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The Tangled Web: The Life and Death of Richard Cain - Chicago Cop and Mafia Hitman
The Tangled Web tells the dramatic story of detective Richard Cain's criminal career as revealed by his half-brother, Michael. 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 mob families. Eventually executed by shotgun, Dick Cain lived and died in a world of bloodshed and violence, leaving behind a story so outlandish that he has even been suspected of being involved in the assassination of John F. Kennedy.
237 pages, Kindle Edition
First published April 1, 2007
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Displaying 1 - 25 of 25 reviews
November 9, 2017
There is nothing in this book that endears you to Richard Cain. Michael Cain, Richard’s half-brother, actually writes ‘I have found no evidence to suggest Dick Cain had a conscience. His was a life of absolute self-centeredness’. He states that he was a racist, walked out on women he made pregnant and was involved in criminal activities which ranged from possible murder to drug smuggling. I was taken by the title of the book and it being part of an Amazon Kindle daily deal. Some you win, some you lose.
The book has a lot of facts and the author has obviously put in a lot of work which is why I gave it two stars instead of one. When Dick’s closest friends were Chicago mob boss Sam Giancana and FBI Special agent Bill Roemer you expect fireworks but overall I found it an unexciting read on a person I could care less about.
The book has a lot of facts and the author has obviously put in a lot of work which is why I gave it two stars instead of one. When Dick’s closest friends were Chicago mob boss Sam Giancana and FBI Special agent Bill Roemer you expect fireworks but overall I found it an unexciting read on a person I could care less about.
August 18, 2022
The Tangled Web tells the dramatic story of detective Richard Cain's criminal career uncovered by his half-brother, Michael J. Cain. Apparently, the author first went down a conspiracy rabbit hole. According to a biography of Sam Giancana written by his family, Giancana told his younger brother that it was Cain and Charles Nicoletti, not Lee Harvey Oswald, who were in the Texas Book Depository. Michael J. Cain found no evidence to support the rumors that his half-brother was directly involved in the assassination of JFK and indeed found that Richard Cain was at the Criminal Courts Building in Chicago for grand jury testimonial the day of the Kennedy assassination - per a co-worker.
Still what the author did uncover was that Cain was a made cop - a police insider on Giancana's payroll. He parlayed his inside access to protect The Outfit while learning modern techniques, including polygraphing and hypnosis. Perhaps overblowing his credentials, his lie detector work led employment with the Mexican government. Richard also helped train Cuban-Americans for the Bay of Pigs invasion. Later, as A defrocked Chicago cop who spoke Spanish, Cain apparently was in Cuba supporting the failed CIA bid to murder Castro and writing reports in florid prose. (Apparently, he was a wanna-be novelist of some talent.)
This all makes for an engaging life story, somewhat marred by lackluster narration by Clinton Wade.
Still what the author did uncover was that Cain was a made cop - a police insider on Giancana's payroll. He parlayed his inside access to protect The Outfit while learning modern techniques, including polygraphing and hypnosis. Perhaps overblowing his credentials, his lie detector work led employment with the Mexican government. Richard also helped train Cuban-Americans for the Bay of Pigs invasion. Later, as A defrocked Chicago cop who spoke Spanish, Cain apparently was in Cuba supporting the failed CIA bid to murder Castro and writing reports in florid prose. (Apparently, he was a wanna-be novelist of some talent.)
This all makes for an engaging life story, somewhat marred by lackluster narration by Clinton Wade.
August 4, 2020
Interesting mobster
Richard Cain seems less a ruthless killer/robber/all-around bad guy, and more of a man who lived in a fantasy world. Though a world that intersected regularly with the grim reality of the Mafia. He was Irish and Italian, and his life centered on the people and money-making activities of the Mafia.
I'm not sure what made him tick. He needed risk and danger. He lied all the time. He was smart. As his brother points out, he was completely self-centered. Which didn't stop him being charming and oftentimes kind.
The guy was a puzzle, an interesting one. This book is interesting too. If you like Mafia and true crime, this is for you.
Richard Cain seems less a ruthless killer/robber/all-around bad guy, and more of a man who lived in a fantasy world. Though a world that intersected regularly with the grim reality of the Mafia. He was Irish and Italian, and his life centered on the people and money-making activities of the Mafia.
I'm not sure what made him tick. He needed risk and danger. He lied all the time. He was smart. As his brother points out, he was completely self-centered. Which didn't stop him being charming and oftentimes kind.
