complicated man. He has a violent gangster who was ruthless, but also was very generous and giving to causes. He was deeply devoted to his family, but yet left his wife and children for another women.

I thought Mr.. Shnayerson did an excellent job showing both sides of Bugsy Siegel. He used a variety of sources that lent credence to what he was talking about. He doesn’t shy away from the dark side of Bugsy, but also gives us glimpses of a softer side as referenced in his letter to his estranged wife on how to parent his daughter.

It was an easy listen that told like a story, but still provided a lot of knowledge about the life of Bugsy Siegel. If you are interested in the beginning of “Sin City” or learning more about a famous gangster in his time, this book is well worth you time.

[Marcella Wigg · Rating 3 out of 5]

There's a certain strain in American culture that idealizes the Mob for its machismo, its organization, and its power. Bugsy Siegel shows a decidedly less glamorous reality than some of the more glamorized depictions. Locked out of most paths to career success in a New York awash in anti-semitism and anti-Italian sentiment, ambitious and unscrupulous young men like Meyer Lansky, Lucky Luciano, and Siegel found a path towards some greater success than the sweatshops where their parents worked through violent crime. Siegel and his ilk may have looked dapper, with their tailored suits, but their slick exteriors belied their brutal capacity for violence. As Shnayerson points out, Siegel seemed to enjoy executions, taking on murder assignments even when he had become so influential that there was additional risk attached to him carrying them out himself.

Unlike many biographies, which tend towards the expansive, this was almost too brief and relies on much secondary material (previous, more contemporaneous biographies). It is interesting how familiar Siegel's story is from Moe Greene in The Godfather films, and Virginia Hill and Shnayerson's suggestion that she may have been behind Siegel's ultimate murder were quite intriguing and buck the typical wisdom.

[James Scheid · Rating 3 out of 5]

This is the eighth biography I have read in the JEWISH LIVES series from Yale University Press. Most of the biographies I have read in this series (with the exceptions of Harvey Milk and Disraeli) have been about people involved in the performing arts. This is the only one I read on a Jewish gangster. I knew a little bit about Seigel and his vision that became THE FLAMINGO HOTEL AND CASINO in Las Vegas. Two of the many little tidbits I didn't know was that his career as a bootlegger began at age 14 and he put his younger brother through medical school. Seigel was handsome, glamorous, violent and for a time the toast of Hollywood. His criminality was part of his allure. Movie star, George Raft was one of his friends. Raft himself had a previous career as a criminal before his rise to stardom. Seigel's story is a rags to riches story for he grew up in desperate poverty. He was shot and killed at age 41. There were many who were suspected of being involved, but no one was arrested for his murder. This was the most unusual biography I have read in this series.

[Hannah-rose Russell · Rating 3 out of 5]

As someone who knows very little about American gangsters and the mob, this audiobook was enlightening! I had never heard of Ben (Bugsy) Siegel until last week, so I was fascinated to hear about his life and the infamous reputation he created for himself. From trying his luck in Hollywood, becoming the front runner for casinos in Vegas, to his notorious demise, this book captured Ben Siegel's life perfectly, referring to him as "Gatsby with a pension to kill."

It didn't drag on and allowed readers to get an inside look into the life of this Jewish gangster.

One of my favorite parts has to be when the housewife came to Bugsy's home to see if she could buy his mansion, and he agreed to sell it to her for $1!!

As I set my headphones down for the final time, I feel like I have newfound knowledge of American gangsters' crime life, along with a hunkering to learn more about these people who brought such terror and respect in the USA!

Positive content: 2⭐️
Language: 3⭐️
Sexual content: 2⭐️
Violence: 5⭐️
Age: 16+

*Thank you to NetGalley and the publisher for providing me with a pre-release copy of this book. My thoughts and opinions are entirely my own!*

[Ryan · Rating 3 out of 5]

Here’s a quickie biography of famed gangster Ben Siegel, the man often credited with bringing modern-day Las Vegas to life with The Flamingo hotel-casino in the 1940s. Nattily dressed, ruthless to the core and devilishly handsome, Siegel became obsessed with building the desert resort, running at least $5 million over budget and making a lot of his impatient friends unhappy. His violent murder in June 1947, though, may have been at the hands of Virginia Hill, with whom Siegel shared a stormy romance. Shnayerson depends on previous biographies and crime reports for his book — and still, he’s forced to educated speculation simply because much is unknown. While Siegel’s life has either become legend or clouded by fiction (the 1991 Warren Beatty movie, “Bugsy,” captures an essence more so than what factually happened), only those who know little of Siegel, Meyer Lansky, U.S. organized crime of the era or the history of modern Las Vegas will learn much.

