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Davy the Punk by Bob Bossin  

Celebrated Canadian folk singer Bob Bossin tells the story of his father’s life in the gambling underworld of the 1930s and 40s. By turns a touching memoir of father and son and an insightful social history, Davy the Punk is packed with street-wise stories and troubling revelations about Canada in the 20th century.

In the first half of the 20th century, Toronto prided itself on being ‘Toronto the Good’. But Davy the Punk’s Toronto was tantalizingly bad.

In the 1930s Davy Bossin was known in the gambling underworld as ‘Davy the Punk’. He was the city’s top layoff man, the ‘bookies’ bookie’ who connected Toronto to the continental betting racket. Later he ran the Toronto terminus of the notorious race wire, the underground information network essential to the gambling industry. By the 1940s, that put Davy in the crosshairs of the law’s efforts to quash organized crime.

To see Davy Bossin, you would never have guessed it. Outwardly, he was so taciturn that some thought him mute. (‘What you don’t say can’t be used against you,’ he taught his son.) But at the right time, among ‘right’ guys, Davy was a consummate storyteller, regaling his pals with outrageous tales of horse-race gambling, the mob and the underside of show biz. Eagerly taking it all in was his son, Bobby, who would grow up to be Canadian indie music pioneer Bob Bossin, a revered storyteller in his own right.

Now 70 years after his father’s precedent-setting legal battle, Bob tells the story of Davy the Punk. By turns funny, maddening, insightful and moving, it is both a memoir of father and son and an eye-opening reconsideration of law-breakers and lawmen, of the Great Migration, and of the distressingly anti-Semitic Canada left out of the history books.

For more information on the musical, visit


2015—Heritage Toronto Awards,


2016—Western Canada Jewish Book Award,


2016—Vine Awards for Canadian Jewish Literature,

Review text

Deftly organized for maximum enjoyment and insight, this memoir brings to life important times in Jewish Canadian history.

Bob Bossin’s memoir about his father, Davy the Punk, is an enticing, engrossing, and enchanting read. Bossin’s father died when he was ten, so Bossin needed to stretch the structure of his book and create much more than a memoir. It is Jewish genealogy (Bossin’s family emigrated from the Ukraine in the late 1880s), it is Canadian history (they settled in the slums of Toronto), and it is a commentary on both Canadian and American social problems (primarily gambling on horse races and bootlegging in the decades prior to World War II).

Since Bossin has direct knowledge of his father for only ten years, he has had to verify many of stories he heard as a child. In the afterword, he details the painstaking research he attempted for years; this section by itself is a superb reminder to memoir writers that the best stories get the facts straight.

Bossin’s background as a journalist serves him admirably. His prose is lively, and the memoir has the intrigue of a novel. The title is a reference to his father’s alleged association with gangsters. The author’s style is folksy, and he often clutches a cliché and squeezes out extra metaphorical meaning: "The streets of the Ward were not paved with gold, but they were paved." Sometimes he uses a common phrase in an uncommon context, giving it new life; Bossin scorns the Volstead Act and comments that it "offered the greatest affirmative action program for criminals ever devised." His proficiency in writing is evident when his father retells one of the more famous jokes about race horses, the saga of Lucky Seven.

The vintage photographs bestow the feeling of nostalgia and are strategically placed throughout the memoir rather than incorporating them all in a separate section. This positioning serves to comment on and strengthen the narrative. Bossin characterizes Senator Estes Kefauver as less than stellar, for instance, and the accompanying photo portrays him as a dolt from Tennessee.

Readers interested in Jewish culture in Canada, the inner workings of gambling on horses, or just a bittersweet yarn of a son admiring his father will relish Bossin’s story.

—Thomas H. Brennan, Foreword Reviews

Review quote

‘By parts history, anthropology, political science, biography and memoir, the book follows Bob’s father, his family, the circles of his underworld and, later, show business associates, and a great deal more.... "The personal is political," as the feminist adage teaches us. Here, the political is personal. The events of Davy’s time, roughly the first two-thirds of the twentieth century, rocked his life and career. Thanks to his son’s research and insight, we can learn a lot about those politics and their legacy by reading his engaging story. It’s this interweaving of political and personal that gives the book its strength and momentum. Each step on the narrative journey is supported with a wealth of background and analysis, always informative, always entertaining. Horse-racing stories and jokes are some of the best around, and the Bossins, father and son, tell them masterfully.’

—Stephen Aberle, Outlook Magazine

Review quote

‘Davy the Punk is a wonderful read on so many levels. Horse players will be thrilled at the old school tales of how races were bet and the shenanigans that took place to affect the outcomes. Historians will enjoy the walk through the first 50 years of the 20th century. And for those who are easily moved by father-son emotions, there’s plenty of that as well, including, late in the book, a stunning revelation about Bob Bossin’s own pedigree.

‘Bossin tells us that his father was a great story teller. Davy the Punk would be pleased to know he has successfully passed on at least one of his formidable skills.’

