Features
A deep dive into the lives of some shadier members of our community
By BERNIE BELLAN A few weeks ago I was contacted by a publicist for a publishing company, who asked me whether I’d be interested in obtaining a copy of a new book, titled Jukebox Empire: The Mob and the Dark Side of the American Dream?
Here’s what that publicist wrote: “This fall, Rowman & Littlefield is publishing a true crime book focusing on one of the key figures in the story of organized crime in the 20th century – Jukebox Empire: The Mob and the Dark Side of the American Dream by David Rabinovitch (publishing October 15). Rabinovitch, an award-winning filmmaker from Morden, Manitoba, unravels the story of his uncle William “Wolfe” Rabin, which takes him from the Canadian prairies to Chicago in the 1940s and Rabin’s invention of a jukebox. This is the first book to expose how organized crime infiltrated the jukebox industry and it’s an untold piece of criminal, cultural, and musical history. Rabin was the son of Jewish immigrants.

“Caught between the Mob and the feds in a plot to save the casinos in Havana from Castro’s revolution, Wolfe Rabin pulled the biggest money-laundering scheme in history, but his hubris led to the conspiracy falling apart in a sensational trial. At a time when there was a jukebox in every restaurant, diner, bar, barracks, arcade, and canteen, Rabin’s trajectory from inventor to promoter to outlaw is set against the Mob’s growing influence of the jukebox industry. In a world of music, machines, and money, popular culture and organized crime collide in this true story of invention and greed. Rabinovitch pieces together the puzzle that begins in Chicago and spans the casinos of Havana and the financial giants of Europe, leading to what the FBI called “the biggest bank robbery in the world.”
“Rabinovitch is a winner of Emmy, Peabody, and Gemini awards. His significant films include the documentary Politics of Poison and the mini-series Secret Files of the Inquisition. Jukebox Empire is his first book.”
Of course, the moment I read that email I was interested in reading the book. Here we have some of the essential elements of a story that’s perfect for this paper: A crime story with a Jewish character at its centre – who comes from Morden, Manitoba no less!
I immediately thought of historian Allan Levine, who’s written extensively about Jewish characters with sordid backgrounds – especially in the bootlegging business, and contacted Allan to ask him whether he’d ever heard of this “Wolfe Rabin?”
Allan said he hadn’t previously, not that is, until he was contacted by the author, David Rabinovitch, who asked Allan for some help.
After I began to read the book, however, I was again contacted by the publicist, who asked me to withhold writing a review of the book until October, when the book will be released to the public.
But, to whet readers’ appetites even further, here are some endorsements David Rabinovitch has already received in advance of the book’s actual release to the public:
“A fast-paced, colorful romp through a slice of the twentieth century American underworld”
-David Kertzer, Pulitzer Prize winner
“Jukebox Empire reads like a novel but the characters and events are real and chilling.”
-Peter Edwards, co-author, The Encyclopedia of Canadian Organized Crime
“It has everything: action, incredible characters, suspense, humor. Can’t wait to see the movie.”
-Fred Fuchs, producer, The Godfather, Part III
“A compelling story of family and crime that touches on key events of U.S. history in the 1950s and 60s”
-Scott M. Deitche, author, Garden State Gangland
“An eye-opening, informative, and fascinating book. Jukebox Empire is must-read.”
-Antonio Nicaso, author, Made Men, The Dark Mafia, Angels Mobsters & Narco-Terrorists
“A delightfully entertaining story of jukeboxes, money laundering, and stolen bonds.”
-Alex Hortis, author, The Mob and the City
“A unique combination of family memoir and investigative journalism.”
-Gary Jenkins, producer/host, “Gangland Wire”
“A tour-de-force account of the Mob’s growing infiltration into legitimate American industry and how it affected one man who was obsessed with power and money at all costs.”
-Joe Saltzman, Prof. of Journalism, Annenberg School of Communication, University of Southern California
I also asked David Rabinovitch whether readers could order Jukebox Empire in advance, so that they could obtain a copy as soon as it’s released.
David responded: The book “is available for pre-order online through the website www.jukeboxempire.com (Chapters Indigo in Canada) or readers should request it at their favourite bookstore.”