[JCS · Rating 4 out of 5]

What a life! A master of covering his tracks, Benjamin ‘Bugsy’ Siegel had a fascinating life, starting in poverty stricken Brooklyn, finishing in the dazzling excitement of Las Vegas. This is a memorable account of the very colourful life of an ambitious gangster. He was a ruthless and violent, but also charismatic, man who aimed to make money and build a business regardless of the people he had to eliminate to succeed. I found it fascinating that he could be so violent with his business associates and yet so caring about his family. I enjoyed listening to the narrator in this audio book. Thank you to Michael Schnayerson, Stephen Jay Cohen, Net Galley and Tantor Audio for an ARC in exchange for an honest review.

[Jo · Rating 5 out of 5]

Ben “Bugsy” Siegel may have lived fast and died young but he left a lasting imprint on Las Vegas, the town organized crime built.

Michael Shnayerson’s short, gripping biography of the gangster is a page-turning ride through the life and crimes of one of America’s most notorious mobsters. This is a measured, sober look at Siegel. Favoring nuance and complexity, Shnayerson eschews sensationalism and luridness. When a particular story about Siegel’s life is difficult to verify, he cites conflicting versions and he separates myth from what is actually known. He also puts forward his own theory about who murdered Siegel and why.

This fast-paced, crisp and snappy account of Siegel’s life was hard to put down.

[Caleb Lawson · Rating 4 out of 5]

"The plan came off without a hitch. On September 10, 1931, the uniformed faux agents flashed their badges and showed their inspection documents. Once inside the front office, they drew their guns and lined the bodyguards against a wall, warning them to stay silent. Then they burst into Maranzano's private office. The Jewish killer Red Levine, the one who tried not to kill on the Sabbath, stabbed Maranzano six times. (It was a Thursday). Others riddled his bleeding body with bullets. The killers then fled down the back stairs to a waiting car. Some versions put Siegel at the wheel of the getaway car; true or not, he could take gleeful credit, with Lansky and Luciano, for the plan." - Michael Shnayerson

It's a very interesting experience reading a biography of someone you certainly don't want to emulate. I felt like I was watching the Godfather through most of this book. The story of Benjamin "Bugsy" Siegel surely is the dark side of the American dream. Shnayerson's biography condenses Siegel's ruinous, rollercoaster life into an entertaining and accessible read. An illustration of the reality that a life of sin truly ends in tragedy: always in the life to come, and often in this life now.

[Nazary · Rating 4 out of 5]

Pretty solid piece of history that shines a light on early 20th century criminal activity in America. The first two chapters are a little slow (probably because there's so few accounts of Siegel's early childhood) but they take off from there. Having listened to the audiobook I have a new appreciation for Siegel and his role in American history. The author does a good job of presenting the case of Siegel being the central character but also never losing sight of the fact he was a supporting character in so many other stories. It's certainly interesting comparing him to contemporaries like Lansky or Luciano and the chapter on him vacationing in Italy is a hoot.

[David · Rating 4 out of 5]

An entertaining rapid fire look at the life of one of the biggest gangsters of the 20th century. Much is still shrouded in mystery including his death more than 70 years ago. Well written. The writer weighs in at the end with his own opinion of the demise of Bugsy. A name that he hated. Most who knew him didn’t dare use it to his face. He had many friends both in and out of the mob. A seriously flawed man who came up from the slums of New York’s Lower East Side. Always close to Meyer Lansky and Lucky Luciano but in the end they could not save him from himself.

[Mich · Rating 3 out of 5]

This biography of Bugsy Siegel, a mobster of Jewish origin in the 30’s to 50’s traces his rise and fall. He and his gangster associates, often also Jewish, had no qualms about murdering rivals on their way to controlling bootlegging during prohibition and gambling. While the author seems to emphasize his turn to crime due to his impoverished origins, he fails to mention other avenues that Jews in that time turned to, primarily prizefighting. During these times one third of prize fighters were Jewish and 16% were world champs, including names such as Barney Ross and Benny Leonard.

[Marsha · Rating 3 out of 5]

I'm trying to figure out what it was that I really didn't care for about this book. I think my biggest problem was the author's not effectively tying the book and its story together throughout the book.
I really didn't know much about "Bugsy Siegel" (Ben Siegel; he DETESTED the nickname "Bugsy"!)
I truly would be interested in his union connections for personal reasons – My father's brother was very involved in the union seen in New York at that time…). Anyway, it was overall a good look at the past and a review of the Jewish mob and just generally politics and crime at the time.