Baa, Baa 'Black Sheep': A Chat About the Infamous Irwins

Compiling family history can be a fascinating pursuit, particularly when a living descendant bequeaths a story as colorful and riveting as that of brothers Tom and John Irwin. The young men, among my grandmother’s numerous first cousins, shared a cold-water flat in Manhattan’s gritty Hell’s Kitchen neighborhood. That was, until Tom was arrested with two other men in the Oct. 16, 1926, rape and armed robbery of Maxime and Helene Jolivette in a Hell’s Kitchen apartment. 

Above, a Hell's Kitchen scene, beneath the 9th Avenue elevated railroad line. Photo / Museum of the City of New York  

It is a quintessential New York crime saga, with an Irish twist, as the family had emigrated from County Cavan to New York City just prior to America's Civil War and moved to the Irish-dominated wharves-side enclave known as Hell's Kitchen, where they remained for generations. Interestingly, as recently as two years ago, an "Irwin gang," based in Sligo generated headlines in Irish newspa... accused of murder and other mayhem tied to their sale of illegal narcotics.

The rub here is that Tom maintained he was innocent, not remarkable in itself, of course, but what is startling is that he stated to authorities that his brother John, a.k.a. Yerkie, was among the perpetrators. My Dad, also named Gerald Regan, told me through the years, in various conversations, that the Irwin family believed Tom.

When Tom began his 20-40 year sentence in Sing Sing Prison in 1928, authorities duly noted in the prison receiving blotter that Tom stated "his brother committed the crime and blamed him as they look alike." The New York Times described Tom as Yerkie’s “Irish twin,” noting they were born 11 months apart. The men’s family was upset with Yerkie’s willingness to let Tom be the ‘fall guy.’ 

In 1931, three years into Tom’s sentence, Yerkie confessed his guilt to a New York State Supreme Court justice. Despite that public confession, revealed in a story in The New York Times, according to research to date, Tom was to serve at least another eight years in the slammer.

The following transcript represents a return to my initial primary source, that is, my Dad’s recollection of the Irwins’ startling story. In the decade before my Dad’s passing, I interviewed him on a number of occasions about the Irwins. This transcript, along with the actual audio provided here, represents the final interview with him on the topic.

The interview was conducted June 6, 2004, in the kitchen of my Dad's home, in Garden City, N.Y. He was 83 years at the time, and rather short-tempered during the interview as I pressed him for details. Our research suggests my Dad had an excellent recall of details he had heard mentioned. Most of what he passed along has proven accurate to date. My father died three years later, on June 1, 2007, at 86.

Ger: It’s June 6th, the 60th anniversary of D-Day. We’re sitting here in the TV Room in Casa Regan with the patriarch. I want to learn as much as I can in the next 15 minutes or so about the Irwins. Your grandmother Susan Condon -- her maiden name was Irwin --

Dad: Susan Irwin

Ger: That explains the role of the Irwins in the overall family history.

Dad: To my knowledge, she had three brothers, John, Willie and Frank. Frank was the only one that used to come out [to her house, across the street, in her home in Richmond Hill, Queens, N.Y.]. He seemed to be the most sensible of them all. He dressed very nattily. He had snow white hair, he was in his 60s.

Left, my great-grandmother Susan Condon nee Irwin, an aunt of Tom and Yerkie, circa 1920. We haven't yet found any pictures of the immediate Irwin family.

Ger: When was [Frank] in his 60s, [it was] in the ‘30s when you remember him?

Dad: Yes, I remember him. He was the only one that I had some recollection of. In the late ‘20s I don’t remember the exact time. He had Irish pink skin, pink complexion, white hair, and he was soft-spoken. He seemed to be a natty dresser. The other two I have only vague recollections of them being a couple of slobs.

Ger: Any idea of what Frank did for a living? Was he retired?

Dad: I have no idea. Willie and John were a little eccentric. Grandma [Condon] would have them out and they’d probably stay a day or so with her.

Ger: Would they come out together -- Willie and John?

Dad: No, she didn’t have room to put the both of them up at once. And my recollection was to go over and see Grandma, and the uncles were sitting there, one in his underwear and the other would be out taking a walk.

Ger: Which one would be wearing his long johns?

Dad: I think it was John, he had a derby hat on and be sitting at the kitchen table.

