The Tangled Web: The Life and Death of Richard Cain-Chicago Cop and Hitman

The Tangled Web: The Life and Death of Richard Cain-Chicago Cop and Hitman

by Michael J. Cain, Jack Clarke

NOOK BookProprietary (eBook - Proprietary)

View All Available Formats & Editions

Available on Compatible NOOK Devices and the free NOOK Apps.
WANT A NOOK?  Explore Now


The Tangled Web tells the dramatic story of Detective Richard Cain, the man the FBI described as “possibly the most corrupt police official in the history of Chicago.” Cain led double life—at once a chief investigator and a “made” man, both a detective who led raids on gambling rings and a soldier carrying out hits for Mafia bosses. Using years of research, interviews, family anecdotes, and rare documents, Michael Cain creates a comprehensive and compelling biography of his half-brother. This edition features an all-new introduction by the author. 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 Chicago and a notorious figure in both the Mob and the world of Chicago law enforcement. Before his execution by shotgun in Rose’s Sandwich Shop, Cain’s legend would grow to the point of rumored involvement in the assassination of John F. Kennedy and the FBI’s plot to assassinate Fidel Castro. Filled with fascinating and until-now unknown facts, The Tangled Web tells the full story of this one-man crime wave.

Product Details

ISBN-13: 9781510722842
Publisher: Skyhorse
Publication date: 02/20/2018
Format: NOOK Book
Pages: 256
Sales rank: 38,436
File size: 3 MB

About the Author

Michael J. Cain researched the story of his half-brother Richard with the help of federal agencies, local police departments, and sources on the street from Chicago to Washington, DC. A native of Michigan, now living in Georgia, Michael is currently working on his fifth book, a novel which explores the world of Army Special Operations in wartime.
Jack Clarke was a legendary Chicago private investigator who worked for Mayor Richard J. Daley and several former Illinois governors.

Read an Excerpt


It was Christmastime, 1973. I had recently been transferred to Memphis to work as the controller of Eller Outdoor Advertising. My wife and I were flying from our new home there to spend the holidays with my family in Bay City, Michigan. We made an intermediate stop at O'Hare with a two-hour layover, so I decided to call some relatives in the area to wish them a Merry Christmas. First on the list was my Aunt Virginia.

"Isn't it awful what happened to Dick?" she said.

"What are you talking about?" I asked.

"Oh my God, you haven't heard. Just go buy a Chicago newspaper and you can call me back if you like."

I hurried down the concourse until I found a Chicago Tribune vending machine. The headline read: EX-COP CAIN SHOT TO DEATH. My hands were trembling as I dropped a dime in the slot and pulled a copy of the paper. Then I bought the Sun-Times and walked back to the waiting area to sit there and read the news about my brother.

I wasn't so much surprised that he'd been killed — I knew he'd been living life on the edge — but the public nature of his death stunned me. I recall wondering if he was killed as a lesson for someone else, or whether he was really involved in something big enough to have caused his murder in broad daylight in a West Side Chicago diner.

By the time we arrived in Bay City, I was pretty much up to speed on what the public knew and was anxious for more details. My father picked us up at the airport and, as we drove away, I waited for him to say something about the death of his first-born son, and perhaps an explanation for why no one had told me. How could that be? How could they not tell me? But he simply drove on, silent, impassive. Finally I asked, afraid that maybe he didn't even know.

That wasn't the case at all. It was just something he'd filed away already. This was how John (J. B., as we called him) dealt with difficult issues. When we had a discussion about almost any sensitive topic, he shut down, clammed up. His lips got thin, his jaw set; that was the signal. In other words, you deal with it by not dealing with it at all.

I was furious; how could he not have told me? But fury wasn't an emotion the children of John Cain were allowed. He'd only really seen me angry with him once, and that was the day I moved out of his house. Anger, rage, and fury; that was his turf, not ours. He refused to discuss Dick's death with me. Worse yet, my siblings seemed reluctant to talk as well, though their silence was born more of a lack of information, since my father wouldn't talk with them about it, either. So we went on with Christmas pretending that nothing had happened.