All this got me to thinking: Over the years, we’ve published quite a few stories about Jews with mob connections, and some of those individuals came from Winnipeg. Perhaps the story that elicited the most interest was one we published in 2015 by Martin Zeilig about a character by the name of Al Smiley. (You can still find that story on our website’s online archive. Just search for “Al Smiley.” in the “search archive” button on jewishpostandnews.ca)
Smiley, it turns out, was best friends with Bugsy Siegel (whose real name was Benjamin – and who hated being called “Bugsy.”) In fact, Smiley was sitting right beside Siegel – on his living room couch in his Las Vegas home, when Siegel was shot and killed by a Mafia hitman.
That story led to another story about a mobster with a Winnipeg connection who, it turns out, was actually related to me in a very distant way, someone by the name of Harry Altman.
In 2020 I wrote about someone by the name of John Novick in an article I wrote about the children of Jewish mobsters. In that same article I referenced Myer Lansky and his daughter, Sylvia, who was the subject of one of the greatest interviews Anna Maria Tremonti ever conducted when she was host of CBC’s “The Current.” (You can still listen to that interview on the CBC website.)
Finally, a few years back I happened to attend a Fringe show which was titled “Davey the Punk.” The creator of that show – and its sole performer, was singer Bob Bossin (who was a member of a well-known group called “String Band.”) The show was about Bob’s father, Davey Bossin who, while not a “made man” per se (Mafia parlance for someone who is accepted into the Mafia), but who was very “connected” and about whose background Bob Bossin knew nothing until years after his father had died.
What’s my obsession with mobsters, you might ask? Well, I don’t think I’m much different than a great many others when I say that I’m both fascinated and repelled by all these figures – and the fact they’re all Jewish only adds to my interest.
But, it got me to thinking – once again: Where are the stories about Winnipeg Jewish hoodlums from the North End? Even in Russ Gourluck’s masterful history of Winnipeg’s North End, The Mosaic Village, he only mentions two shady characters: Stanley Zedd, a well-known operator of gambling establishments, especially the Margaret Rose Tea Room on Osborne, and Bll Wolchuk, a major bootlegger in the 1920s.

So – to find out more about Jewish hoodlums of a bygone era, I turned to my most trusted source on the subject: Ernie Chisick, whom I first met at the Y reunion in 2019.
For those who don’t know Ernie – he is a raconteur of the first order and his own brushes with the law when he was younger only add to his mystique.
I sat down with Ernie one recent evening and asked him to repeat some of the fabulous stories he’s told me over the years about colourful North End characters with whom he crossed paths over the years. I was especially keen on hearing Ernie recite some of the nicknames of guys with whom he associated when he was younger.
The problem is, as Ernie explained, some of those individuals are still alive and, even if they’re not, they have kids and grandkids, so referring to them by their full names might not even be embarrassing, it might be potentially lethal for me!
I have attempted to reach out to one character in particular who, as Ernie described him, probably knows more about Jewish hoodlums… and criminals, from the North End of the 40s and 50s than anyone else alive, but even if that guy does get back to me, I rather doubt he’s going to want to see his name end up in the Jewish paper in Winnipeg. (I’m hoping that he will respond to my message and I’ll promise him full anonymity if he’s prepared to talk about his former friends – who weren’t quite boy scouts.)
Ernie though, has too many good stories not to at least refer to some of them here. He told me about a gambling club on Selkirk Avenue between Salter and Powers that was run by an individual who was known as “Montreal…..” (Again, I’m leaving out the surname because it’s a name that would be familiar to at least some readers.)
According to Ernie, that club had a lookout by the name of “Srulik Flaxman.” When Srulik would spot a cop coming, he would shout to the guys who were in the back room: “Watch out – it’s the football shoes kimmen!” (Why he referred to cops as “football shoes,” Ernie didn’t know.)
Here’s another story Ernie tells – about a character who went by the name “One-eyed Connolly.”
“They’re playing cards,” Ernie says, “and Connolly says he’s got to take a piss.” But before he gets up to go to the bathroom, he leaves his cards on the table, then takes out his glass eye, puts it on the table, and says to the eye: “Watch them guys; they’re all a bunch of thieves!” Apparently that so unnerved the other players, they sat there frozen in their seats, afraid of that well-known Jewish superstition: “the evil eye.” (But Connolly wasn’t Jewish. Can a non-Jew threaten someone Jewish with the “evil eye?” There’s a Saturday morning sermon for you, all you rabbis and would-be rabbis out there.)
