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
Features
Fake IDs and Underage Bettors: The Growing Problem for Sportsbooks
The expansion of legalized sports betting worldwide has resulted in sportsbooks grappling with a problem that they can no longer overlook: the increase in underage individuals using counterfeit identification to place bets. As more and more ways to bet through mobile apps and online sign-ups emerge, minors who are set on their goal are inventing ways to get around age limits. The emergence of this trend is a breach of the law and morality; however, it is also an enormous problem that threatens the very existence of the platforms, which are forced to rigorously obey the regulations .
Why Fake IDs Are Becoming More Sophisticated
Conventional fakes used to be quite simple to recognize—low-quality printing, different fonts for the text, and inconsistent holograms would make them not very reliable for any kind of verification. But counterfeit documents have changed significantly over time. Nowadays, fakes are made better with the help of printing technology and software, and they can even copy barcodes and other scannable features, so their IDs look almost real.
This fact complicates things significantly for sportsbooks, especially those operating online. Most of the time, automated identity verification systems capture a user’s photo and perform basic data matching. In cases where a very good fake ID is used by a teenager who looks older, some systems cannot recognize the trick. Therefore, young bettors have found ways to be able to place wagers through these loopholes.
The Influence of Social Pressure and Online Culture
Social media is a major factor in the increase in risky behavior that minors are engaging in. On various platforms such as Instagram, TikTok, and Reddit, teenagers come across betting slips, parlay wins, and big-payout screenshots that are shared, most probably, by other users. The glamorization of sports betting is leading young people to copy the behavior of influencers, older friends, or even celebrities, as they think that it is the right thing to do.
The competitiveness usually associated with sports is one of the reasons some minors decide to bet on sports. For many, betting becomes another way to engage as a fan—by predicting outcomes, challenging friends, and experiencing the same excitement that adult fans enjoy. Unfortunately, only a small number of minors fully understand the financial risks involved, making them more vulnerable to developing harmful patterns that could continue into adulthood. This is why choosing the most responsible sportsbook, which you can discover more here, is essential. Such platforms provide guidance, enforce safe practices, and ensure regulated play, allowing fans to engage with sports betting in a more informed, secure, and controlled manner.
Sportsbooks Facing Regulatory Pressure
The sportsbooks are being given the task of more closely monitoring and preventing minors from betting on their platforms. If they fail, harsh penalties are possible, including severe fines, loss of a gambling license, and negative publicity that undermines a brand’s trustworthiness. As a result, it is becoming increasingly difficult for people to verify their identities, although this also inconveniences those who are, in fact, legitimate users.
Sportsbooks have to decide between two options that are in conflict with each other: on the one hand, they have to keep the registration process as simple as possible, and on the other hand, they have to carry out age verification in a very thorough manner. The work of balancing is tough, and the underage gamblers are trying all methods to find a way out.
The Rise of Identity Fraud Services
An alarming trend is the emergence of online vendors who openly advertise fake IDs and identity documents. These vendors often claim their products can pass standard sportsbook checks. Some even tailor IDs to specific regions, knowing that certain provinces, states, or countries use verification systems that rely heavily on image comparison rather than live validation.
The availability of these fraudulent services not only empowers minors but also exposes sportsbooks to risks related to stolen identities, money laundering flags, and fraudulent accounts that may later become legal liabilities.
The Consequences for Underage Bettors
While a minor might think that gambling is just a bit of fun without any harm, the outcome can be quite serious. If there is a catching, accounts are closed right away, winnings are confiscated, and parents or guardians, in some cases, are made legally liable for any financial disagreements. Besides that, the risk of developing a gambling problem in the future increases with early exposure to gambling, especially since teenagers are more impulsive and less capable of handling financial risks.
The majority of minors are not aware that sportsbooks keep very detailed records of their activities, including device information and IP addresses. In case a fake ID works one time, using it multiple times will definitely lead to getting caught.
A Growing Problem That Requires Joint Action
Fake IDs and underage betting are issues that have become a major challenge in the industry, and no single stakeholder can solve these problems on their own. Sportsbooks need to enhance their identity verifications, regulators should get prepared for new types of fraud, technology providers have to come up with new solutions more quickly, and parents should always be aware of what their children are doing online. The industry’s rapid development is making this problem more and more urgent because the number of minors trying to get around the safety measures is increasing.
Sports betting can serve as a fun and legal form of entertainment for adults, but the need to protect the youth is what defines the industry and ensures its survival in the long run. As the quality of fake IDs keeps improving and the online culture is more and more inclined to consider betting as a normal activity, sportsbooks must ensure that underage users do not have access and that the environment is safe for all users. They need to do this now more than ever.
Features
How Canadians Are Adapting to the Boom in Legal Sports Betting
Canada’s fan engagement with sports has been radically changed by the recent single-event legalized sports betting. In the past, this was something you could only do through offshore sites or informal pools, but now it has become a normal part of the Canadian sports culture, according to GamblingNews.com. Online sportsbooks are being established at the provincial level, and private operators are entering the regulated markets, so Canadians are discovering new means to entertain, grasp, and make correct decisions in sports betting.
