My sisters, left to right, Gloria O'Grady, Marguerite O'Grady Becker and friend celebrating VE day. They did all the talking. I did all the eavesdropping. (Photo courtesy Mary Kay O'Grady)

This is longer than our usual Viewpoints essay, but it’s August and it’s a fascinating read:

My parents seldom talked about family history, but my older sisters did. I used to eavesdrop on my sisters telling stories about various relatives. They’d say “That’s rich,” which I took to mean funny with a dash of buffoonery. Later on it hit me that many of the stories involved crime.

My four grandparents were born in Ireland in the early 1860s and immigrated to the United States. I can’t trace their arrival in the U.S., but they all eventually lived and died in Chicago. They had scads of children. My maternal grandmother, Kathryn Rooney Russell, gave birth to 11 children, three of whom died in infancy or childhood. I was told she was at the Haymarket riot with a child in her arms. My paternal grandmother, Mary Hastings O’Grady, had at least seven children. My father was the baby of his family, born in 1901. My mother, the 10th of 11 children, was born in 1900. I was the baby in my family, born in 1940 when my sisters were 6, 14 and 15.

I occasionally told my own kids some of the stories, probably because the Irish love a good story, but I really never thought of my forbears as criminals. I wonder if it’s the same for children and grandchildren of, say, Mafioso. Now my grown children, my sister’s children, and the grandchildren are asking lots of questions, and I have become the primary source.

‘Auntie Bridget went to Mass’

I joined when my niece’s son wanted to know who was the one in my family who had contributed to the I.R.A. It was my mother’s sister, my Aunt Lill (there were not one, but two Lillian Russells in the family — my mother’s sister and her sister-in-law).

The I.R.A. aunt was a tall, buxom, single woman, very religious, who worked for the CTA and kept her hair strawberry blonde well into her 80s. The other Aunt Lillian was married to my Uncle Dick, my mother’s twin, who is said to have shot his wife’s first husband in a bar in Indiana. It is worth noting that as I examined census reports from 1910 onward, several uncles listed my grandparents’ country of origin as the Irish Free State, so they probably supported the I.R.A. too.

This past season the HBO show Boardwalk Empire, in an episode about the rise of Al Capone, referred to my mother’s cousin, Spike O’Donnell, as the boss who controlled all of the South Side during Prohibition. My mother used to enjoy playing at the O’Donnell house when she was growing up. However, whenever Spike’s name came up at family gatherings, my mother and my aunts would simply say, “Auntie Bridget went to Mass every day of her life.”

I can see why. Spike came from a family of nine children, four of whom were part of a notorious gang. My father once told me that when Spike died — a natural death, unlike two of his brothers — the number of bullet scars on his body was noted by the newspapers. He is said to have survived an attack by the very first tommy gun (Thompson Submachine Gun) used by an upstart who shot up the whole corner of 63rd and Western, but missed his assignment.

Spike was well traveled and “well-testified,” at congressional hearings, inquests, etc.  Celebrities loved to hang with gangsters in those days. There’s even a tape of himself, dapper as hell, giving advice on how to help young people avoid a life of crime: education and keeping young criminals separated from hardened criminals in jail. When Spike died, Spencer Tracy and Humphrey Bogart attended his funeral. Bogart was said to be terrified of him.

‘That’s my father. We all hate him.’

The O’Gradys were what is called Black Irish, but it wasn’t only their pale skin, dark hair and dark eyes. The men seemed to suffer from melancholia and antisocial behavior; the women were, I think, beautiful, strong and humorless.

I admire my Grandma O’Grady — who died before I was born — for her courage. She was born about 1861 and came to this country when she was only 15. She got a job, presumably as a maid or seamstress, and saved enough money to bring her four sisters, Kate, Nora, Delia and Anne, to the states. The sisters had vowed as children that they would never be separated again, and they all married and lived within blocks of each other in Chicago. Two of the sisters married brothers by the name of Sweeney.