With reference to Stanley Zedd and the Margaret Rose Tea Room, Ernie says that his father, Charlie, once said to him, “Take this to the Rosie (the nickname for the Osborne Tea Room) and ask for Stanley Zedd.” Charlie handed Ernie a paper bag (which, Ernie now says, unbeknownst to him at the time, contained betting slips. Ernie claims he was only an innocent 16-year-old. not yet wise in the ways of the world. Anyway, the statute of limitations protects him now.)
So, Ernie drove to the Tea Room and announced, when he walked into the room, “I have something for Stanley from Charlie.”
He was ushered into the back room where Stanley Zedd held court. “He was very nice to me and told me my father was an honourable man,” Ernie recalls.
Another time, Ernie says, he got a phone call from his father in the middle of the night.
“Charlie,” Ernie asked (Ernie says he always called his father by his first name), “what is it?”
“I’m in jail,” Charlie responded. (He didn’t say why.)
“In the morning,” Charlie continued, “give Roland Penner a phone call.” (Roland Penner would go on to become Manitoba’s attorney general, but at the time he was in partnership with Joe Zuken in the firm, Zuken and Penner.)
“So, I phoned Roland Penner’s office in the morning. I told his secretary who I was and she put me through immediately to Roland Penner.”
“Roland says to me, ‘You heard from your dad? The mounties made a raid in the middle of the night. Eighteen guys (from different cities) were charged with conspiracy to commit bookmaking.’”
“Roland says: ‘I’ve got something for you.’ “ He explained that the mounties took Charlie out in the middle of the night and it was quite cold.
“Your father wanted me to give you his gloves,” Penner continues.
“I put them on,” Ernie says, “and I feel a lump in one of the gloves. They were betting slips that could have been used as evidence in court.’
(Did Penner know that, I wonder? Ernie says he doesn’t know.)
“All the guys were taken to a lock-up in Calgary. Harry Walsh represented the three Winnipeggers,” Ernie continues.
“My dad explained that the Jewish boys were able to get kosher food to eat because one of the mounties was Jewish and he brought them deli.”
The Grey Cup was being held that week, Ernie says. “Charlie said he made $10,000 taking bets on the game” – while he was in jail.
Eventually, when the accused were brought to trial, they were all acquitted, Ernie explains.
“Walsh said they weren’t betting with each other; they weren’t in business together.” As a result, the conspiracy charge didn’t hold up, Ernie says. (If they had simply been charged with bookmaking, then the likelihood is that at least some of them, including Charlie, would have been found guilty.)
I don’t necessarily approve of Charlie’s behaviour. Rather, the stories about the less savoury aspects of Jewish lives don’t usually receive much attention in North American Jewish newspapers. (Some Israeli newspapers, in contrast, are not at all reluctant to publish extensive investigative pieces about the Israeli underword.)Yet, there are so many colourful stories to tell I thought I’d deviate from the Gerry Posner and Myron Love types of stories that extol the virtues of individuals who have led honest, hardworking lives to write about other less honourable fellows who, as the late Harvey Rosen used to say are “of the Hebraic persuasion.”
We’ll have more about members of our community who had connections to activities that were not always on the right side of the law in our Aug. 16 issue. If you might have a story to add about a relative with a shady past that you might like to share, you can email us at jewishp@mymts.net
Features
“Two Weeks in Toronto” is a sweet romantic novel, but with some major shortcomings
Review by BERNIE BELLAN As the former publisher of The Jewish Post & News, but still publisher of a popular website – jewishpostandnews.ca, I’ve long been inundated with requests to review books.
I tend to ignore almost all those requests – simply because I don’t have other reviewers available who are willing to review books – unlike years past when there were a few different individuals who would be willing to review books for the paper, so it falls on me to do all the reviewing.
Something else that’s happened more and more often in recent years is that authors become their own publicists and can be quite good at drawing attention to their books.