The guy was a puzzle, an interesting one. This book is interesting too. If you like Mafia and true crime, this is for you.
May 25, 2018
Whenever you read a book about the mob, you never know what you are going to get. Some are really good, and some are really bad. I find few books that are in-between. Having just finished this book, I really do not know how to rate it. The author appears to have done a lot of research into learning about his half-brother; but parts of the story read so incredulously that I question the veracity of the sources.
To begin with, the title is a misnomer. There is no evidence that Cain was a Mafia hitman. This book makes some suggestion that in one clear instance Cain was suspected in a gangland murder. The bulk of the book appears to be more of a rehabilitation of Dick Cain than a biography. The author focuses on specific instances of Cain as a government operative - either with the police, FBI, or CIA. The author appears desperate to show his brother as more of an adventurer than a hoodlum. Again and again, Cain is shown as a patriot trying to do the right thing - kill a predatory pervert (actually his partner killed the pervert), infiltrate Communist organizations, help the former Cuban dictator, supply information on criminals and other unsavory characters. Only after serving a prison term is there clear evidence that Cain worked as a mobster - and that was a brief period of a few years.
Michael Cain also tries to show how different his brother was from other, more authentic hoodlums. Again and again, he tells his readers how educated and smart Cain was. He was fluent in Spanish, and possibly other languages. He was comfortable changing his identity to better fit in with different places, cultures, and peoples. You see reader? he was more James Bond than Don Corleone. Michael Cain does include some disclaimers such as his pathological lying and gaps in the written record. This reviewer objects to a writing style that states action A as factual with evidence; but then adds a disclaimer. So how did Dick Cain get mixed up with the mob? We don't know. He was doing fine as a spy until around 1963 he is a policeman in Chicago and BAM! his old friend Sam Giancana magically appears in the story. Michael Cain explains they were friends from a long time ago.
Documentation and evidence is both everywhere and nowhere in the book. Having read so many books about mobsters by relatives, I expect the author to have some inside knowledge. I am willing to believe that Dick Cain's mother gave him access to hundreds of letters and Cain's passport. I am a little dubious of anyone writing to his mother about his quasi-undercover work in his quasi-government agent job. Some skepticism on Michael Cain's part is warranted. What else is there? Cain interviewed many people who know Dick Cain. Foremost among them is FBI legend Bill Roemer. Roemer wrote several books about his mob-busting days and shows friendliness towards Cain. Michael Cain claims to have gone over FBI informant reports that show Roemer injecting opinion into the reports. In one report, Roemer explained that Cain could become the boss of the Chicago mob. That one brief passage changed my entire outlook on the book and author.
Understand that Roemer is a well-established mob buster. He may have exaggerated his success; but his credentials are solid. Nowhere does he intimate in his books that he thought Cain could become boss. Perhaps Cain thought he could become boss. Roemer could pass that onto his superiors. However, such a plan would involve murdering rivals and implicating the FBI in a scandal much like the one plaguing Boston where they did support one faction against another. Michael Cain even refers to Dick's plan to assassinate rivals on New Years' Day 1973. Where does this information come from? FBI? They are obligated to warn targets of possible murder. Did Roemer accidentally set up his friend to be murdered? Does this sound unbelievable? No seasoned FBI agent would involve the Bureau in a Godfather-style mass murder program. Are these in real FBI reports? Something as big as a plan to assassinate the heads of the Chicago mob is huge and should be at least photographed as evidence because it sounds so far-fetched.
This book might make readers think Dick Cain is the most interesting man in the world. He certainly traveled the world (unless it was all lies). There is not much known about his worldly travels either because he was a secret agent for the CIA or a secret agent for Sam Giancana, the deposed and exiled boss of the Chicago mob. Apparently, Cain and Giancana were ideal potential investors in Middle East casinos and massive oil deals. Even Michael Cain shows some skepticism at these stories asking rhetorically, why would anyone ask a disgraced policeman to become involved in a multinational oil deal between two friendly nations?
Overall, the book was a bit of a disappointment. I was expecting more on a disgraced policeman and Chicago mobster. Instead, more of the book is about Cain's possible government-sponsored / supported / neutral work. Maybe he took it on himself without remuneration. If so, how did he pay his bills? Subterfuge requires money. Even the stories that exposed his corruption appear to be attempting to exonerate him. Once again, Michael Cain interviewed the prosecutor, just before he died, and the prosecutor intimated that they knew they could not convict Dick Cain with just the evidence against him....Only near the end of his life does Dick Cain appear to be a mob guy. I rated the book at three stars because I cannot disprove anything Michael Cain wrote. However, I am very skeptical of his sources or his use of the sources.
