The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman [Hardcover]

Michael J. Cain (Author)

Book Description

Publication Date: April 1, 2007

“Richard Cain was possibly the most corrupt police official in the history of Chicago.” — Federal Bureau of Investigation

Here is the dramatic story of Detective Richard Cain’s criminal career as revealed by his half-brother. Cain led a double life—one as a well known cop who led raids that landed on the front pages, and the other as a “made man” in one of Chicago’s most notorious mafia crime families. Michael Cain weaves together years of research, interviews, family anecdotes, and rare documents to create a comprehensive biography of this complex, articulate, and self-contradictory criminal genius. In a story that reads like the plot of Martin Scorsese’s The Departed, Cain played both ends against the middle to become a household name in Chicagoland and a notorious figure in both the Mob and the world of Chicago law enforcement. Eventually murdered in a café by two masked men wielding shotguns, he lived and died in a world of bloodshed and violence. Cain left behind a story so outlandish that he has even been accused of being involved in the assassination of President John F. Kennedy.  Filled with fascinating and until-now unknown facts, The Tangled Web tells the full story of this one-man crime wave.

Editorial Reviews

From Publishers Weekly

Richard Cain (1931–1973), shot to death in a Chicago sandwich shop, was most probably murdered by members of the Chicago Mafia. The author, Cain's half-brother, presents in numbing and amateurishly written detail the life of a "made" man who joined the Chicago Police Department to be mobster Sam Giancana's man on the inside. Cain achieved some fame for being an aggressive vice cop, as well as notoriety in the killing of an alleged child molester, although he was cleared of any charges. Through Giancana, Cain became involved in a CIA plot to kill Fidel Castro (though the author found no evidence to support rumors that Cain was connected to the JFK assassination). And thanks to political connections, Cain was eventually appointed chief of the Special Investigations Unit of the Cook County Sheriff's Department. Cain continued to work both sides of the law, was convicted on several charges and spent several years in prison. Despite the author's painstaking research, the descriptions of his subject as an intelligent and handsome man with savoir faire, who dazzled women with his charm and his risk taking, are less convincing than the story of a hardened criminal without a conscience. Photos. (May)
Copyright © Reed Business Information, a division of Reed Elsevier Inc. All rights reserved.

From Booklist

Now a footnote in the history of organized crime, Richard Cain embodied the symbiotic relationship of Chicago's legendary Outfit and the political machine that ran the city. An old friend of perceived Outfit kingpin Sam Giancana, Cain joined the Chicago Police Department in 1956 and quickly rose to vice-squad detective. Simultaneously, he climbed the Outfit's organizational ladder to trusted hit man and errand runner. Cain's half-brother Michael tells his duplicitous story, that of a pragmatic killer whose own demise in a 1973 Mob hit was anything but unexpected, adding valuably to organized-crime annals and Chicago history by matter-of-factly describing the everyday operations of the Outfit's soldiers rather than its capos. Cain remained involved with Giancana right up to the latter's execution-style murder but apparently didn't rank high enough to discern whether Giancana was really in charge or a front for Tony Accardo and Paul Ricca, as recent researchers have posited. Great stuff for a look at the reality of life in the Mob and a window on how the "city that works" really worked. Mike Tribby
Copyright © American Library Association. All rights reserved

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Product Details

• Hardcover: 240 pages
• Publisher: Skyhorse Publishing; First Edition edition (April 1, 2007)
• Language: English
• ISBN-10: 1602390444
• ISBN-13: 978-1602390447
• Product Dimensions: 9 x 5.9 x 1 inches
• Shipping Weight: 14.4 ounces (View shipping rates and policies)
• Average Customer Review: 4.2 out of 5 stars  See all reviews (13 customer reviews)
• Amazon Best Sellers Rank: #1,222,617 in Books (See Top 100 in Books)

Customer Reviews

Most Helpful Customer Reviews

6 of 6 people found the following review helpful:

5.0 out of 5 stars A most fascinating book., May 25, 2007

By 

Robert J. Compau - See all my reviews
(REAL NAME)   

This review is from: The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman (Hardcover)

You have to keep telling yourself that yes, this is a true story. For a leading character that came from such humble, mundane background, Dick Cain let a most extraordinary life. The book does an excellent job of tracking his life, from a pseudo-inside perspective. It adds to the appeal of the book that the author has a vested interest in the subject, but not involved enough to have a stake beyond discovery of the truth. No over the top dramatics but a very straight forward, well told story.