So it was that when I was contacted a month ago by a writer by the name of Amelia Doyle, who asked me whether I’d be interested in reading a book she’d written titled “Two Weeks in Toronto,” the name of that book was familiar to me as Amelia had contacted me last year to ask me whether I’d like to review her book back then.
I did take her up on her offer at that time – and began to read “Two Weeks in Toronto” but, if truth, be told, I lost interest in it. The book had some major flaws – and as romantic fiction I thought it lacked any real spark.
But, when Amelia contacted me again, this time her email noted that the book was a finalist in something called the Canadian Book Club Awards.
Really? I thought. Maybe I was too quick to put that book down – or to turn off my Kindle – as the case may be.
So, I began to read “Two Weeks in Toronto” all over again – with a promise to myself to finish it this time.
I should also add that of the many emails I’ve been receiving in recent years, many have been either from publicists for books or from the authors themselves, and many of the books I’ve been asked to review have been self-published.
It’s not all that difficult to publish a book nowadays and, in fact, many self-published books that I have read have been quite good.
In the case of “Two Weeks in Toronto,” after opening the book again many months after I had first taken a look at it though, I saw that it was published by something called “BRINKLEY Verlag.” I did some research on BRINKLEY Verlag and saw that it’s an Austrian publishing house, but with no information on its website whether it simply publishes books for a fee or whether it actually accepts manuscripts and publishes them without charging the author.
Also, on the title page of “Two Weeks in Toronto,” it says that the book was edited by someone by the name of Kelly McErlean.
Okay – the book had been published by some sort of publishing house and apparently, it had also been edited. I regarded both those things as pluses.
One more thing: I did do some research on Amelia Doyle and saw that she has authored at least a couple of other books: “A Dublin Love Story” and “The Rabbi’s Wife,” so she must have had at least some practice writing novels, I thought. By the way, if you Google Amelia Doyle and see what books she’s written, you can see they’re all described as “sweet romance.”
What does this have to do with my reviewing the book? you must be wondering.
Well, I’ve been in correspondence with Amelia Doyle and she seems such a nice person that I told myself I have to find something good to say about “Two Weeks in Toronto.”
But honestly, I tend to look at the novels my wife likes to read for guidance as to what women like when it comes to romance and many of the titles I see have a mystery element to them – or some rip roaring sex!
Here’s what AI says when you ask it what kind of romance novels women like to read: “Most women enjoy diverse romance novels, from steamy contemporary/spicy reads and funny rom-coms (like Emily Henry) to emotional historical sagas (like Outlander) or ‘romantasy,’ but popular choices often feature strong emotional connection, relatable characters, satisfying happily ever afters’ (HEA), and tropes like enemies-to-lovers or billionaire romance, with recent trends favoring diverse voices and escapism.”
So where does “Two Weeks in Toronto” fit into any of those descriptions, if any?
Well, it does have a romance at the centre of it, but the romance is so predictable that it hardly whets the appetite.
What it does have though, and which might make it of particular interest to Jewish readers, is a female Jewish protagonist by the name of Ciara Walsh. (Ciara, I had to look up, is an Irish name, and is pronounced Kee-ara. What a nice name!)
The person with whom you just know from the outset Ciara is going to fall in love is her dreamy Irish dentist, Ethan O’Leary, tall and blue-eyed – and strange as it may seem: unattached.
At a certain point we find out that Ciara is Jewish – when Ethan comments on the mezuzah on her door, but as to how Jewish she is – well, that was something I began to wonder about as the book went on.
Now, it’s important to note that the book is set right around Christmas – and Chanukah, and the juxtaposition of those two holidays enters into the plot time and time again. There seemed to be so little distinction between the atmosphere pervading both holidays – wintertime, gift giving, family get-togethers, that I wondered whether Amelia Doyle might not be Jewish, but was trying to attract a Jewish audience by injecting some Jewish notes into her book – so I asked her this question: “Are you Jewish in any way, e.g., have some Jewish family?”
Amelia answered: I’m halachically Jewish. “Both my parents come from observant Jewish families and I grew up in a Conservative home.
“Generally speaking, you can find anything from ultra-orthodox to atheist Jews in my family. As you can imagine, living in Europe is not easy as a Jewish person. (I should note that, after further researching Amelia, I discovered that she lives in Dublin.)