Ger: Would he be smoking. Smoking a cigar?

Dad: I don’t know if he’d have been smoking. Gerry, you’re talking about 70 years ago, 73 years ago. I don’t know if my grandmother allowed smoking in the house.

Ger: Did she smoke . . . Susan?

Dad: No, no women in her generation smoked. It’s [in] the next generation women found it fashionable to smoke. They didn’t know how to smoke, but they smoked.

Ger: Your mother smoked, I remember.

Dad: She didn’t know how to smoke, but she smoked.

Ger: For how many years?

Left, my Dad, Jerry Regan, in his easy chair at home in Garden City, N.Y., where he would hold forth on many aspects of world affairs and our colorful family history. Regan Family Archives, 2003

Dad: Not too long. I don’t know. I don’t know when she started and don’t know when she stopped. But she became an avid anti-smoker, waving her finger at those who smoked.

Ger: So your recollections were that even though [John and Willie] might not have stayed overnight, they would have been together in the kitchen?

Dad: I don’t remember seeing them together at different times. Frank was the one I saw the most. I don’t remember Willie or John ever being in our house. ... But Frank was.

Ger: Any idea where they lived?

Dad: On the west side of New York, probably in the tenements.

Ger: Hell’s Kitchen, you think?

Dad: That’s where they all came from. You have to remember (that), before rapid transportation and buses and telephones and all that, coming out to Long Island was a tremendous voyage for them.

Ger: Any idea how they would come out? Would they take a car or a cab?

Dad: No, they probably were never in a car in their lives. They took the train. The station was on the corner. That was the elevated line.

Ger: Were these gentlemen married?

Dad: Frank was married. I don’t know about the other two. I never saw any wife with any of the three of them. Frank’s wife must have died. I don’t know. Again, I keep emphasizing I was a very young boy and I frankly didn’t give a damn about any of them, whether they were there or not.

Ger: Was your mother fond of them, Frank and Willie and John?

Dad: Not overly. They were characters, Willie and John. You don’t fall in love with characters. You tolerate them.

Ger: Were they boozers? Did you have a sense that they were boozers?

Dad: I never saw them doing anything but sitting at the kitchen table during the day. I never saw them at night. I never saw them in a bar.

Ger: Was Susan Condon, your grandmother, much of a drinker?

Dad: I never saw her take a drink in my lifetime. I was 14 when she died so I wasn’t privy to what her social life was. She had none.

Ger: Her husband, John Henry [Condon], your grandfather, was apparently a heavy drinker, he had cirrhosis of the liver.

Dad: He probably was a boozer and a carouser, but no one ever talked about it. “Pappa died of complications” [was a common explanation].

Ger: Now the other story you’ve told and that I’ve enjoyed is your recollection of some kind of sordid crime by two of Frank’s sons, Tommy and Yerkie, or one of the two. Can you just relate that story, as you remember it

Dad: All I know is that I was about 11 years old and I heard that Frank Irwin’s son was in Sing Sing. But the other side of the story was he didn’t commit the crime, his brother did. But his brother wouldn’t turn himself in, and he let Tommy Irwin get sentenced to 40 years in prison. And they tried to prevail upon him to go and turn himself in, but he wouldn’t do it. So apparently even the neighborhood police knew that he did it, but they nailed Tommy.

Ger: What was the crime?

Right, old cell block, Sing Sing Prison, 1938 / World Telegram Photo by C.M. Stieglitz, Library of Congress Prints and Photographs Division. New York World-Telegram and the Sun Newspaper Photograph Collection. http://hdl.loc.gov/loc.pnp/cph.3c19802

Dad: It was supposed to be rape and stealing a woman’s diamond ring.

Ger: And he raped her, as well?

Dad: The crime was rape, and he stole a ring. I don’t know whether it was grand theft or petty larceny. It might have been a five-and-dime-store ring. I don’t know. No one ever told me anything. Hearsay, hearing my father talking, my mother talking.

Ger: They would usually send you out with money to go out and play when they were talking?

Dad: Not with money, they wouldn’t send me out with money. [They’d say] “Why don’t you go out and play with the kids?” And then they’d have a serious conversation. I imagine that would be the idea, of getting us out of there.

Ger: They’d send your brother out with you or would you go out separately?

Dad: I don’t ever remember us two being involved at the same time.