The book leaves you wanting more, which is a good measure of its success. Dick Cain did great things, terrible things, but great. You read his story and he seems to be just a run of the mill tough guy, but by the end of the book you realize just how many adventures he had and just home much of this era's history he saw. It was hard to put down and was told in a very personal, well pace manner.

This is a great view of organized crime from the inside. Not from someone who made it big in a financial sense or a power sense, but from a person who actually survived as long as he did without achieving either of those measures of success. Not a stooge but not a star, which makes it, in my experience, a unique and fascinating book.

3 of 3 people found the following review helpful:

4.0 out of 5 stars DEEP POLITICAL OPERATOR, October 25, 2007

By 

Russ Tarby "Russ Tarby" (Liverpool, N.Y.) - See all my reviews

This review is from: The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman (Hardcover)

One of the most esteemed JFK assassination researchers, Dr. Peter Dale Scott has long been intrigued by the life and times of Richard Cain.
As both a respected cop and a ruthless murderer, Cain personified Scott's assertion that "deep politics," the shady nexus of elected power-brokers and underworld forces, determined the course of history in the 20th century.

As a made member of the Chicago Outfit who also rose to the position of Chief of Special Investigations for the Cook County Sheriff's Police, Cain clearly operated as a deep political player.

This new biography of Cain reveals that he was also an international operator whose travels took him to Mexico, Japan, Colombia and Cuba.
Although he has occasionally been named as a possible shooter and/or conspirator in the JFK hit, Cain is apparently exonerated by this new bio.

The book, with the wordy title "The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman," was written by Cain's half-brother, Michael J. Cain. It includes eight pages of photos.
As a relative of his biographical subject, the author offers many personal observations of Cain as an aspiring Chicago PD cop along with plenty of family history. One amusing anecdote has Cain and his police partner attempting to stab a dead wino's body so they could call in the homicide cops to take the stiff off their hands.

Before Dick Cain rose through the CPD ranks and, in the 1950s, became a bag man for the Outfit delivering payoffs to fellow police officers while guarding the interests of his best friend, Sam Giancana.
As his focus grew national, Cain mastered the operation of the polygraph machine and also became an adept wiretapper, two talents that well-served both his upperworld and his underworld bosses. Cain taught those skills to Mexican authorities and also had considerable contact with CIA operatives whom he hoped to impress with his investigative capabilities.

In a chapter barely more than four pages long, the author deals with the JFK allegations by claiming that on the afternoon of Nov. 22, 1963 Dick Cain was waiting to testify to a grand jury in Chicago. But since he has turned up only one witness to that scenario, Michael Cain's mind remains open. "I welcome any new evidence," he wrote.

Anti-Outfit politicians and Judge Julius Hoffmann (famous for his role in the Chicago Eight trial) sent Dick Cain in prison during the late-1960s, but by 1973 he was back on the street and still scuffling between the Outfit and the Feds. Giancana had been exiled to Mexico, so Cain took up with a burglary crew led by Marshall Caifano, who may have eventually engineered Cain's murder in December '73, at Rose's Sandwich Shop, about a mile from The Loop.

"Corrupt cops lead complicated lives," the author writes, and later, "Dick Cain was a complicated guy, to say the least."
Even though "The Tangled Web" makes few direct contributions to our knowledge of what occurred in Dallas, it paints a vivid portrait of the deep political corruption that was epidemic in major metropolitan centers during the 1950s and '60s.

For that alone, the book sheds important light on a world previously cloaked in darkness, a world in which the killing of a president and the cover-up of his murder was no longer unthinkable but actually inevitable.

3 of 3 people found the following review helpful:

5.0 out of 5 stars Truth is Better Than Fiction, September 19, 2007

By 

John J. Browne "bookaholic" (Brooklyn, New York United States) - See all my reviews
(REAL NAME)   

This review is from: The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman (Hardcover)

Imagine having a half brother who was both a highly decorated police detective and a "made" soldier in Chicago's Giancana crime family. That is the story that unfolds as Michael Cain describes the double life of his half-brother Richard. Richard Cain was rumored to be involved in the CIA plots to assassinate Fidel Castro and he was also named as one of the mob hit men supposedly involved in the assassination of JFK. He was appointed Chief Investigator for the Cook County Sheriff's Department at the same time he was on the payroll of mob boss Sam Giancana. What is amazing is that Richard Cain's corruption was widely suspected yet it did not prevent him from moving up the ranks of law enforcement. Along the way he also found time to bug foreign embassies, pass himself off as a psychologist and become and informant for the FBI. The book is mesmerizing read and covers many aspects of organized crime in Chicago from the 1950's to the early 1970's.