Racetrack Man

A son tells the story of his father’s checkered career

The last time anyone was certain about the character of Toronto was in the 1940s and the ’50s, when the city was shut up tight on Sundays and the rest of the week was just as prim.

In recent years, Toronto has been in flux. We have traded our staid WASP stance for a glorious, riotous international multiculturalism; if we are emphatically not what we used to be, we do not yet know what we will become.

In the search for answers there are many fine books about Toronto’s past, and even one terrific play—written by former mayor John Sewell about another former mayor Allan Lamport—but I have always wondered if there was an ur-text to explain this confounding town, some fundamental document that shows who we really were, once, here.

After all, other important cities have had their inner lives exposed, and often by newspapermen: the Chicago of Mike Royko, the Philadelphia of Pete Dexter, the Montreal of William Weintraub.

Perhaps the best match of scribe and city is New York and Joseph Mitchell, whose magnificent collection of feature stories, Up in the Old Hotel, and Other Stories, is full of oyster men, sporting men, cranks and eccentrics; it is a living history of the liveliest city on the planet.

We have had no such book about Toronto.

Until now.

Bob Bossin is a musician and singer who fronted Stringband, one of the smartest and the sweetest of the folk groups of the 1970s. More to the point, his father was a Toronto racetrack man known to some as Davy the Punk.

Davy was a quiet fellow who worked, with remarkable efficiency, on the shady side of the street. He was on easy terms with bettors and gamblers, touts and handicappers, guys and dolls. He rubbed elbows with mobsters in this country, and the one to the south of us.

He died when Bob was in his teens.

Who was Davy? And who is Bob? The underpinning of those questions is the basis for this book, and it is a particularly North American quest: sons sometimes wonder who they are as they get older, and they sometimes look to their fathers for answers.

In this case, the elder Bossin was a major-league character in what was then a minor-league city. But because of the nature of his work, Davy left little that is tangible behind, with the exception of some lovely, mostly true stories.

One of my favourites was reported in Davy’s obituary in the Toronto Star, and here I should point out that it is not every denizen of the track who merits a Star obit. It seems Davy once picked the correct win, place and show horses eight times in a row. I do not have a calculator big enough to figure those odds, and you might be forgiven for ­wondering if he somehow knew the results ­beforehand.

There are other, equally delicious stories, told not of Davy but by him, including one about a man who parlayed a $2 bet into winnings of $16,000 and then lost it all; when the man’s wife asked how he had done at the track, he said, “Same as always … I lost two dollars.”

A town that produces men like that is a town you want to know. But what really impels this book is the fact that Davy died when Bob was young.

In order to answer the existential question “who am I?” Bossin not only looks to his father, but also traces his family’s long hard roots in the Jewish diaspora. Some, not all, of this is interesting. But Bossin reminds us of what it was like to be Jewish in Toronto in those old days: the racism was not subtle, and that is important for all of us to know, in light of Toronto’s sometimes not-so-pretty attitudes toward immigrants today.

If the regular world was not accessible to Jews in Toronto, there were always other ways to make a living. Gambling was one of those ways, and Davy the Punk is a lively primer about how to make a safe bet, and about how bookies protect themselves from losses.

Also, for a time, Davy ran a lucrative, if legally dodgy, race wire—whenever the results from a track were telegraphed in Morse code, they were intercepted and decoded, and the results made available instantly, over the phone, to bookies. The service took some of the risk out of the equation for anyone taking bets, and it also came with a tip sheet containing inside information about horses and jockeys and so on—anything that might give a bookie an edge. Here I merely observe that Davy would have been a terror on the internet.

Davy eventually got out of the gambling business. He was one of the few people, it seems to me, who walked away from the Mob without reprisal. More to the point, Bossin’s mother told him that Davy got out so that his son would not be drawn to the life. All this stuff is gold, if you thought Toronto was a dull place.

I do have some minor quibbles: the book is built on memory, and on stories told by others, but Bossin imagines certain conversations as they might have taken place. Often these sound forced, or over-eager. It seems to me that when men tell stories to each other that they have told before, the language tends toward the subtle or the polished, as opposed to the eager—more like prayers than news.

Nor was I always with Bossin on some of his explanatory excursions. I do not really expect him to outline American gangland history.

I also wanted more of his lovely mother, who provides many grace notes in the book.

But that is minor stuff.

When Davy the Punk died, the younger Bossin kept his sorrow to himself, as he had been taught to do. Pay attention now—the concealing of emotions is not just a WASP trait; it is also a trait of gamblers.

And I do not want to give the game away, but when you read this book, then you will be forced to examine the separate worth of patrimony and paternity.

Here is something: when Davy the Punk left the track, he became a booking agent who handled bands.

Bossin, of course, had Stringband: was he seeking some sort of approval, finding a way to be wanted—a way to be booked—by the bookmaker who left his life too soon? Maybe that is just speculative hooey on my part.

Bossin writes, “I have often wished I could trade some of the time I had with Davy as a boy, for time together man to man. There are so many things we never talked about … love, or sex, or marriage.”

They may not have talked about those things but Bob, a word—he taught you better than you knew.

In the end, I think what Bob Bossin got from Davy the Punk was his sense of fearlessness, his sharp eye and his willingness to stand up in front of others without blinking.

Do not read this as a father-and-son memoir; read this book—and you should—if you want to know what Toronto was, once, when there were a lot of smart, tough guys working the phones, fixing the races, and calling the shots.