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Rosie Sharp: wife of Four Seasons Hotels founder Issy Sharp lays it all out in her memoir

book cover edited 1By BERNIE BELLAN I’m not much for reading autobiographies; I prefer to read someone else’s account of a person’s life because I figure you’re much more likely to find out what someone’s life was truly like when it was written by someone else – warts and all.
However, when I was asked whether I might like to receive an advance copy of the memoir of Rosalie Sharp whose name, to be honest, was unfamiliar to me – but who, I was informed, was the wife of Four Seasons Hotel founder Isadore Sharp – I thought: Sure, it’s always interesting to read of the lives of the rich and famous – and when they’re Jewish and Canadian to boot, let’s go for it.

Now, to be even more honest, as much as I’ve heard plenty about Four Seasons hotels – that they set the standard for service and luxury when it comes to hotels, I had never read much about Isadore Sharp. How much would his wife want to talk about her husband in her memoir, I wondered? And how good a writer would she be?
The answer to the first question is: Quite a bit, while the answer to the second question is that Rosalie Sharp is an excellent writer. No doubt she received quite a bit of help in putting together this very interesting book but, as she explains early on, she has written quite a few books previously, mostly having to do with interior design – which is one of her two utmost passions – the other being painting.
What surprised me most about Rosalie Sharp though is how much her formative years as a young girl in Toronto still leave a strong imprint on her, even today, as she must now be 87. (She completed the book in 2021 when she was 86, she explains.) Isadore, by the way, is 91. They’re both as healthy as one could hope two seniors in their dotage could be expected to be. As a matter of fact, “Rosie”, as she prefers to be known, is quite candid in describing her own health situation. At one point she tells a funny story about having a colonoscopy recently, but while she is driving home in Issie’s fancy Mercedes, she can’t hold it in. She goes on to tell how she hid her accident from Issie when she came home, stripping off her dress without him seeing and running out to the car with a pail of soap and water and cleaning up.

The book is full of interesting stories. Rosie (née Wise) grew up in a very poor household in the 1930s – where there was no telephone, but where the phone book served as a substitute for toilet paper. Her parents lived in a non-Jewish area of Toronto, where they ran a dry goods store. Mr. Wise was also an excellent tailor. As for Mrs. Wise, however, Rosie still has an aversion to soup, she explains, after having grown up smelling her mother’s absolutely horrible broth – which she could never bring herself to taste.
Although the book devotes a certain amount of space to describing Issy Sharp’s much more comfortable upbringing – which Rosie writes about in an early chapter, prior to going into detail about her own much more difficult childhood, the lesson that one takes from reading about young Issy is how brimming with confidence he was, even at a very young age. Not only that, he was extremely good looking – as the very many photographs interspersed throughout the book illustrate.
He was also a terrific athlete. Issy was gifted in so many sports, while Rosie never had the opportunity to take piano lessons, which she so desperately wanted to take as a youngster. She also never learned to swim, she admits, but that didn’t stop her from being a sport and donning a life jacket while going on a canoe trip with the family once – or even waterskiing.

The story how Issy and Rosie met at a wedding makes for a great romantic tale. But Rosie admits that she knew of Issy’s reputation as a consummate ladies’ man – and she honestly doubted that he would remain true to her once they became a couple. There are quite a few instances in the book when Rosie describes her own naiveté about sex – something with which Issy was extremely well versed. (He was 22 when they met; she was 17.) Yet, he was always extremely considerate toward Rosie when it came to the physical side of their relationship. She does reveal though that she became pregnant when she was only 19 and did have an abortion because neither she nor Issy were ready to start a family at that point.
While the book does a good job of delving into how Issy Sharp was an absolute genius when it came to building – not just hotels, but apartment blocks as well, to the point where, as of the date of publication of the book, there are now 134 Four Seasons hotels throughout the world, it wasn’t the pursuit of riches that drove Issy, according to Rosie. They have certainly led very comfortable lives, but the first five years of their marriage were spent living in a very humble apartment, she says, and although they’ve moved several times during their lifetime together, it’s been the building and decorating of homes that has been the attraction for them, rather than the accumulation of “toys.”

In fact, Rosie never cared much about things like cars, she says. In one amusing anecdote she describes her driving in what she thought was a Toyota Land Cruiser for years, only to discover that it had a Volvo logo in it. As a collector though, Rosie has been obsessed with the accumulation of ceramic figures, along with a certain number of paintings, she notes – but it’s her ceramic figure collection, which extends into the thousands, of which she’s proudest.
Early on in life Rosie exhibited true artistic talent. She tells of drawing hand lettered signs for her parents’ dry good store that were so well done that people seeing them thought they had been printed by a machine. Later she parlayed her artistic eye into a love for interior design. Even while she was raising four young boys, Issy encouraged her to acquire a formal education in interior design, which she did. She eventually opened her own interior design firm. Much of her work, as one might expect, was for Four Seasons hotels, but she wasn’t given the work simply because she was married to the boss. Issy pays full credit to the many innovations Rosie introduced into the hotels over the years.
At times though, I must admit I was somewhat bored reading Rosie’s quite detailed descriptions of her projects. While she is certainly extremely descriptive, I’m not sure how much readers really care to read about design – whether it be interior design or the design of ceramic objects. Of course, those are both two of Rosie’s passions – and she is allowed to indulge herself as much as she likes. It’s her memoir, after all.
Where I think Jewish readers of a certain age will find this book most resonating though is when Rosie writes about the many relatives she lost in the Holocaust. There is a great amount of time spent exploring the lives of her predecessors in Poland. Rosie can trace her family roots back to the 1700s. (She also does quite a bit of the same for the Sharp family.)