J. B. had called my sister, Mary Ellyn, who was living in Ann Arbor at the time. Maybe because Dick had been closer to her than to the rest of us, or perhaps she was just the first one on his list. She asked where Dick had been killed, and when J. B. told her in Chicago, she asked, "What was he doing in Chicago?"

"Where else would he be?" was his reply. She realized then that J. B. hadn't any idea what Dick had been up to lately. Mary Ellyn had recently gotten a postcard from Brazil, so she knew he'd been out of the country and thought it was permanent. She was surprised he would have gone back to Chicago, since she assumed he'd left because he sensed some danger there.

The next day she drove to Bay City, anxious to talk about it, and was frustrated by J. B.'s reticence. It was as if he believed if he didn't talk about it, didn't address the death of his son in any way, he wouldn't hurt. He knew at the time that Dick had chosen the road less traveled, but he couldn't have known with any certainty that his son was a bad guy. Even if he did, Dick was still his son.

In an effort to talk about it with someone, Mary Ellyn went to the home of a close friend in town whose husband was a reporter for the Bay City Times. The wife offered an empathetic shoulder while her husband took notes. And as reporters are wont to do, he called in a story about the son of a local resident who was a mobster in Chicago and had been murdered there. J. B. was angry beyond words when he read the story a few days later, and Mary Ellyn was furious with herself. She hadn't gone to her friend to become part of a story; she'd gone to share her grief. She felt betrayed, and still does.

The following week, the Chicago Tribune declared that thieves had killed Dick. Their story was that he had been involved with a burglary ring and that something had gone terribly wrong amongst the burglars, resulting in Dick's murder.

I was determined to understand who killed him and why, but then and there was neither the time nor the place for me to press it. As it turned out, the time and place wouldn't present themselves for several more years, after I'd moved to the Bay Area of Northern California.

My father's relationship with Dick had always been a mystery to me. Dick was seventeen years older than I, and he joined the Army before I was born. When I was a kid we'd see him frequently, or so it seemed to me. He lived near us for a time, and when he was a Chicago cop he'd drive to Michigan on occasion. He'd have one wife or another in tow and a couple or three kids, depending on which wife. Everyone was happy to see him, especially me. He'd tell stories about chasing the bad guys and we'd all listen with rapt attention. Dick was not only a great storyteller; he had great stories to tell. He'd lived in Bay City for a brief period with his first wife. Ultimately, he began to face the reality that he would never be very close to his father. They would disagree on almost every topic, and underlying it all was John Cain's deep-seated hatred for Dick's mother, Lydia, who had been his first wife. I've never known anyone who carried that level of contempt for so many years. She apparently deserved it, if one is to believe the stories my father told about her.

John and Lydia had been married in 1930, just as the depression was kicking off, but John Cain had the good fortune of having a steady, secure job. He was a bricklayer at Republic Steel, keeping the furnaces working. It was hard work and sometimes dangerous, but it was good work at a time when a lot of people were selling apples on street corners. So he had money when others were struggling, and that was likely part of what drew Lydia to him. That, and his devil-may-care attitude about life in general. But she had a mean streak that dug into him like a hot poker.

One story he told me was about a radio he'd saved for and bought. He'd paid a hundred dollars for it, no small purchase in those days. He loved listening to the radio, and in the days before television it was great entertainment. One day, Lydia decided he was listening to the radio when he should have been listening to her and she threw it out the window of their second-story apartment. He told me that it took all the power of his will not to kill her that day. He left for three days to calm down.

So I went home to Memphis after that Christmas of 1973 with a million questions. I hadn't seen Dick for more than ten years, but he was still family. I bought all the Chicago papers, I even found an article about his death in the New York Times. I didn't talk about him much at work. I figured that if he was actually in the Mafia, spreading that news would only complicate my own life.

