Features
Remembrance of Rupertsland Avenue – 1950 to 1975
By BRIAN M. GILFIX Cote Saint-Luc, Quebec September 18, 2023 I have read with interest in various past issues of the JP&N (Sept. 16 and 20, 2019, Sept. 30, 2020, and Nov. 10, 2021) descriptions of streets or blocks where all or most of the houses were occupied by Jewish families. (Ed. note: All those stories – about McAdam Avenue and Bredin Drive, can be found on this website. Simply go to “Search archive” and enter the name of either street. The entire issue in which the story about that street appeared will show in the search results.)
This was not all that unique in the 1950s and 60s, especially with the Jewish population of Winnipeg peaking close to 20,000 individuals during that time. During the immediate post-war years, individuals and families were leaving the Magnus and Flora Avenues with their wooden shuls and moving more northward to the then developing West Kildonan and later developing Garden City areas. This was reflected in the establishment of shuls (Rosh Pina, 1952; Bnay Abraham, 1958; Chevra Mishnayes, 1965) and schools (Talmud Torah, 1952) in the area.
Rupertsland Avenue was a new street developed in 1950 by Edward Rosenblatt. The street name obviously echoes the name given to the territory draining into Hudson’s Bay , which was called Rupert’s Land. Looking at the actual mortgage documents, houses cost about $8450 for a bungalow (1 storey) while a cottage (2 storey) cost about $2000 more. By the mid-2010s the value of a bungalow style house had increased thirty-fold in value. The street changed appearance somewhat over the years with some upgrades – paving of the back lane (1950s) and planting trees on the front boulevards (1960s).
I grew up on Rupertsland Avenue in the 1950s and 60s. Then, in the block stretching from McGregor St. to Parr St. and comprising about 50 houses, over a third of the houses were occupied by Jewish families. Most were tradespeople or small business owners. None of that generation were professionals. Then, your neighbours were also your friends with whom you socialized. For example, my parents belonged to a bridge club on the street, comprising amongst others the Stollers, Brasses, Bogaches, and Jacobsons. As few trees were planted, we, the neighbourhood children, played across the front lawns of neighbouring houses, effectively making one long field.
The children (including myself) walked to the local schools regardless of the weather: Victory, what was then known as Jefferson Junior High School, Garden City Collegiate, and Talmud Torah – affecting the school demographics such that on major Jewish holidays the public schools “shut down.”
We had deliveries from the milkman and bread man. The street was visited by vendors selling eggs and, on one occasion early on, vegetables from a horse drawn wagon.
From my memory, I have provided a list of the Jewish families that lived on the street during this period. I have also given a few short vignettes of some families as I remember it from my then youthful perspective aided by information gleaned from the JP&N and Google. I apologize for any errors in advance. I should note that of the families listed here, with rare exception, the parents have passed away. In some instances, I have noted the year of passing.
565 Rupertsland – Stoller. He was an accountant or bookkeeper. He and his wife had a son & daughter, Elaine (?).
517 Rupertsland – Name unknown.
513 Rupertsland – Kesten. Their son Cyril currently resides in Vancouver.
509 Rupertsland – Tennenhouse – Sam (d.2001) and Gertie (d.2014).
They had four children: Karen, Ronnie, Marsha, and Kenny. He farmed with his brothers during the summer and had a small machine shop in the basement in winter where he made house numbers. They were long time friends of my parents. They had a “bogey man” is their basement, actually an old coal style furnace. The oldest daughter would bang on it to make the “monster” noise to frighten the kids. They were perhaps the first family to leave Ruperstland for the then new Garden City. I believe some family members still live in Winnipeg, but the son Ronnie lives in Toronto.
505 Rupertsland – Gilfix (us) – We were Joseph (d.2014), Betty (d.2021), Debbie (Edmonton) and myself (Montreal). My parents moved to a new home on Rupertsland in 1950 from the Carmen Apartments on Burrows, which is still standing, leaving behind a walk up and ice boxes. The years saw a transition for heating the house with coal to oil to gas. My sister left for Edmonton to attend university, later married there, and has lived there since. My journey was more peripatetic, moving in 1975 to London, Ontario to pursue my PhD, followed by a post-doctoral fellowship at Harvard Medical School, and finally returning to Canada and McGill University to pursue my MD degree and specialty training. I married in Montreal and have been on staff at the Royal Victoria Hospital in Montreal since 1993. Due to age and infirmity, my parents finally left Rupertsland in 2014. I believe my parents were the last Jewish family on the block and street when they finally left.