Widespread Adoption Across Provinces
The implementation of legal sports betting has varied across Canada’s provinces, but uptake has been strong in all jurisdictions. With its liberal licensing regime, Ontario has emerged as the most lively market in the country, thus enabling a multitude of private sportsbooks to compete. In the rest of the provinces, there are mostly platform operators controlled by the government; however, users are still in a state of rapid adjustment to the broadened offerings and new ways of wagering. As accessibility gets better, Canadians are becoming more aware of the distinctions between markets, bonuses, and betting styles, which makes the transition seem more like a logical continuation of their current sports habits.
Increased Engagement with Sports and Data
Legal betting has had an influence on how sports are consumed by a lot of Canadians. Fans are following gambling news, analyzing games in detail, checking lines more carefully, following injuries, and using statistics to make the best decision. The game-day experience has been expanded by betting, which has thus motivated fans to retain basic team loyalty. The rise of data-driven content, such as odds breakdowns, predictive analytics, and expert commentary, has been instrumental in making sports more interactive. Rather than being a passive viewer, a Canadian is now engaging more with the numbers, trends, and probabilities, thereby deepening his/her understanding of the games.
Growth of Responsible Gambling Education
As betting gets more and more exposure, a conversation about safe play is also getting louder. Gambling organizations in Canada have put in place a variety of measures and have devoted a lot of resources to making gambling more responsible and safer. Users have changed their behavior as well; they are now more aware of tools such as deposit limits, time monitoring, self-exclusion programs, and reality checks. Different provinces put a lot of effort into education first, thus helping bettors notice the signs of risky behaviour and learn how to stay within healthy boundaries. This cultural change is contributing to the normalization of responsible gambling practices instead of being treated as a mere intervention.
The Social Element of Modern Betting
Since the legalization of sports betting in Canada, it has become much more of a social activity. People in their friend circles now talk about their bets, share parlays, and watch matches together, thus creating a new level of fun. Social media is very much involved in it as bettors post their predictions, celebrate their wins, or explain their unfortunate outcomes. There are more and more online communities dedicated to betting discussions, where people find wagering as a mutually enjoyable pastime rather than a lonely one. The feeling of togetherness is what makes Canadians use betting as a part of their sports routine in a joyful and engaging manner.
Adapting to the Variety of Betting Options
With the legalization of sports betting in Canada, there are now more options available that go beyond the typical single-game bets. Live betting, player props, same-game parlays, and futures markets have all become elements of the modern betting landscape. Such a variety demands the adaptation of the bettors, and a considerable number of them are figuring out the operating principles of each type, the value of the times when they offer, and the manner in which odds change dynamically. In addition, bettors are becoming acquainted with such concepts as payout volatility, implied probability, and risk management. The learning curve is definitely there, but it has also resulted in a richer and more strategic betting experience.
Integration of Betting in Sports Media
Wide channels and sports networks in Canada have been very much on board with the advent of the betting boom. Playouts of betting lines are part of the pre-game shows, analysts are using betting language patently to highlight something on the field, and treat the sports betting companies as a partner to a team or a league for branded content. Canadians are warming up to the reality where the provision of betting information is just a normal part of their sports coverage. The change is considerable, and it can be seen as a transitory moment when betting moved from being a small niche topic to becoming a standard element of sports entertainment.
A Growing but Responsible Cultural Shift
Canadians, in the wake of legalization, see sports betting as one natural way to extend their love for sports while recognizing the necessity of self-control. Thanks to enhanced access, better education, and more transparent platforms, the whole betting experience has become safer, more enjoyable, and more a part of the daily sports culture. Canadians, as the market expands, are creating a scenario where gambling becomes a tool for deepening their connection with sports rather than a source of anxiety.
Features
How to Start Dating Online in Canada, Especially Ontario
Online dating in Canada can be genuinely effective, but only if you approach it like a simple process instead of a high-stress hobby. Ontario is a good place to date online because the population density (especially around the GTA) creates more active pools, while smaller cities still have enough users if you set your filters intelligently.
This guide gives you a practical Ontario-focused playbook: how to start dating online, what to set up, how to message, how to move to an actual date, and how to protect your time and safety.
Quick-start plan for Ontario singles
| Step | What to do | Ontario-specific example | Common mistake to avoid |
| 1. Pick your lane | Choose 1–2 platforms based on your goal | Toronto: nearly any major app is active; smaller towns: broaden radius to nearby cities | Downloading 6 apps and burning out fast |
| 2. Build a “real” profile | 4–6 photos + short bio + 2 prompts | Add a local hook: “Best coffee spot in Ottawa?” or “Best weekend day trip from the GTA?” | Only selfies, no bio, or “ask me” |
| 3. Message with intent | 1 specific question + 1 next step | “Coffee or a walk this week?” | “Hey” and waiting for magic |
| 4. Move to a date quickly | Suggest a public, simple meet | “30–60 minutes at a cafe near Union Station” | Texting for 3 weeks, never meeting |
| 5. Use safety rules | Public first date, own transport, tell a friend | Share date location + time with a friend | First meeting at someone’s home |
| 6. Filter hard, stay kind | End mismatches early and politely | “I’m looking for something more serious—wishing you the best.” | Debating obvious red flags |
1) Choose apps based on what you want (not what’s trendy)
Before you pick anything, decide your “dating intention” for the next 30 days:
- Serious relationship-focused: choose platforms where profiles have prompts, values, and more context. These tend to produce better conversations and clearer intentions.