“The characters in ‘Two Weeks in Toronto’ were written on purpose in a matter that is more on the liberal side as many of my friends are Reform or in interfaith marriages. This is where the inspiration for this specific book came from.”
In the same email in which I asked Amelia whether she was indeed Jewish, I also noted that I thought the way she intermingled Christmas and Chanukah was deliberately intended to “resonate” with non-Jewish readers.
Amelia responded: “I’m Jewish and there are many ways of practicing Judaism. In this book I decided to write about a non-orthodox Jewish family.”
A “non-orthodox Jewish family?” There’s not much Jewish about them, other than the fact that Ciara’s father, Ian, decided to convert to Judaism when he was younger – for reasons that are totally unexplained. Ciara’s mother, Giuliana (which, apparently, is the Italian spelling for Juliana), is definitely not Jewish, although she doesn’t seem to have much religious orientation either way.
But, let’s not get lost in what is, in essence, a discussion totally irrelevant to this book.
My qualms with “Two Weeks in Toronto” have to do with the writing style – which could have used some good editing. I mentioned that in an email to the author when I was just getting into the book. I suggested that the dialogue could have been much improved had the characters used contractions when speaking, so that for instance, instead of a character saying “I am just stepping out” they could have said, “I’m just stepping out” – which sounds so much more authentic.
Another aspect of this book that drove me crazy is there no explanation for the behaviour of Ciara’s mother, Giuliana, or her sister, Gabriella. Cinderella’s stepmother comes across as kindly compared to Giuliana and, as for Gabriella, who is occasionally referred to as “Bridezilla” by others, well – to use the Cinderella comparison again, she is beyond detestable.
But why? What on earth could sweet, loving Ciara ever have done to provoke such unbridled hatred from her mother and sister? I kept waiting to read an answer – you know, like Ciara was so beautiful that her sister despised her or Giuliana was her stepmother – but no, it’s never explained.
And then there’s Ciara’s relationship with Ethan. Yes, it’s cute how they end up going to Toronto together – to attend Gabriella’s wedding, and they end up sleeping in the same bed together – but without having sex!
So, again, I had to ask Amelia why that was? Here’s what she answered: “In my opinion, most romance books these days are far too explicit. ‘Sweet Romances’ (also known as ‘Clean Romance’) are on the rise again at the moment and this is what my publisher asked me to write.
“Personally, I prefer to have the focus on the relationship and not any sexual relations.
“Not sure about how it is in Canada, but many publishers in Europe as well as the US started publishing ‘clean’ versions of steamier books, not to alienate readers who don’t want to read sexually explicit scenes.”
I’m shattered! “Clean romances” are “on the rise again?” (There’s almost a phallic pun in there, but we won’t go there.)
But hey, it’s almost Chanukah – and Christmas. “Two Weeks in Toronto” is set right around this time of year, so maybe this review is timely. As it’s referred to in the book, this is a book that might make a good read for “Chrismuakkah.”
“Two Weeks in Toronto”
By Amelia Doyle
Published by BRINKLY Vertag, 2024
179 pages
Available on Amazon
Features
Today’s “Anti-Zionist” Propaganda was Nurtured in the Soviet Union
By HENRY SREBRNIK For centuries, Jews have been portrayed, by both religious and secular movements, as obstacles to universal order. Christian theology turned Judaism into the emblem of stubborn particularity. Modern ideologies secularized the script, making Jews stand for capitalism, communism, cosmopolitanism, or cultural decay. In the twentieth century, this logic reached its most lethal form in the fantasy of human renewal through the erasure of Jews, culminating in the Holocaust.
The twenty-first-century iteration recycles the same template in overlapping ways. Islamist movements merge “Jew,” “Zionist,” and “Israeli” into a demonic category whose elimination is a sacred duty. Parts of the Western left have reduced Israel to the very symbol of colonial domination.
What North American Jews are experiencing today, as the ideology of anti-Zionism spreads in left-of-centre spaces, looks eerily familiar to anyone who came of age in the 1970s Soviet Union. Just like antisemites battle against a fantasy of “the Jews” that exists in their own heads, the new anti-Zionists battle a “Zionism” that is conjured up by their own fevered imaginations.