501 Rupertsland – Dutkevich – Ann Dutkevich (d.2000), husband Nick, daughter Sally and son Joe. She was affectionately known to us as “Mrs. D”. She was very kindly. Once, when my sister decided to “run away,” she packed her bags to move to Mrs. D. next door.
I believe the children still live in Winnipeg. Their house was later purchased by another Jewish family, the Greenholtzes (daughter Faye & son Joey). He was a tailor and both he and his wife worked in the garment factories. The parents later relocated to Toronto to be closer to their children.
493 Rupertsland – Gabor. They had a son, Brian.
489 Rupertsland – Name unknown.
485 Rupertsland – Bogach – Frank and Ann, her mother, and son Howard. Frank with his brothers ran Tasty Seeds located on Alfred that they had inherited from their father. Howard was recently profiled in the JP&N (August 16, 2023).
469 Rupertsland – Bogach – Maurice & Goldie Bogach and their daughters, Mindy and Evy. The parents played bridge with my parents and he owned Tasty Seeds with his brothers. I believed their children still reside in Winnipeg.
465 Rupertsland – Rodin. One of their two sons, Greg, is a lawyer in Calgary.
461 Rupertsland – Brass – Abe and Rose Brass and their children. Following his passing she moved to Vancouver to be closer to her children, where she later passed away.
516 Rupertsland – Plosker – Max and Bertha Plosker, daughter, and son Erron. The family owned Direct Home Furniture
512 Rupertslsand – Spiller – Jack and Ailenne and their children, Harley, Susan, Sari, and Deborah. I believe some of the children still reside in Winnipeg.
508 Rupertsland – Terhoch – Kurt & Pearl. He was an electrician. They had two sons, Leonard and Marvin, and a daughter, Cheryl. The oldest son, Marvin, was at one time a producer at CBC Winnipeg.
504 Rupertsland – Jacobson – Anne, Nat (d.2002), son Gary and daughter Arlene. Nat had a part job running the projector in movie theatres. At 106 (!), Ann is probably the last living individual of the generation that first moved onto Rupertsland Avenue. She currently resides at the Simkin Centre. Gary still lives in Winnipeg.
496 Rupertsland – Chodiker. One son, William (Bill), is an allergist, now retired, who lives in London, Ontario.
476 Rupertlsmand – Golubchuk – Samuel (d.2008) and Dora and children, Percy and Miriam. I believe they were the last Jewish family to move on to Rupertsland. Samuel was at the centre of a controversial legal battle dealing with the question of who has the right to make end-of-life decisions. This case was widely written about.
468 Rupertsland – Beloffs
Lastly, at the end of the street, there was a corner store (700 McGregor) run successively by Jewish owners, Mandel and later Slutsky.
Interestingly according to my late mother, Paul Snider of Dorothy Stratton murder fame, apparently lived on Rupertsland Avenue for a period of time.
Rupertsland was not a Jewish island in West Kildonan. Immediately behind my parents’ house across the back lane on Enniskillen Avenue, there were the:
Bokauts with sons, Barrie and Brad. I remember walking back home with Barrie and his father from the Bnay Abraham synagogue on Shabbat mornings. Barrie went on to work for Foreign Affairs Canada. I believe Brad still lives in Winnipeg,
Lezacks whose son, Jack, is a hematologist in Winnipeg, and
Este and Morris Katz. Their sons, David and Philip, tragically past away at early ages.
On Smithfield, there were other Jewish families such as the Senenskys and Gorewiches (my father’s brother-in law and sister).
Over the decades the ethnic and religious composition of Rupertsland Avenue changed as the original inhabitants aged and they and their children moved to other areas. Many of the children left Winnipeg – often to Calgary, Edmonton, or Toronto. Consequently, the demographics and character not only of the street but also of the local schools, institutions, and West Kildonan have changed. On Rupertsland at its peak, probably a third as many Jews lived there alone as compared the number of Jews now living in the entire West Kildonan area (205) according to the latest census. Consequently, many of the local Jewish institutions have moved, closed, or amalgamated. When my parents, being the last Jewish family on that block of Rupertsland Avenue, finally left in 2014, it marked the end of an era for the street.
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