Ger: Then there’s another story you’ve told, about going to Frank Irwin’s funeral or wake and, apparently, seeing either Tommy or Yerkie,

Dad: It was Tommy was brought down from Sing Sing with a black prison suit on and a black hat and handcuffed to two burly detectives brought into the funeral parlor.

Ger: Was it a regular suit of clothes?

Dad: It was a regular suit of clothes. It was what they issued you probably when you were released. …

Ger: On compassionate leave? He was reasonably well-dressed?

Dad: He was dressed in a suit. I wouldn’t call it Wallach’s or anything.

Ger: You recall him wearing a hat, too?

Dad: I never saw him without a hat. He had the hat on all the time he was there.

Ger: Like a fedora?

Dad: Yea, that’s the only type of hats they wore. Maybe it was his own clothes. Jimmy Cagney always wore his own clothes to Sing Sing [as portrayed in his various gangster films].

Ger: I guess that’s the last time you heard of the Irwins mentioned?

Dad: I guess there were dribs of something over the years. He went back to prison. I don’t know if he died in prison or ever got paroled.

Ger: He never came looking for a job? He’s one of the few people who never hit you up for a job.

Dad: Yerkie and Tommy would be about 110 years old if they were alive.

Ger: Do you have any cousins from the Irwin’s side of the family?

Dad: I never met any. I never met an Irwin other than those three. I don’t think Willie and John had any children. And Frank had two that I know of. He may have had others, but I never met them.

Ger: So that would be the end of the line?

Dad: My mother used to say there was an Irwin that lived in Floral Park [N.Y.] She thought they were related, but she never did anything about looking them up or anything.

Ger: [Perhaps] one of Tommy or Yerkie’s chldren, presuming they went on to have any children? [We now know the Irwin brothers had three children, collectively, at the time of the attack on the Jolivets.]

Dad: I don’t know who they were. She used to talk about a cousin or a relative that lived in Floral Park. She never looked them up, never met them. I never saw them.

Ger: Maybe they are still there. I’ll have to crack open a Nassau phone book and see if there’s still an Irwin in Floral Park.

Dad: They probably don’t know that we exist.

Ger: Yes, the Irwins are an intriguing crew.

Dad: You have to understand they were all first- or second-generation Irish living in poverty over on the West Side of New York, living and dying in rat-infested tenements. And they never broke out of that life. As far as I know. The Condons [on the other hand] ... John had a fairly good job in the warehouse, and he moved the family to the Bronx. So they got out of the West Side of New York. But that’s where they are all from.

Ger: You had mentioned at one time that either Tommy or Yerkie had a newsstand?

Dad: Again the story … Yerkie had a newsstand on 34th Street. And people used to stop by and try to prevail upon him to turn himself in, and he probably said: “Screw you. I’m free. Let him [Tommy] stay there.”

Left, a typical midtown newsstand, perhaps a place where Yerkie might avoid, for a time, the family's wrath. This one was located at 35th Street and 3rd Avenue. Photo by Berenice Abbott, 1935, Changing New York, Federal Art Project, WPA/The New York Public Library.

Ger: You think Frank might have been a watchman somewhere?

Dad: He might have worked for the city. I have no idea. He didn’t come and tell us kids that “Uncle Frank is a success at this.” They were all menial jobs. Half of them were probably on welfare. I would say it’s just a true pattern of the Irish-American second generation in this country. They never got out of poverty. They had no schooling. They all dropped out of grammar school.

Ger: I guess you have no idea whether they could read and write, the Irwin men?

Dad: They never wrote me a letter. You have to look up on the history books whatever you want to call it, a lost generation. And some rose out of it, like [former New York Governor and Democratic presidential candidate] Al Smith, to become pretty famous people. Jim Farley, people like that that made something of themselves. The rank and file and I don’t know anyone in that side of the family or on the other side that was ever successful. The most successful part of both sides of the family was my brother and his eight children, and they were all well-educated and have good careers and jobs and families. But that’s a whole other chapter.  

Ger: One of the cousins last night made a reference to an anecdote that your father would share with them about Uncle Willie apparently either being the butt of a practical joke or being the practical joker himself and putting limburger cheese in [a derby worn by one of the eccentric brothers] …

Dad: To my knowledge, neither Willie or John were capable of practical jokes. They were dimwitted. So maybe the joke was on them. Probably people baited them and teased them and made fools out of them. I don’t see them being smart enough to pull practical jokes on anyone.