To begin with, the title is a misnomer. There is no evidence that Cain was a Mafia hitman. This book makes some suggestion that in one clear instance Cain was suspected in a gangland murder. The bulk of the book appears to be more of a rehabilitation of Dick Cain than a biography. The author focuses on specific instances of Cain as a government operative - either with the police, FBI, or CIA. The author appears desperate to show his brother as more of an adventurer than a hoodlum. Again and again, Cain is shown as a patriot trying to do the right thing - kill a predatory pervert (actually his partner killed the pervert), infiltrate Communist organizations, help the former Cuban dictator, supply information on criminals and other unsavory characters. Only after serving a prison term is there clear evidence that Cain worked as a mobster - and that was a brief period of a few years.
Michael Cain also tries to show how different his brother was from other, more authentic hoodlums. Again and again, he tells his readers how educated and smart Cain was. He was fluent in Spanish, and possibly other languages. He was comfortable changing his identity to better fit in with different places, cultures, and peoples. You see reader? he was more James Bond than Don Corleone. Michael Cain does include some disclaimers such as his pathological lying and gaps in the written record. This reviewer objects to a writing style that states action A as factual with evidence; but then adds a disclaimer. So how did Dick Cain get mixed up with the mob? We don't know. He was doing fine as a spy until around 1963 he is a policeman in Chicago and BAM! his old friend Sam Giancana magically appears in the story. Michael Cain explains they were friends from a long time ago.
Documentation and evidence is both everywhere and nowhere in the book. Having read so many books about mobsters by relatives, I expect the author to have some inside knowledge. I am willing to believe that Dick Cain's mother gave him access to hundreds of letters and Cain's passport. I am a little dubious of anyone writing to his mother about his quasi-undercover work in his quasi-government agent job. Some skepticism on Michael Cain's part is warranted. What else is there? Cain interviewed many people who know Dick Cain. Foremost among them is FBI legend Bill Roemer. Roemer wrote several books about his mob-busting days and shows friendliness towards Cain. Michael Cain claims to have gone over FBI informant reports that show Roemer injecting opinion into the reports. In one report, Roemer explained that Cain could become the boss of the Chicago mob. That one brief passage changed my entire outlook on the book and author.
Understand that Roemer is a well-established mob buster. He may have exaggerated his success; but his credentials are solid. Nowhere does he intimate in his books that he thought Cain could become boss. Perhaps Cain thought he could become boss. Roemer could pass that onto his superiors. However, such a plan would involve murdering rivals and implicating the FBI in a scandal much like the one plaguing Boston where they did support one faction against another. Michael Cain even refers to Dick's plan to assassinate rivals on New Years' Day 1973. Where does this information come from? FBI? They are obligated to warn targets of possible murder. Did Roemer accidentally set up his friend to be murdered? Does this sound unbelievable? No seasoned FBI agent would involve the Bureau in a Godfather-style mass murder program. Are these in real FBI reports? Something as big as a plan to assassinate the heads of the Chicago mob is huge and should be at least photographed as evidence because it sounds so far-fetched.
This book might make readers think Dick Cain is the most interesting man in the world. He certainly traveled the world (unless it was all lies). There is not much known about his worldly travels either because he was a secret agent for the CIA or a secret agent for Sam Giancana, the deposed and exiled boss of the Chicago mob. Apparently, Cain and Giancana were ideal potential investors in Middle East casinos and massive oil deals. Even Michael Cain shows some skepticism at these stories asking rhetorically, why would anyone ask a disgraced policeman to become involved in a multinational oil deal between two friendly nations?
Overall, the book was a bit of a disappointment. I was expecting more on a disgraced policeman and Chicago mobster. Instead, more of the book is about Cain's possible government-sponsored / supported / neutral work. Maybe he took it on himself without remuneration. If so, how did he pay his bills? Subterfuge requires money. Even the stories that exposed his corruption appear to be attempting to exonerate him. Once again, Michael Cain interviewed the prosecutor, just before he died, and the prosecutor intimated that they knew they could not convict Dick Cain with just the evidence against him....Only near the end of his life does Dick Cain appear to be a mob guy. I rated the book at three stars because I cannot disprove anything Michael Cain wrote. However, I am very skeptical of his sources or his use of the sources.