Both she and Issy grew up in Yiddish-speaking households and Rosie harbours a great deal of nostalgia for those early years. Like most Jews growing up in the 1930s the Wise household was an observant home. (She tells a hilarious story about being sent to a butcher a long way off to buy a chicken for the Friday night dinner, but having the bloody chicken, freshly slaughtered, ooze all over her on the bus ride home.) She also emphasizes how important having regular Shabbat dinners with their family has been for both her and Issy throughout their lives – only to see that disrupted when Covid hit. (As a matter of fact, it was Covid that led to her writing this book, as she found that she had quite a bit more time on her hands than would normally have been the course.) In a departure from her observant upbringing though, Rosie says the only time she sets foot in a synagogue nowadays is during Yom Kippur – and that she doesn’t believe in God.
Interestingly, while Rosie acknowledges the role she’s played for years as the wife of a charming and brilliantly successful businessman, accompanying him on many trips to far off lands where it was her duty to sit through endless dinners with some of the world’s most powerful figures (including one ghastly dinner in Japan where she says the fish that was served was still wriggling!), Rosie hardly sees herself as a society maven. She did her duty – and often contributed to the success of Four Seasons on her own, both as a designer and as the gracious wife of a very powerful man, yet she notes over and over again that she feels most at home in her own house – and there have been many different ones over the years, including a home that they rebuilt from scratch in Palm Springs.

Issie Rosie SharpHere’s a description of Issie and Rosie’s harmonious relationship, as given by their son Tony on the occasion of their 62nd wedding anniversary:
“She paints. He promotes. They are full-fledged partners in life.
“Partners in bridge: she is the one who takes the risks and swings for the fences, and he plays more by the book and the percentages, yet rarely an argument, and they regularly place near the top.
“Partners in design…not the least of which is their new bungalow, where our dad concerned himself with light, views, and land assembly, and our mom, the architecture, interior design…Partners in dance. and, can they dance! Partners in fitness – still following Jane Fonda’s Advanced Workout from 1985…
“Partners in philanthropy. Including what our mother considers one of our father’s best achievements: establishing the Terry Fox Run. Proposed in a telegram from our dad to Terry, the run is now the largest single-day fundraising event in the world, having raised $750 million for cancer research.
“And of course, partners as parents. Sharing and living the values that have guided us as a family, and for which we are grateful.”

By this time, if you’ve read this far, you must be thinking: What a perfect couple – and I’m sure they are, but if I could ask two questions of Rosie, they would be this:
You had a son named Chris who died tragically at only age 17 when a melanoma was improperly diagnosed by a doctor. You write so eloquently of what that loss meant to the two of you – as I’m sure it would to any other parents who have lost a child.
But – why “Chris?” I know that it’s not totally unheard of for a Jewish child to be named Chris or Kristina, although from what I’ve read, it’s often when one of the parents isn’t Jewish. But both you and Issy came from traditional Jewish upbringings. Was there a particular reason that you chose to name your youngest son “Chris?”
And, my second question: I had to do some research to see that you and Issy have contributed substantially to many different causes, including the Hebrew University of Jerusalem. But nowhere in your book do I see any evidence that you took a particular interest in philanthropy yourself, especially as it relates to Jewish causes. I would imagine that someone of your renown would have been asked many times to lend their name to a particular Jewish fund-raiser. Perhaps it wasn’t of sufficient interest for you to write about that – or maybe it just wasn’t your thing. But, as someone who espouses the importance of Jewish values so strongly, wouldn’t “tzedakkah” have been one of the most important values? I’m not saying this as a criticism because I see that when you do a search of all the causes to which you and Issy have contributed, the list is a lengthy one. But I’m somewhat puzzled that, other than the Terry Fox Run, there’s no mention of any other cause to which you might have attached yourselves. After all, Issy is worth over $500 million from what I’ve read (while the Four Season hotel chain, which is now owned primarily by Bill Gates – is valued at over $10 billion).
Still, let’ s not let these fairly petty questions detract from what is, on the whole, quite the entertaining read.

“Me & Issy – A Four Seasons Romance”
By Rosalie Wise Sharp
Published by ECW Press, Toronto, 2022
274 pages
Available in both print and Kindle editions

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“Two Weeks in Toronto” is a sweet romantic novel, but with some major shortcomings

book cover/author Amelia Doyle

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

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Today’s “Anti-Zionist” Propaganda was Nurtured in the Soviet Union

cartoon from a 1972 Soviet Union publication

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.

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“Kaplan’s Plot” – newly released novel set in Chicago is both historical fiction and psychological drama

Jason Diamond/cover of "Kaplan's Plot"

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

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