Ger: Alright, thanks, Dad.

Views: 193

Tags: Crime, Family History, Justice, Punishment, Urban history, black sheep

Comment by Claire Fullerton on January 31, 2017 at 5:45pm

Oh my goodness! I think this is the best dialogue I've ever read! I could just feel your father's character. Two things stood out for me whilst reading this: his use of the word prevail, and the many, many snappy come-backs. A man has to be on his intellectual toes to sport this kind of humor!  When you asked if the Irwin boys could read and write, the response," They never wrote me a letter" saw me LOL!   I think I have a crush on your father!

Comment by John Anthony Brennan on January 31, 2017 at 5:46pm

A fascinating story of a time gone by. It reminded me of the old adage, "there must always be a scapegoat."

No brotherly love there....!! Did they ever find the truth?


Heritage Partner
Comment by That's Just How It Was on February 1, 2017 at 6:29am

Oh Gerry..... what a wonderful chit-chat.. I love the dry humor of you Dad... I think a lot of Irish have that dry humour......  I love the way in which the , the conversation is so witty and real , that I cab hear myself talking to my grand-mother and my mother .. Both had a dry sense of humour, while other people thought they were hilarious, they never could understand why people were laughing. ....

OH Gerry, this woudl make a  wonderful stage play... The  Da and me [Da being what Dubliners call Dad ] 

There were tears running down my face reading this, nostalgic... and the fact that it is so true to life ... Wonderful ..

Comment by Claire Fullerton on February 1, 2017 at 9:38am

Just want to add here that I agree with the above comment, and it occurs to me that this well-written piece brought something important to mind: Our Mr. Brennan, of course, went right to the "story," which is engaging and thought-provoking, and yes, readers want to know if the Irwin brother who was wronged was ever vindicated. But the way the dialogue is written here ignited something within me I've long been guilty of: If I find the story teller fascinating, I am so busy studying his mannerisms that the story is almost incidental. Not to suggest the story is incidental here, but, for me, it took a back seat to the way your father "prevailed" upon it! 

Comment by The Wild Geese on February 2, 2017 at 10:46am
Claire,John, Mary, thank you all for the feedback. My Dad was a natural-born raconteur. Funny, as the saying goes, he got a lot smarter as I got older. Luckily, I didn't wait till he was elderly to come to relish his love and wisdom and experience. I've embedded a number of interviews with him in my posts, as they became the basis of those stories. I'll produce more in the months to come.
Comment by Claire Fullerton on February 2, 2017 at 11:07am

You are a lucky man, Ger, and we all have the benefit of reveling in your good fortune, for you are a gifted story-teller, wise and big-hearted enough to share! Slainte, my friend!


Heritage Partner
Comment by That's Just How It Was on February 2, 2017 at 11:47am

Ger, you are indeed very fortunate  to have had all this chit-chat with your Dad.. My Dad did not get to grow old , fortunate,, and my husband did not grow old to have those discussion with his children,... Treasure all those memories Ger ... they are worth more than gold !! 

And I will look forward to the next installment of  ' 'The Da'  and again I say.. it would make a wonderful Irish historical play .. The  language was spot on ... witty, funny, had me in stitches .... 


Founding Member
Comment by John M. Walsh on February 2, 2017 at 6:50pm

Dad is brutally honest, that is to say, he does not invent alternative facts to create a colorful, detail-rich narrative.  Your father was content to leave the story telling to the novelists and script writers.  Thank God for the truth tellers, and thank God, also, for the imaginations which create the novels I love to read.

Comment by Gerry Regan on February 3, 2017 at 1:28pm

John, thanks for taking the time to comment. My Dad was a remarkable man, fully representative of the best of 'The Greatest Generation.' Here are a couple of other posts that depend on my Dad's unvarnished speaking style for their storytelling power: A Sailor in Wartime Dixie: Startled by Catholic Apartheid‘We Will Probably Land Christmas Day’: At War in the Atlantic, 1942‘3 More Shopping Days Left': A Christmas in Convoy 1942

Perhaps my favorite interview with my Dad is this one, for both my Dad's honest telling and colorful turne of phrase: ‘Who Turned Those Lights On? Kill the B------’: Christmas at Sea 1942

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