October 21, 2021
This was just okay as far as I'm concerned. It was the story of a guy who played both sides against the middle and eventually lost his life because of it. But the story, was somewhat slow and tedious. It wasn't near as exciting or interesting as I thought it would be.
May 31, 2025
This book got some negative reviews but it is a good one if you're really interested in Chicago history and read every mob book you can find. Its faults are too much detail about certain topics (e.g., Cuba) and not enough specific insights into the outfit itself. Its strengths include the use of primary sources to add perspective to Richard Cain, who was a very mysterious historic figure in Chicago history. But those primary sources (e.g., letters) again, seem to be used as filler - too much detail - in some parts. The book would benefit from a good editor going over it. The author did a great job.
August 30, 2019
Richard (Dick) Cain was a corrupt cop with links to organized crime in Chicago. He also happens to be the half-brother of the author. This is a poorly written, convoluted and disjointed book about a man who may have been a murderer as well as being rotten to the core. He certainly does not deserve to have his name in print, let alone in an entire book dedicated to his corrupt life style. There are absolutely no redeeming features to this book. I'm sorry I wasted my money and time, buying it and then actually reading this drivel!
August 31, 2025
This is a terrific history of Chicago law enforcement and the Outfit in the last century. I knew of many of the names mentioned in this book , who crossed paths with Dick Cain- but I hadn’t heard of him. Fascinating life. As told by his brother, it’s a roller coaster of the powerful and influential in the 1950s through the 1970s. Superbly researched and written, this is a fantastic history of the Chicago Outfit, politics and the pardon the pun, tangled web that surrounds them.
Terrific Book! Congratulations Mr. Michael Cain.
Terrific Book! Congratulations Mr. Michael Cain.
November 19, 2020
The only good thing I can say about this book is that he did have some letters written from Cain to family. The rest of the info was too little for a mob reader that loves details about every crime or event. It’s not that he is a bad writer, but I just don’t feel that Cains life was as eventful as people say and what information was provided just didn’t seem to go very far.
September 12, 2018
Richard Cain was a very unlikable guy. He was narcissistic, self-centered, and a scumbag. I had a hard time reading this book due to the boring writing, but it was informative once you got past the writing.
July 11, 2021
The book was written well but it never got me to where I cared what happened to Dick Cain. Writer is very good though.
August 5, 2021
If you choose the audio version, don’t. The narration was terrible.
July 3, 2023
I honestly couldn't get into this book. It seemed too all over the place, and it dragged my attention away. He played both sides and got killed for it.
November 16, 2024
Richard Cain was a con man posing as an honest cop and used his role to live life dangerously. It's unfortunte that he was not the only one hurt by his actions. The author mentions his twin girls who were on heroin and helped their Dad in some of his schemes.
November 27, 2024
Not that interesting
Never revealed much . He was mob, he got killed. So there was no real narrative or insight into mob or politics or law enforcement.
Never revealed much . He was mob, he got killed. So there was no real narrative or insight into mob or politics or law enforcement.
November 21, 2012
Dick Cain was an interesting character, a cop who was also a "made man" in the mob (he was half Italian and half Irish but I don't believe that Chicago is as strict about that stuff as is New York) who was also informing on the mob to the FBI. William F. Roemer Jr. was Dick's FBI handler and has written about what a great guy and hero Dick was for helping the FBI although some, including the author, believe that Richard was actually planning to use the FBI to take out the bosses in Chicago so that he could take over. Michael Cain was his half-brother but he's significantly younger than Dick and didn't grow up with him (if I recall correctly, Michael mentions that he was 10 years old the last time he saw Dick). This book is really Michael's attempt to learn more about his brother. Unlike some of the other reviewers, I didn't really have a problem with Michael's writing. Michael apparently did a lot of research into his brother and I find it interesting that the most push back he received was not from Richard's underworld associates but from the FBI. There are lots of interesting stories here and I definitely recommend it to anyone with an interest in the Chicago Outfit.