I'd done some volunteer work for St. Jude's Hospital during my Memphis days, and received an invitation to a fund-raising dinner in Chicago. The featured speaker at the event was Jack Mabley, famed Chicago columnist and a man I knew from his writing to have been a friend to Dick. I couldn't make the event, but a friend who was going agreed to pass a note to Mabley on my behalf. The note, written on the back of my business card, read, "I'm Dick Cain's brother and I'd like to talk with you."

Jack called me the next week and said that he was surprised to hear from me. He'd been told about our side of the family, but assumed we were well out of Dick's life. He had some information to share with me, but he was uncomfortable telling me about it on the phone. When could I come to Chicago?

It took a couple of weeks to work it out, but I flew to Chicago. My brother Bill and I met with Jack at the Chicago Tribune. He told me that on the day after Dick died, FBI agent Bill Roemer visited Mabley and told him, "Dick Cain died a martyr, he was working for us." Mabley was clearly pleased to share this with me, but I was skeptical and could tell he wasn't exactly buying it either. He was trying to bring a measure of peace to a guy dealing with his brother's murder and he didn't think I was ready for the real truth. I asked him if he thought Dick had ever killed anyone.

"Well, yes, I suppose," he said, "but I'm certain he never killed anyone that didn't deserve it."

I was still skeptical of Dick's martyrdom, but still couldn't wait to share Mabley's comment with my father, thinking it would make him feel better.

"What the hell are you poking around in that mess for?" was his response. It seems my brother Bill had already told him what I'd been up to.

That was the last discussion J. B. and I had about the research that would consume parts of the next twenty years of my life. I would occasionally ask him questions about Dick to test the current climate, but he was steadfast in his refusal to discuss it, so I just carried on without his knowledge. Sometimes I felt a little guilty, especially as I got to know Lydia, J. B.'s first wife, but I always found ways to rationalize it. My one concession to his feelings was a private one — that I wouldn't publish the book until after his death — but that didn't apply to research.

I was transferred to California in 1974, and shortly thereafter Congress passed the Freedom of Information Act (FOIA). In the course of my work I'd gotten to know a freshman congressman from San Jose, Norman Y. Mineta, and asked if Norm would write to the FBI and the CIA on my behalf requesting a release of Dick's file. As it turned out, that wasn't the best strategic move. I was naïve and only just beginning to learn about research. Both agencies resented the passage of FOIA and generally didn't respond well to congressional requests because it had been Congress that foisted this burden on them in the first place. They eventually sent me about ten pages, 90 percent of which had been redacted. What was left convinced me that it was worth digging further. Over time I got better, and new laws aided my research. Eventually, I'd get nearly five thousand pages from the FBI alone.

At the time, though, the FBI reacted by making me a target. They began casually following me, and ultimately planted an agent inside the company I worked for to investigate me. On one occasion, an agent from the San Francisco office called me and asked for a meeting. He eventually admitted that he'd thought I was a member of organized crime and was hoping he could flip me as an informant. He didn't much appreciate my hearty laughter.

The inside guy represented himself as a former FBI agent and offered to help me get information, but I was to tell him what I knew. I became skeptical of his intentions when he suggested to me once that the FBI didn't like my digging around much, and they might scoop me up one day and take me "out to the rail yard and beat the crap out of me." He wondered what my reaction to that would be.

I was incredulous, and suggested that the only reason I could think of that they'd do such a thing was to cover some wrongdoing on their part. If that was the case, I was more determined than ever to proceed, and my guess would be that if they ever carried out this threat I'd be sure to sell ten to fifteen thousand more copies of this book. I told him I didn't think they'd be stupid enough to kill me, so they could bring it on; I'd take a beating for the additional sales. It wasn't long after that he left the company, never to be heard from again.

When Bill Roemer, a retired FBI agent, published his autobiography, Man Against the Mob, I wrote him a letter and thanked him for the kind things he'd said about Dick. Over time, Roemer and I became friends; he encouraged me to "keep punching," a favorite phrase of his that carried over from his boxing days at Notre Dame.