Following the June 1967 war, with Israel’s victory over its Arab neighbours, who were intent on destroying the small Jewish state, anti-Zionism became a central tenet of Soviet propaganda, where “Zionism” was usually equated with self-conscious expressions of Jewishness. It was then that the antisemitic notion of Israel as an heir to Nazism and Fascism was popularized in the Soviet media.
It depicted Israel as the outpost of colonial oppression, Jews as betrayers of socialist internationalism. Soviet propagandists distorted the history of Zionism to underscore its supposedly inherent evil nature, ripping its founders and theorists out of historical context and, absurdly, presenting Zionists as the Jewish people’s greatest enemy. These “rootless cosmopolitans” were accused of corrupting socialism from within. By redefining Jews as racists, Zionism as colonialism, the Soviets handed progressives a vocabulary of virtue through which to disguise an old hatred.
In political cartoons and Soviet propaganda art, swastikas were routinely intertwined with Stars of David, and the Israeli military portrayed as resembling Nazi — and specifically SS — troops. If there is a Soviet propaganda subtext that highlights its ideological and propagandistic roots, it would be “Fascism Under a Blue Star,” the 1971 book by Evgeny Evseev, who had served as an Arabic interpreter for both Soviet leaders Nikita Khrushchev and Leonid Brezhnev. By the late 1970s, he had became one of the principal brains of the ultranationalist antisemitic movement in the USSR, know as the “Russian Party.”
Evseev’s book carried a subtitle redolent of Marxist clichés: “Truth about contemporary Zionism: Its ideology, practice, and the organizational system of major Jewish bourgeoisie.” On the illustration printed next to the title page, there was a black spider with both a swastika and a Star of David on top of its body; the spider’s web was spread over the West, from the United States to Britain, France and Italy.
Perhaps the vilest of all these tracts was “Caution: Zionism! Essays on the Ideology, Organisation and Practice of Zionism,” a 1970 attack by Yuri Ivanov. (By the way, it was republished by a left-wing group, The November 8th Publishing House, in Toronto in 2024.) The book’s singular achievement was to fit classic antisemitic conspiracy theory into the only philosophical framework permitted in the USSR — the Marxist-Leninist one — and rewrite it as anti-Zionist critique.
“Ivanov managed to supply a strong theoretical foundation for openly criticizing Zionism with the help of Marx’s and Lenin’s works, which no one could argue against,” Vladimir Bolshakov, another prominent “Zionologist,” recalled in his memoirs. I remember coming across it in the late 1970s while writing my PhD dissertation on Jews and Communists, and was shocked by its vituperative language and tone, not to mention falsehoods, worthy of the worst Nazi propaganda.
All of this bore terrible political fruit. On November 10, 1975, the United Nations passed General Assembly Resolution 3379, equating Zionism with racism. It remains the foundation stone of antisemitic anti-Zionism. It cast Israel, the collective Jew, as committing today’s ultimate crime. Despite being mass-murdered by Nazi racists, Jews became racists. And despite enduring history’s largest genocide, Jews are now accused of “genocide.”
Communist propagandists enjoyed manipulating words to trigger “Pavlovian” responses, the Princeton Kremlinologist Robert Tucker observed; their “ultimate weapon of political control would be the dictionary.”
Much has been written of late about the deep Soviet roots of today’s virulent anti-Zionism in the West. Some thirty-five years after the fall of the Soviet empire, the Soviet corpse continues to emit its infectious gases and poisons people’s minds and imaginations. After 7 October, parts of the Western Left responded not with horror but with slogans lifted from Soviet propaganda: Israel as colonial, Zionism as apartheid, Jews as global oppressors.
Today’s anti-Zionism is not actually concerned with the relationship Jews have with Israel. It is a project centered on producing villains. In this, it follows its predecessors: antisemitism and anti-Judaism. Antisemites were never concerned with the authenticity of Jewish identity, practice, or behaviour; they sought to construct “the Jew” as a monster.
Anti-Zionism repeats this mechanism, simply substituting “the Zionist” for “the Jew,” while inheriting the same foundational hatred. Failing to recognize that anti-Zionism, whose Soviet and Nazi genealogy reveals that it has nothing to do with Jews and their right to self-determination, is fundamentally a project of constructing fiends.
