42 | DECEMBER 23 • 2021 

ARTS&LIFE
BOOK REVIEW

B

enjamin “Bugsy” Seigel was not a 
good Jewish boy. Siegel led the life 
of a “bootlegger, racketeer, gambler 
and murderer.
” To paraphrase journalist 
James Traub, he “does not deserve our admi-
ration; but like some other 
figures who have yoked their 
lives to deplorable causes, 
he nevertheless deserves our 
attention.
” 
In his new book, Bugsy 
Siegel: The Dark Side of the 
American Dream, author 
Michael Beahan Shnayerson 
presents a splendid his-
tory about, arguably, the most famous 
Jewish gangster in history, who is indeed 
worth “our attention.
” It is a story of early 
20th-century Jewish immi-
grant life in America; of 
bootlegging and the “Roaring 
Twenties;” and of dreams in 
Hollywood and Las Vegas. 
Siegel is a fascinating product 
of all the above. 
Shnayerson is an American 
journalist and contributing 
editor for Vanity Fair mag-
azine. The author of eight 
books and more than 75 
Vanity Fair stories, his book 
about Siegel is published 
under Yale University Press’ 
prestigious Jewish Lives series. 
As Shnayerson notes, those biographies “are 
all of admirable figures … Until now.
”
Siegel was the son of Jewish immigrants 
from Galicia. Max and Jennie arrived in 
America in 1900 amidst a wave of 1 million 
Jewish immigrants. Like thousands of their 
compatriots, they settled in New York City’s 
impoverished lower east side. Benjamin was 
born there in 1906.
Shnayerson relates Siegel’s life in three 
overarching eras. During the first phase, 

Siegel became a petty crook by age 14. 
Hot-tempered and fearless, he was the 
“toughest kid on the street;” hence, the 
nickname “Bugsy.
” As a teenager, Siegel 
also became a lifelong friend and accom-
plice of another highly successful Jewish 
gangster, Meyer Lansky.
Siegel hated the nickname “Bugsy.
” 
Only the most foolish or incredibly brave 
called him “Bugsy” to his face. Siegel pre-
ferred “Ben.
”
A “gangster capitalist,
” Siegel chose an 
alternative career path to rise above poverty. 
He made a fortune as a young bootlegger 
during Prohibition, quickly achieving a 
dream that he shared with other Jewish 
immigrants — prosperity and materi-
al well-being. Siegel’s ultimate goal was 
the attainment of “class.
” He 
declared: “That’s the only thing 
that counts in life … without 
class and style, a man’s a bum.
” 
The end of Prohibition sig-
naled the next phase of Siegel’s 
career. Lansky and Siegel 
became partners with Jewish, 
Italian, Irish and other gang-
sters to form a national crime 
organization: the Syndicate. 
To expand the Syndicate’s 
operations, Siegel was sent to 
California, where he became 
enamored of Hollywood. 
Calling himself a “sportsman,
” 
Siegel spent much of his time at local racing 
tracks and entertaining Hollywood’s leading 
actors and actresses at his mansion. For a 
brief time, he even fancied a career as an 
actor — all while doing his best to control 
as many illegal enterprises in California as 
possible. 
Although married for many years with 
two children — his wife and family were 
always well-provided for — Siegel was a 
womanizer. He eventually developed a long 

and 
tumultuous relationship 
with Virginia Hill. For a few years, Siegel 
was a celebrity … until he was prosecuted 
in a well-publicized murder trial. Eventually 
cleared of the crime (in which he likely 
participated), his glory days among the 
Hollywood set were over.
Siegel’s final phase was an obsession. 
He envisioned building a new, Monte 
Carlo-style luxury casino among the small 
“sawdust-on-the-floor” gambling houses 
of sleepy 1940s Las Vegas. His Flamingo 
Casino eventually became the first such 
casino in modern Las Vegas. The 1981 
movie, Bugsy, visually captures this era, as 
well as Siegel’s California days.
Siegel did not live to see its final success. 
Cost overruns, chaotic project management 
and, worst of all, rumors that he was skim-
ming money — a sin of high magnitude 
among his gangster financial supporters — 
led to his demise. Siegel was assassinated on 
June 20, 1947. The case remains unsolved, 
but Shnayerson provides his best guess as to 
the culprit.
Shnayerson has written an excellent 
biography, the best on Siegel to date. His 
research includes the extensive literature 
about Seigel, as well as new sources such as 
FBI files and his personal interviews with 
Siegel’s living family and acquaintances. 
Most important, Shnayerson thoughtfully 
explores the historical, cultural and Jewish 
context of the era that produced Benjamin 
Siegel. The result is a well-written, insightful 
narrative. It is a bona fide page-turner. 

“Bugsy Siegel: 
The Dark Side of the 
American Dream”

Michael Beahan 
Shnayerson 

Mike Smith
Alene and 
Graham Landau 
Archivist Chair