March 9, 2023
A snitch hating snitch
The author claims the subject of this story, Dick Cain, hated snitches and didn't consider himself a snitch, though he was snitching himself. He is portrayed as this wannabe white Knight leading a crusade against organized crime, while snitching on his rivals. Cain was introduced into police work by the Mafia, as an inside man. He was bought into the Chicago Sheriff's Department with funding from Sam Giacano as he didn't meet the requirements to be a cop. There's a lot of jumping around in this story and the dates given seem to overlap in some instances. The way this story jumps all over the calendar, it would take one considerable time to research and verify the accuracy. Several times I've been in one year only to fine contrary information a chapter or two later. Can't tell if its meant as filler or just plain misleading information. Whomever Dick Cain was, he was a SNITCH from day one. He set up his so called friends for personal benefit. I'm pretty sorry I wasted my time on this read. I find it not to be a very good read for myself
It's hhh
The author claims the subject of this story, Dick Cain, hated snitches and didn't consider himself a snitch, though he was snitching himself. He is portrayed as this wannabe white Knight leading a crusade against organized crime, while snitching on his rivals. Cain was introduced into police work by the Mafia, as an inside man. He was bought into the Chicago Sheriff's Department with funding from Sam Giacano as he didn't meet the requirements to be a cop. There's a lot of jumping around in this story and the dates given seem to overlap in some instances. The way this story jumps all over the calendar, it would take one considerable time to research and verify the accuracy. Several times I've been in one year only to fine contrary information a chapter or two later. Can't tell if its meant as filler or just plain misleading information. Whomever Dick Cain was, he was a SNITCH from day one. He set up his so called friends for personal benefit. I'm pretty sorry I wasted my time on this read. I find it not to be a very good read for myself
It's hhh
February 3, 2024
Michael J. Cain's brother, Richard, was a corrupt Chicago cop who was also a "made" member of Chicago's mafia (AKA The Outfit). Richard was murdered by The Outfit in 1973. In The Tangled Web, Richard recounts his brother's bizarre life.
The Tangled Web is a good book, but it's missing so many pieces. Richard was involved with all sorts of big-time Chicago gangsters and politicians. Richard's life took him across the globe. He was involved in anti-Castro activities in Cuba. Also, he was married multiple times and left several children.
The story is good, but the huge holes in this account make it somewhat unsatisfying. I'm glad that I read The Tangled Web, but there are much better mafia books out there.
The Tangled Web is a good book, but it's missing so many pieces. Richard was involved with all sorts of big-time Chicago gangsters and politicians. Richard's life took him across the globe. He was involved in anti-Castro activities in Cuba. Also, he was married multiple times and left several children.
The story is good, but the huge holes in this account make it somewhat unsatisfying. I'm glad that I read The Tangled Web, but there are much better mafia books out there.
May 2, 2008
A decently written book about the life of cop/mobster Dick Cain. Dick Cain was put into the Chicago Police as a mole for the mob. He ended up getting busted in the early 60's and served some time down in Texas. On his release he started to work both sides of the law, as an informant for the FBI and Sam Giancanas personal assistant. He was eventually gunned down on Grand Ave in Chicago in the early 70's. It's still unknown if the mob knew he was an informer.
August 26, 2016
And I thought an Outfit was a set of clothes!
A fascinating book full of detailed facts and evidence about the Chicago mob, actually called The Outfit, this book described an era in Chicago's history that did NOT dwell on Capone. Dick Cain was a complicated man, living a complicated life. A good read if you are interested in the dark, seedy side of life in Chicago during the mid-1900's.
A fascinating book full of detailed facts and evidence about the Chicago mob, actually called The Outfit, this book described an era in Chicago's history that did NOT dwell on Capone. Dick Cain was a complicated man, living a complicated life. A good read if you are interested in the dark, seedy side of life in Chicago during the mid-1900's.
July 11, 2008
Dick Cain was an interesting character but this book suffers from his brother's poor writing and research skills. At one point he describes Bridgeport as being on the westside. To clear up another review for this book, he was killed in Rose's Sandwich Shop on Grand Avenue and according to FBI agent Bill Roemer the Outfit did not know he was an informant.
February 15, 2021
Way toomuch detail
Instead of a recounting if the highlights of Dick Cain's life as a cop and mobster, this was way more than the life and times of George Washington! After waking up about mid-book, I started reading the first page of each chapter and finished the book in record time. I would not recommend it as leisure reading!
Instead of a recounting if the highlights of Dick Cain's life as a cop and mobster, this was way more than the life and times of George Washington! After waking up about mid-book, I started reading the first page of each chapter and finished the book in record time. I would not recommend it as leisure reading!
August 18, 2016
I was so excited about this book and found myself so bored by it. I had to will myself to turn every page. I am finally finished it now and glad i am. This book might be for some but it not for me
August 15, 2020
Very interesting on how corruption, Federal and State governments intwine. This book gives so many in and outs on how it comes about and works.
January 21, 2022
Not very well written. Story seems to ramble all over. Very hard to get get my attention and keep me focused on the path of the story.
Displaying 1 - 25 of 25 reviews