Antisemitism functions not merely as a prejudice but as a moral language, a grammar that shapes how societies explain disorder and assign blame. It provides simplicity where reality is complex and coherence where the world feels incoherent. For such people, it becomes a battle against a uniquely devious and implacable foe – something that cannot be resolved by elections or arguments, but only by confrontation. The logic points beyond persuasion to elimination.
The only way to be anti-Zionist without being an antisemite is to reject the legitimacy of all nation-states equally. The loudest supporters of Palestinian statehood are not doing that. No one should mistake it, or be taken in by those espousing it, for what it is. We should call it, along with antisemitism and anti-Judaism, as “Jew-hatred.” It is nothing more – or less.
Henry Srebrnik is a professor of political science at the University of Prince Edward Island.
Features
“Kaplan’s Plot” – newly released novel set in Chicago is both historical fiction and psychological drama
Reviewed by BERNIE BELLAN I had been searching for a new book this summer that would be of particular interest to Jewish Post readers when I came across the title of a new book that had yet to be released, called “Kaplan’s Plot.” It had received quite a bit of buzz on a number of websites that spotlight books that have – at least in part – a Jewish theme, although it still had not been reviewed when I first read about it.
The plot of the book, as it was described in those initial previews, certainly appealed to me, as it was said to combine a story about a Jewish gangster in Chicago in the early part of the 20th century with a modern day story about a man whose life had come completely unravelled and who was forced to return to Chicago to live with his dying mother.
I’ve been a fan of Jewish gangster stories for years, especially ones written by our own Allan Levine – and I’d often published stories about real life Jewish gangsters – or Jewish gangster fighters – as the case may be, in the pages of The Jewish Post & News (also on jewishpostandnews.ca).
Last year, for instance, I wrote a review of a book called “The Incorruptibles,” about efforts by law-abiding Jews in New York City in the early part of the 20th century to fight corruption. You can read my review here: “The Incorruptibles.”
Also, in the past I’ve run stories about Jewish underworld figures who either lived in Winnipeg or had a strong Winnipeg connection. One of the most popular stories ever to appear on our website, for instance (and which is still being widely viewed), is one that was written by Bill Redekopp – a former writer for the Free Press, who had profiled a fascinating Winnipeg bootlegger by the name of Bill Wolchock in his book, “Crimes of the Century – Manitoba’s Most Notorious True Crimes.” You can read Redekopp’s story about Wolchock at “Bill Wolchock.”
Another story that garnered quite a bit of attention when it was first published was Martin Zeilig’s story about Winnipeg-born Al Smiley, which appeared in the March 29, 2017 issue of The Jewish Post & News. The most interesting tidibt in Martin’s story was that Smiley was was sitting beside the notorious Benjamin “Bugsy” Siegel when Siegel was murdered in 1947. That story doesn’t appear as a stand-alone story on our website, but you can find it by downloading the entire March 29, 2017 issue by entering a search through our “Search archive” link for Al Smiley.
One more story that dealt with Manitoba Jewish gangsters (and which also referenced the Bill Wolchock story) was one I wrote in 2023 titled “A deep dive into the lives of some shadier members of our community.” In that story I wrote about a book that was about to be published titled “Jukebox Empire: The Mob and the Dark Side of the American Dream.” It was the story of Wolf Rabin (born William “Wolfe” Rabinovitch), written by his nephew, David Rabinovitch.
All this serves as a very long winded preamble to a review of “Kaplan’s Plot.” I was somewhat disappointed to learn that the characters in the book are all fictitious, since the mobsters are so vividly drawn – although there are very brief references to real-life mobsters, including Al Capone, Meyer Lansky and Charles “Lucky” Luciano, that make you wonder whether some of the other mobsters might also have been real people.
According to information available about the author, Jason Diamond, this is his very first novel – a very impressive debut. He certainly brings to life a very nasty Chicago in the early part of the 20th century.
What makes what Diamond has written an even more admirable achievement is that the plot works both as a riveting mystery and as a thoughtful examination of a mother and son relationship.