—Down the Stretch Newspaper

Excerpt from book

1. The best way to not get hit by a baseball

It is the summer of 1956 and I am sitting with my father, Davy Bossin, in the bleachers above first base in Maple Leaf Stadium, the old ballpark on the shore of Lake Ontario. Summer nights in Toronto are as humid as a Georgia swamp, and the stadium on the waterfront has been dubbed "the poor man’s air conditioning". Davy is sitting in the comforting breeze off the lake, reading the newspaper. I am giving him a fervent play-by-play of the game between the Maple Leafs and the Havana Sugar Kings. I am ten.

Through the early innings, we are joined by one, then another of my father’s cronies, who gather in the evening air to swap stories, argue politics, and only incidentally watch baseball. By my father’s decree, my colour commentary stops when the friends show up. This is fine with me; I love hearing the men talk the way they do when they are away from their work and their wives. I make myself as small as I can, hoping that my presence will be forgotten and I will overhear some secret that would otherwise be withheld until I have been dispatched for peanuts or hot dogs. Toronto was known, in those days, as Toronto the Good, but the Toronto these men recall is tantalizingly bad.

"Did you see Benny Kaufman died?"

"Benny the Shoykhet? With the little butcher shop in the alley off Kensington?"

"Yeah, exactly. Benny’s gone, alev ha-sholem."

"Did he ever get pinched? I don’t think he ever got pinched. He had a hell of an operation. You could make a bet, have a drink and buy a chicken."

"Did he actually sell the chickens?"

"Sure he did. They were good kosher chickens. Of course he always kept a few in the back in case of a raid. He had one of the kids out at the street, who’d whistle if the cop turned into the alley. Then the bubba would come downstairs and they’d stick the bottles in her apron and throw a couple chickens on top, and she’d shuffle down the alley, smiling and nodding at the cop. Benny stuffed his betting slips up the ass of one of the chickens. They never caught him."

"Yeah, they did. Herbie Thurston pinched him. Remember, Harry Thurston’s boy who became a cop."

"Nah, you’re all mixed up. Herbie never pinched Benny; the guy he pinched was Murray the Rug."

"In the old dry cleaner’s on Dovercourt!"

"Exactly. When he was a kid, Herbie used to go in with his father, when the old man placed his bets. Then when he became a cop, he went to Murray, and he told him, ‘Murray, I’m a policeman now and I’ll arrest you if I have to. You’ve done well, it’s time you retired.’ Of course Murray didn’t listen. He looked at Herbie, and saw the little pisher tagging after his old man. And nobody had ever been able to charge him, because they could never find his slips. But Herbie knew from his father that Murray kept them under his toupee. So he nailed him."

The stories go back and forth, of this bookie who got busted, of that one who never did. My father sits there reading his newspaper. The conversation flows by him, like water around a rock.

"What was the name of the guy ... the one they arrested over and over?"

Silence. Nobody remembers. Then a new voice says, "Shnooky Schneider. It was Shnooky Schneider." The voice is my father’s.

When Davy speaks, it is as if he were a king. Heads turn. This is because he speaks so rarely. And because, when he does, he is a natural-born story-teller. He folds his paper, none too quickly, and begins to recount how Arnie the Shnook Schneider was busted for book-making sixty-seven times, every one a first offence.

"In those days Arnie was working for Manny Feder," my father begins quietly, "back when Manny and his brothers had the big horse room on Queen Street, before they opened the Brown Derby. It was a pretty smooth operation, as it oughta be, since Manny had half the cops in town on the pad."

"But every now and then, the heat would be on. Old Reverend Domm would get up in Bathurst Street Church and preach a fire-and-brimstone sermon on vice, and then Holy Joe Atkinson would publish the whole damn thing in the Star: ‘Sunday morning, in Bathurst Street United Church, the Reverend Gordon Domm warned of the wave of corruption loosed on the city by gambling racketeers.’"

My father gives the Star the voice of Walter Winchell. As the plot heats up, so does his delivery.

"Then they’d send some cub reporter down Queen Street to lay some bets at some of the bookie joints, as if that was news to anybody, and they’d run that on the front page. And that would get the Decent Citizens riled up, and they’d start demanding that the police do something.

"So the cops would call Manny and say, ‘Sorry, Mr. Feder, but we’re gonna have to raid.’ And they’d tell him when. Then Manny would call Shnooky and tell him to get ready."

Here my father pauses, pretending to some interest in what is happening on the field. The men around me wait for him to go on. It seems to me all Maple Leaf Stadium does.

"Manny’s joint was on the second floor and it would be going full blast with punters betting, smoking their cigars, the phone ringing, odds coming in and getting chalked up, the loudspeaker blaring—‘They’re at the post. And they’re off...’