Along the way I've met some fascinating people. Good guys, bad guys, cops, and robbers. No one (except for the FBI) ever threatened me. I was cautioned to "be careful" more times than I can remember, but I never really felt unsafe.

I was constantly amazed at the impact Dick had on the people who knew him. I interviewed a federal judge, just for background, because I knew he had been a criminal defense attorney in the fifties and sixties. I wanted to get a sense of the times. It turns out that the judge had met Dick once, at the Playboy Club on Michigan Avenue in Chicago. He was having lunch with several colleagues when Dick walked up to say hello to George Callahan, another defense attorney at the table. As the judge told me, "George introduced him around the table and, of course, we all knew who he was. We were very impressed with his demeanor, his dress, everything about him." The judge went on to tell me the names of all six men at the table with him and what they'd had for lunch that day. From my perspective the amazing thing about that story is that more than forty years had passed since then and the judge could recall the minutest detail about meeting Dick Cain. I asked him what he'd had for lunch the following day, and he hadn't a clue.

Dick had a demeanor about him, a savoir-faire that people remembered for years. Even the people who hated him remembered him with the same clarity as the judge. There isn't any changing who Dick Cain was. He was many things to many people, and always a master manipulator, a gangster, a crooked cop — but he was a truly interesting character.

The high drama of his public and private adventures was defined by his work as vice cop, international spy, bodyguard to presidential candidate Barry Goldwater, and Chief of the Special Investigations Unit for the Cook County Sheriff's Department. And that's just the beginning. He was also married and divorced four times, a made member of the Outfit (Chicago's version of the Mafia), and a convicted felon.


The Outfit. That's how they came to be known.

Al Capone hailed from Naples, as did his predecessor and first cousin, Johnny Torrio. When they arrived in New York they became gangsters, but they knew they could never become "made" members of the Mafia because they were not Sicilian. When they each, in turn, seized the opportunity to run things in Chicago, their rule was that all Italians could be members, not just Sicilians. Since they had never participated in the Sicilian ceremony for induction, they didn't know how it worked, so they just declared a guy to be made when they wanted it done. Over time, when the Sicilians attempted to wrest control from Capone, he'd simply have them killed and send word back to New York that he would kill them all if he had to. Eventually they got the message and Chicago stood on its own, answering to no one.

Dick Cain's story begins in the era of Al Capone, when Dick's grandfather, Ole Scully, lived and worked in Chicago. It was the best of times, and the worst of times.

In the fall of 1928, Herbert Hoover defeated Al Smith in the presidential race. From humble beginnings, Smith had worked hard and became a respected member of the New York Assembly and a four-time governor. Smith's presidential campaign had nearly put the country on end. He favored repeal of the Eighteenth Amendment, and many people were genuinely concerned that a Catholic president would run the White House as an extension of the Papacy. So real were voters' fears that four southern states recorded not a single vote for Al Smith, and Hoover was swept in by a margin of six million votes. Being Catholic hurt Al Smith at the polls. Being a Democrat cost him the election. In 1928, no Democratic candidate could have won.

In 1928, the stock market was booming and the voters were supportive of a government that sought most of its tax revenues from the rich. There were changes going on, though — farmland was losing value and the Great War had brought the boys off the farm. Many didn't want to return to the farms at the end of the war. They'd seen a new way of life and they wanted more of it. High school enrollment was up sixty-six percent, and college enrollment was up by more than seventy percent over pre-World War I enrollments. As a country, Americans were becoming better-educated and less willing to do the menial jobs they had left behind when they went off to fight the War to End all Wars. Household income, while having grown steadily, was less than $2,000 a year.


Excerpted from "The Tangled Web"
by .
Copyright © 2018 Michael J. Cain.
Excerpted by permission of Skyhorse Publishing.
All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.
Excerpts are provided by Dial-A-Book Inc. solely for the personal use of visitors to this web site.

Customer Reviews