Then there was my Grandfather O’Grady. He is listed as a hod carrier on early records and later owned a vegetable stand, kitty-corner from Holy Name Cathedral. When my mother was dating my father, he once pointed out a man across the street and said, “That’s my father. Don’t talk to him. We all hate him.” A girlfriend of hers told her not to marry one of the O’Gradys. “They’re always fighting. One of them threw a Thanksgiving ham across the table at another.”

Before I discuss crime in the family, I should point out that two of my O’Grady aunts, Mary and Margaret, were beautiful. My Aunt Mary was engaged to Martin Kennelly, who preceded the first Mayor Daley in office. She died of scarlet fever before they married, and he remained single all his life. My Aunt Margaret married a divorced(!) lawyer, sent her daughter to boarding school, and wound up living on Lake Shore Drive.

I don’t know much about my Aunt Nora, the oldest girl, except that she had a baby out of wedlock, who was raised by her brother Will, the uncle who was a policeman. That baby later became my godfather. Nora died in an insane asylum. Along with my unanswered questions, I feel an intense grief for what happened to her in the early part of the century.

I believe the oldest child in my father’s family was Francis, but my mother always said that wasn’t his real name. (Immigrants often changed their real names so they didn’t sound too Irish: One uncle, whose name was Patrick, became Richard and an aunt whose name was Johanna became Josephine.) Francis was a large, strong, jovial man who started his career in crime by stealing a boxcar of shoes in World War I. In France.

Think about it. How exactly did he pull that off? I think that’s worthy of Butch and Sundance. For his efforts, Francis did time in a federal penitentiary.

We all loved Francis, except my father, who dreaded phone calls from him, knowing it meant trouble. I presume my Uncle Will, the police officer, either gave up on Francis, or could only put in so many fixes. Whenever Francis came to our house he brought exotic things like garlicky food and gifts for my mom: sterling silver and china. I was looking at a silver pitcher once and I asked her what the engraving CBH meant. She answered that Francis had once worked at the Chicago Beach Hotel.

Recently I’ve been looking at some of the pieces that were my mother’s. For instance, I have about 10 odd pieces of china that we used when I was growing up. (I often wondered why we had such nice china if we were so poor.) Some of the pieces are marked The Stratford, which turns out to be what is now called the Belden-Stratford Hotel in Chicago. Apparently Francis worked there, too.

We didn’t see him much, but whenever he called, usually at night, my dad would have to go out, would get back late, and be angry. In my research, I found that Francis also enlisted in World War II at the age of 51. Apparently older men (another uncle was 62), including George Halas and Cardinal Stritch, were allowed to sign up for what was called the “Old Man’s Draft,” which targeted older men not for military service but for disaster relief on the homefront, should worse come to worst. Francis’ enlistment form contained a space below his name and address for a “person who will always know your address.” Francis listed (add Irish name here) of the Chicago Police Department.

Seriously, isn’t that rich?

Francis gave me a gold watch for my college graduation. A few years later, I mentioned to my parents that the watch wasn’t working and I was going to take it to the jeweler’s for repair. My father said, “I wouldn’t do that if I were you.”

When Francis died, my mother and I went to a bank in the old neighborhood to open his safety deposit box. Inside were a wedding ring and a gun. We looked at each other and shrugged.

Goons in the foyer and a walk along the tracks

My father, Edward O’Grady, born in 1901, only completed eighth grade, but I’m not sure why. Since he was the baby of the family, there should have been enough siblings working that he would not have had to go to work. I know by census reports from 1920 that he no longer lived at home, so he must have been in San Francisco by the age of 19, where he became a telegraph operator. He was back in Chicago by 1923 when he and my mother were married. I know my mother married him because she thought he was smart. I also know he was a gambler and made and lost a lot of money and that the Depression was devastating. Whenever I play cards with my grandson, he loves the story that my father was playing Hearts once when one player stood up and shot another.

By the time I was born in 1940, my dad was working for James Ragen on a legal daily racing sheet, one of those created after the government cracked down on mob-controlled racing wire services.