"But upstairs, on the third floor, there was another room with just a table, an unconnected phone and a folding chair. And that’s where Shnooky would wait for the cops. They’d come charging in, up the stairs, past the horse room, straight to the third floor. They’d arrest Shnooky and grab the telephone, so they could report that ‘gambling equipment was seized.’ Then they’d go back downstairs, past the horse room again, and take Shnooky to the station, where Manny would be waiting with Shnooky’s bail. Then, when Shnooky was convicted, Manny would pay the fine, which was, by standing agreement, a hundred bucks. It was like a tax.

"Of course the law said that, on a third conviction, bookmakers go to jail. But the cops would misplace Shnooky’s priors, or the magistrate would be one of Manny’s customers, or both. So every time, it went down as Shnooky’s first offence. And the government got its hundred bucks, which was good money in those days."

Sometimes the laughter from our section was so raucous the pitcher would turn and look up.

Unpublished endorsement

‘"I come from a family of storytellers," writes Bob Bossin, and he has clearly inherited the gift. A rich mix of stories about his father, his family, Jewish immigrant life, political high life and the criminal underworld. Entertaining, illuminating and, at times, touching.

—Leon Rosselson, author of Home is a Place Called Nowhere and Rosa’s Singing Grandfather

Unpublished endorsement

Davy the Punk spins his tales tall and true to the circl‘e of Jewish hoods in 1940s Toronto, mesmerizing them and us. In this memoir of a childhood that is the stuff of dreams and movies, Bob Bossin pays loving tribute to a father whose name alone conjures up a lost world. With a songwriter’s ear, a performer’s sense of timing and a poet’s grace, he brings that world back to life. The apple (or, in this case, the apple strudel) doesn’t fall far from the tree. ’

—Si Kahn, author, musician and organizer

Unpublished endorsement

‘I loved this. This generation [Bossin] writes about has now vanished, but the colourful, hard-talking comedic experience of life on the edge comes back. Bossin is a great storyteller, and these are great stories. I can hear the voice of that generation clearly. Wonderful!’

—Clayton Ruby

Unpublished endorsement

‘Damon Runyon meets Sholem Aleichem where the Orange Order calls all the shots. Davy the Punk is a touching and very funny portrait of a part of Jewish Toronto that too many people like to pretend wasn’t there.’

—Michael Wex, author of Born to Kvetch

Unpublished endorsement

Davy the Punk is a thoroughly enjoyable and revealing romp through the historical underside of Toronto the Good. With verve and enthusiasm, Bob Bossin brings a performer’s skill to the tall but true tales in what is, ultimately, his family’s story.

—Lilian Nattel, author of Web of Angels and The River Midnight

Unpublished endorsement

‘Bob Bossin’s father Davy lived in the seamy underside of Toronto the Good between the wars--a Runyonesque milieu of bookies and baseball, horses and payoffs, right in the zone where crime buys a drink for enterprise. Bossin’s memoir of Davy is fascinating, funny, dark and poignant--a vividly readable portrait of an unforgettable man in a remarkable habitat.’

—Silver Donald Cameron, author of The Education of Everett Richardson and The Living Beach

Unpublished endorsement

‘Amid the fascinating and sometimes belly-laugh-funny anecdotes of underworld life in mid-20th-century Toronto the Good, Davy The Punk depicts a son’s poignant search for his infinitely resourceful, elusive and wounded father. Bob Bossin has penned a witty and generous memorial to a man, we sense, he is still seeking to know.’

—Gabor Maté M.D., author of In The Realm of Hungry Ghosts and Scattered Minds

Unpublished endorsement

Davy the Punk is a terrific read, both a loving biography of a "little guy" and a fascinating social history. A real page-turner.’

—Cyril Levitt, author of The Riot at Christie Pitts

Unpublished endorsement

‘A life so fascinating, hilarious and outrageous, it’s worthy of a Mordecai Richler novel.’

—Andreas Schroeder, author of Robbers and Renovating Heaven


Born in Toronto in 1946, Bob Bossin has spent 40 years writing and performing music and stories, including as the founder of the legendary Canadian folk group, Stringband. Called "funny, informative and inspiring at the same time" by Pete Seeger, Bossin has recorded a dozen albums, performed all over the world and added a number of songs to the Canadian folk canon. His essays and journalism have appeared in many major Canadian newspapers and magazines. He has also written several plays and poems. Concurrent with the release of Davy the Punk, Bossin will be touring a live one-man musical about his father. He lives on Gabriola Island B.C. with his son, Davy, and his partner, visual artist Sima Elizabeth Shefrin.

For more information please visit the Author’s website »

The Porcupine's Quill would like to acknowledge the support of the Ontario Arts Council and the Canada Council for the Arts for our publishing program. The financial support of the Government of Canada through the Canada Book Fund (CBF) is also gratefully acknowledged.

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HISTORY / Canada / General

ISBN-13: 9780889843691

Publication Date: 2014-03-03

Dimensions: 8.75 in x 5.56 in

Pages: 192

Price: $22.95