The story alternates between a story set in modern day Chicago (in 2023) and another story that begins in Odesa in Ukraine in 1909, but soon moves to Chicago shortly thereafter.
At first, we read about a character by the name of Elijah Mendes, who has just returned to Chicago from the Bay area, where a business venture in which he was involved has collapsed. Elijah’s mother, Eve, is dying from cancer, but she certainly retains enough strength to carry on with quite a few activities – enabled by her constant puffing on a vape pen. Eve, it turns out, has been a very accomplished poetess during her life and, although she and her late husband Peter were financially quite comfortable, she scoffs at what she regards as Elijah’s obsession with material pursuits.
Eve doesn’t pay much attention to mundane day to day matters, including opening the mail, but when Elijah discovers a series of letters from something called the Hebrew Benevolent Society, his curiosity is piqued and he sets out do discover what those letters are all about.
The chapters alternate between modern and older Chicago, as we are introduced to the Kaplan brothers – Yitzhak and Solomon or, as they come to be known in America – Itz and Sol. The brothers have narrowly escaped a pogrom in Odesa when their parents were able to secure passage for them on a boat destined for Hamburg. Eventually they find themselves on a ship sailing to America, where they make the acquaintance of a character by the name of Hershey.
Hershey tells the boys that he can help them find a place to live in Chicago, where he introduces them to Avi who, it turns out, is a major figure in the Jewish underworld there.
Diamond provides a rich description of what life was like in Chicago back in the day when the city was divided among different ethnic groups who held sway over their own respective territories and when it was dangerous to cross over into the wrong part of town.
As the story develops, we learn that Elijah is actually the grandson of Itz Kaplan, but knows nothing about his grandfather’s very shady past – beyond having been told that he was a “businessman.” When he goes to the building housing the Hebrew Benevolent Society, however, he finds out that there is an entirely new aspect to his family’s past – which leads to his wanting to probe deeply into his family’s history.
Elijah’s own demons – including past drug addiction, a failed marriage, and a deep insecurity about his own ability to succeed in business, come to the fore, but his mother’s refusal to discuss her family’s history haunts him even further.
As the book moves in parallel tracks between two time periods we find out more about Itz Kaplan – and just how malevolent a character he was. And, at the same time as Elijah learns more about Itz, he begins to better understand why his relationship with his mother had gone off the rails.
The mystery of what happened to Itz’s brother, Sol, about whom Elijah had not even known had existed, figures into both stories – the one set in early 20th century Chicago, and the one set in modern Chicago, as Elijah tries to get his mother to open up about her family.
Jason Diamond provides wonderful descriptions of some of the minutiae of Jewish life back in the day when keeping kosher was an essential element of Jewish life. Sol, for instance, is a butcher (something that his father was as well back in Odesa) and maintains a rigid observance of all Jewish laws. He is fastidious about adhering to the quite complex details of butchering meat according to the laws of kashrut, for instance.
Itz, in contrast, who has been deeply emotionally scarred by what he saw happen during the pogrom in Odesa, is totally indifferent to Jewish laws. At the same time though, the reader might develop a grudging admiration for just how cleverly Itz is able to navigate the jungle of the Chicago underworld. That’s why I began this review by referring to other Jewish crime figures – all of whom existed. While we might be repelled by their behaviour, we are often fascinated by the cleverness they exhibited in maneuvering through the almost constant danger that manifested their lives. And – it was knowing that they were living on a knife’s edge that often seemed to motivate them as they stared danger in the face.
Ultimately, Diamond brings it all home. The mystery behind Eve’s family is solved and there is some closure to the relationship between Elijah and Eve.
A truly absorbing story – although just released in September, “Kaplan’s Plot” has already garnered many positive reviews. One review on Goodreads, I note however, says that the reviewer is sick of “mob stories.” I suppose it’s quite evident that I’m a big fan of mob stories that have a Jewish element and, if you are a fan of that genre then “Kaplan’s Plot” is sure to capture your fancy. I’m not sure I’d recommend it as a Chanukah gift for the grandchildren, however – unless one of your grandchildren has aspirations of becoming a mobster.
“Kaplan’s Plot”
by Jason Diamond
Flatiron Books
320 pages
Published September, 2025