- Casual dating / exploring: faster, swipe-heavy apps can work if you’re direct and you don’t take it personally when people vanish.
- International or broader discovery: consider platforms that make cross-border matching and messaging easy, especially if your local pool feels repetitive.
Ontario tip: if you’re outside Toronto or Ottawa, don’t assume “online dating doesn’t work.” Often it’s a settings problem. Increase your radius to include a nearby hub (for example, Hamilton, Kitchener-Waterloo, London, or the GTA), and be open to meeting halfway.
2) Build a profile that feels human (and gets better matches)
Your profile isn’t a résumé. It’s a conversation starter. The best profiles do two things:
- show what you look like, clearly
- show what it might feel like to date you
Photos: a simple set that works
Aim for 4–6 photos:
- One clear face photo (good lighting, no sunglasses).
- One full-body photo (normal setting, not a bathroom mirror).
- One lifestyle photo (hobby, cooking, gym, hiking, reading, music).
- One “social proof” photo (with friends is fine, but make it obvious who you are).
- Optional: a photo that shows your vibe (casual, dressed up, outdoorsy, artsy).
Avoid extremes: all selfies, all group shots, all travel photos, or filters that change your face. You’re not advertising perfection. You’re signaling honesty.
Bio: a 3-line formula that converts
Use this structure:
- Who you are: one sentence
- What you want: one sentence
- Local hook: one sentence
Example bios (Ontario-ready):
- “Ontario-based, equal parts ambitious and laid-back. Looking for a real connection with someone emotionally mature. Tell me your go-to comfort food or your favorite hidden spot in your city.”
- “New-ish to the area and building a life I’m proud of. I’m dating with intention, but I like things to unfold naturally. Coffee dates and good conversation beat endless texting.”
- “I’m the type who plans a day trip and packs snacks. Looking for someone kind, consistent, and curious. Bonus points if you like markets, walks, and laughing at dumb jokes.”
3) Messaging that doesn’t sound like a bot
Most conversations die because people write low-effort openings. Your first message should be:
- specific
- easy to answer
- slightly playful or warm
- connected to their profile
Openers you can copy
- “You seem like someone with good taste—what’s a perfect Saturday for you?”
- “Quick question: coffee first date or a walk first date?”
- “You mentioned hiking—are you more ‘short scenic trail’ or ‘full-day mission’?”
- “What’s the most underrated place in your city for a chill date?”
- “Two truths and a lie—go.”
A realistic mini-script to move toward a date
- You: “I’m enjoying this chat. Want to keep it simple and do coffee this week?”
- Them: “Sure.”
- You: “Great. I’m free Thursday evening or Sunday afternoon. Which works?”
In Ontario, many people appreciate directness because schedules fill up quickly (commutes, hybrid work, family obligations). Clarity reads as confidence, not pressure.
4) First date ideas that work in Ontario year-round
Plan dates that survive weather and keep pressure low.
Best first-date formats:
- coffee/tea (60 minutes is perfect)
- casual lunch
- market + snack
- walk in a busy, public area (only if weather is decent)
- museum/gallery (good for conversation breaks)
Ontario-specific practical tip: keep the first meet short and public. If it’s going well, you can extend it. If it’s not, you can leave politely without feeling trapped.
5) Safety and boundaries (the non-negotiables)
Online dating is normal. Basic safety habits should be normal too.
Do this every time:
- meet in public for the first date
- use your own transportation
- tell a friend where you’re going and when you expect to be done
- keep personal details (address, workplace specifics) private until trust is earned
Watch for pressure signals:
- pushing to meet at their home immediately
- refusing a simple video call but demanding quick trust
- love-bombing (intense affection very early)
- turning the conversation toward money, “business,” or investments
If someone reacts badly to your boundaries, that’s useful information. It means your boundaries are working.
6) Ontario realities: age and alcohol
If you’re dating in Ontario, it’s also helpful to know common legal basics: the age of majority is 18, and the legal drinking age is 19. If you’re unsure or you’re traveling within Canada, double-check local rules, but those are the typical Ontario standards people plan around (especially when choosing bars or venues).
7) A simple 2-week routine that prevents burnout
If you want progress without turning dating into a second job:
Week 1
- build a solid profile (one evening)
- swipe/message 15–20 minutes per day
- aim for 5–10 quality conversations, not 100 matches
- propose 1–2 simple dates
Week 2
- go on those dates
- adjust your profile based on who you actually liked
- tighten filters (age range, distance, intentions) to reduce noise
Online dating improves fast when you treat it like an experiment: test, learn, refine. You don’t need more apps—you need better signals, clearer messaging, and consistent boundaries.
If you want, tell me your approximate age range and whether you’re aiming for serious, casual, or international dating, and I’ll tailor the examples (bio + openers + first-date ideas) specifically for Ontario in the same format.