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Non-fiction
The list is neither claimed to be exhaustive nor ranked in any
particular order.
The Chicago Outfit (Images of America) John J.
Binder
A good short history of the Outfit, with lots of interesting photos.
The Outfit: The Role of Chicago's Underworld in the Shaping of
Modern America Gus Russo
Includes a few inaccuracies which any Chicago guy could have set
Russo straight on (like how to spell Spilotro) and some tendentious
moralizing, but a thorough, semi-scholarly history of the Outfit’s
long reign.
When Corruption Was King: How I Helped the Mob Rule Chicago,
Then Brought the Outfit Down
Robert Cooley, Hillel Levin
A first-person tale by an Outfit insider who flipped
and is, consequently, in hiding. Great stuff on the declining Outfit
of recent decades.
The St. Valentine's Day Massacre: The Untold Story of the
Gangland Bloodbath That Brought Down Al Capone William
J. Helmer, Arthur J. Bilek
A new slant on the infamous massacre. Bilek is a respected former Chicago law
enforcement official who fought the Outfit for years.
Accardo: The Genuine Godfather William E. Roemer, Jr.
Roemer was head of the FBI’s organized crime squad in Chicago in the
sixties and seventies. This is the best of his several books. Roemer
was no prose stylist, but he knew all the players, up close and
personal.
Casino: Love and Honor in Las Vegas Nicholas
Pileggi
The movie changed all the names; this is Pileggi’s non-fiction
account of Tony Spilotro’s ill-fated reign in Las Vegas. Excellent
book by a fine writer.
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Fiction
These
books are not necessarily about the Outfit, but they involve
Chicago organized crime in interesting ways.
Eugene Izzi
Izzi was a genuine Chicago tough guy who turned his
experiences into tough-guy novels before dying mysteriously
(probably a suicide) in 1996. The books vary in quality but all show
insider knowledge of Outfit territory. The Take, Bad Guys, The Prime
Roll, King of the Hustlers are recommended.
Steve Monroe, ’57 Chicago and
’46 Chicago
Stylish, hard-boiled tales of gamblers, cops and
other unsavory types in pre-reform Chicago.
Sam Reaves, Dooley’s Back
Cops-and-mobsters morality tale set in contemporary
Chicago. The Outfit ain’t what it used to be, but…

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