Ragen got his start when he and one of his brothers founded the awful Ragen’s Colts, a so-called “Irish athletic club” — the first Mayor Daley also ran one — which flourished in the Irish Back of the Yards neighborhood. Ragen’s Colts fought the anti-Catholic Ku Klux Klan but also instigated the worst race riots Chicago had ever seen, resulting in many deaths. The Colts terrorized Chicago’s African-American population for more than a decade. In 1926, a group of Colts lured a black man behind their headquarters, then stabbed him and shot him dead. Wednesday Journal would probably love to exercise the journalistic candor of the following day’s Tribune headline: “Four Morons Kill Negro at Ragen Colts’ Hangout.”

After Ragen’s Colts disbanded, Ragen started the very successful racing sheet that would eventually become the Illinois Sports News (Green Sheet). The mob wanted in. Ragen became involved with Moe Annenberg and Al Capone and was pressured by Tony Accardo, Murray Humphreys and Jake Guzik. After it became public that Ragen had been interrogated by the U.S. attorney general, Ragen was shot down by a Capone gang member in 1946.

Ragen let it be known to columnist Drew Pearson (everybody liked to hang out with gangsters in those days) that if he died he had written info on the mob. While he was recovering at Michael Reese Hospital, Ragen signed an affidavit identifying his attacker.

Ragen was well on his way to recovery, when he died suddenly following a mysteriously administered dose of mercury. The affidavit was “lost” and the state’s attorney was unable to prosecute those named by Ragen.

Here’s where my father comes in. My father was a favorite of Ragen, probably because he was an excellent handicapper. I remember that we all had to be quiet in the evenings when my father was “working,” with several racing forms spread out on the dining room table.

It turns out that my dad visited Ragen in the hospital and was apparently the last person to see him alive, though that seems strange since there was all sorts of security around Ragen. On the other hand, I overheard my father say that a friend of his who was in protective police custody was thrown out the window by the police.

After Ragen’s death when my dad came home from work, there would be a couple of guys in the hallway to our apartment building. They just stared at him but said nothing. I was six at the time, probably upstairs waiting for my dad to come home so we could listen to The Lone Ranger together.

Around that time, my dad took my mom for a walk along the Rock Island railroad tracks near 89th and Ashland, so no one would overhear their conversation. He told her that he had a chance to make a lot of money, but it would be dangerous. Apparently they decided against it although we got a car and moved to the suburbs within a few years.

Ragen’s racing paper, the Illinois Sports News, was bought by Tom Kelly, who was called to testify in 1950 by the Kefauver Committee (the U.S. Senate Special Committee to Investigate Crime in Interstate Commerce.) He temporarily made my dad the company’s treasurer and sent him to testify. I was in fifth grade. My mother made me stay home from school. The next day, my dad’s picture was in the Tribune, and I thought he looked quite handsome. Black hair, black overcoat, black Irish. If my friends or their parents noticed it, no one ever said anything to me. I still have work to do in newspaper archives to find that picture.

My dad worked at the Green Sheet until his death at the age of 73. He was considered the best horse handicapper in Chicago, and he fumed when one of the major paper’s handicappers stole his stuff. He put me through college by walking to the La Salle Street station every day and making a call on a public phone giving racing information to … who knows?

On a personal level, I hope to God that my father was not in Ragen’s Colts. I think I would have heard if he was. I would find it hard to believe that my father killed James Ragen. My dad was polite, often jovial, religious — well, he went to church every day — and prudish. Still …

I think the uneducated Irish had the value of speaking English, had access to pretty good Catholic schools, and were willing to escape miserable lives working in the stockyards by turning to crime and eventually politics. I think my father did whatever he had to do. Given that two of his four daughters were seriously ill, I’m guessing my immigrant grandparents would be amazed that I graduated from college, got a master’s degree and did graduate work  at Harvard.

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Mary Kay O'Grady

Mary Kay O'Grady is a former high school English teacher and later owned her own public relations business, The O'Grady Group. She has lived in Oak Park for almost fifteen years. She is currently the chairperson...

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