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A deep dive into the lives of some shadier members of our community

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

Wolfe Rabinovitch and his brother Milton, circa 1947. Wolfe counts $1,000 bills to give to his brother Milton to take to Canada “for a rainy day.” The Rabinovitches were originally from Morden, Manitoba. Photo taken from Jukebox Empire: The Mob and the Dark Side of the American Dream, by David Rainovitch. (Used with the author’s permission) Jukebox Empire will be published in October 2023.

“Caught between the Mob and the feds in a plot to save the casinos in Havana from Castro’s revolution, Wolfe Rabin pulled the biggest money-laundering scheme in history, but his hubris led to the conspiracy falling apart in a sensational trial. At a time when there was a jukebox in every restaurant, diner, bar, barracks, arcade, and canteen, Rabin’s trajectory from inventor to promoter to outlaw is set against the Mob’s growing influence of the jukebox industry. In a world of music, machines, and money, popular culture and organized crime collide in this true story of invention and greed. Rabinovitch pieces together the puzzle that begins in Chicago and spans the casinos of Havana and the financial giants of Europe, leading to what the FBI called “the biggest bank robbery in the world.”

“Rabinovitch is a winner of Emmy, Peabody, and Gemini awards. His significant films include the documentary Politics of Poison and the mini-series Secret Files of the Inquisition. Jukebox Empire is his first book.”

Of course, the moment I read that email I was interested in reading the book. Here we have some of the essential elements of a story that’s perfect for this paper: A crime story with a Jewish character at its centre – who comes from Morden, Manitoba no less!
I immediately thought of historian Allan Levine, who’s written extensively about Jewish characters with sordid backgrounds – especially in the bootlegging business, and contacted Allan to ask him whether he’d ever heard of this “Wolfe Rabin?”
Allan said he hadn’t previously, not that is, until he was contacted by the author, David Rabinovitch, who asked Allan for some help.

After I began to read the book, however, I was again contacted by the publicist, who asked me to withhold writing a review of the book until October, when the book will be released to the public.
But, to whet readers’ appetites even further, here are some endorsements David Rabinovitch has already received in advance of the book’s actual release to the public:
“A fast-paced, colorful romp through a slice of the twentieth century American underworld”
-David Kertzer, Pulitzer Prize winner
“Jukebox Empire reads like a novel but the characters and events are real and chilling.”
-Peter Edwards, co-author, The Encyclopedia of Canadian Organized Crime
“It has everything: action, incredible characters, suspense, humor. Can’t wait to see the movie.”
-Fred Fuchs, producer, The Godfather, Part III
“A compelling story of family and crime that touches on key events of U.S. history in the 1950s and 60s”
-Scott M. Deitche, author, Garden State Gangland
“An eye-opening, informative, and fascinating book. Jukebox Empire is must-read.”
-Antonio Nicaso, author, Made Men, The Dark Mafia, Angels Mobsters & Narco-Terrorists
“A delightfully entertaining story of jukeboxes, money laundering, and stolen bonds.”
-Alex Hortis, author, The Mob and the City
“A unique combination of family memoir and investigative journalism.”
-Gary Jenkins, producer/host, “Gangland Wire”
“A tour-de-force account of the Mob’s growing infiltration into legitimate American industry and how it affected one man who was obsessed with power and money at all costs.”
-Joe Saltzman, Prof. of Journalism, Annenberg School of Communication, University of Southern California

I also asked David Rabinovitch whether readers could order Jukebox Empire in advance, so that they could obtain a copy as soon as it’s released.
David responded: The book “is available for pre-order online through the website www.jukeboxempire.com (Chapters Indigo in Canada) or readers should request it at their favourite bookstore.”

Al Smiley Also originally from Winnipeg, Smiley was best of friends with Benjamin (Bugsy) Siegel. Smiley was sitting next to Siegel on Siegel’s living room couch in June 1947 when a gunman shot and killed Siegel, firing through the living room window.

All this got me to thinking: Over the years, we’ve published quite a few stories about Jews with mob connections, and some of those individuals came from Winnipeg. Perhaps the story that elicited the most interest was one we published in 2015 by Martin Zeilig about a character by the name of Al Smiley. (You can still find that story on our website’s online archive. Just search for “Al Smiley.” in the “search archive” button on jewishpostandnews.ca)
Smiley, it turns out, was best friends with Bugsy Siegel (whose real name was Benjamin – and who hated being called “Bugsy.”) In fact, Smiley was sitting right beside Siegel – on his living room couch in his Las Vegas home, when Siegel was shot and killed by a Mafia hitman.

That story led to another story about a mobster with a Winnipeg connection who, it turns out, was actually related to me in a very distant way, someone by the name of Harry Altman.
In 2020 I wrote about someone by the name of John Novick in an article I wrote about the children of Jewish mobsters. In that same article I referenced Myer Lansky and his daughter, Sylvia, who was the subject of one of the greatest interviews Anna Maria Tremonti ever conducted when she was host of CBC’s “The Current.” (You can still listen to that interview on the CBC website.)

Finally, a few years back I happened to attend a Fringe show which was titled “Davey the Punk.” The creator of that show – and its sole performer, was singer Bob Bossin (who was a member of a well-known group called “String Band.”) The show was about Bob’s father, Davey Bossin who, while not a “made man” per se (Mafia parlance for someone who is accepted into the Mafia), but who was very “connected” and about whose background Bob Bossin knew nothing until years after his father had died.

What’s my obsession with mobsters, you might ask? Well, I don’t think I’m much different than a great many others when I say that I’m both fascinated and repelled by all these figures – and the fact they’re all Jewish only adds to my interest.

But, it got me to thinking – once again: Where are the stories about Winnipeg Jewish hoodlums from the North End? Even in Russ Gourluck’s masterful history of Winnipeg’s North End, The Mosaic Village, he only mentions two shady characters: Stanley Zedd, a well-known operator of gambling establishments, especially the Margaret Rose Tea Room on Osborne, and Bll Wolchuk, a major bootlegger in the 1920s.

Ernie Chisick One of the most authoritative sources on “shtarkers” (strong guys) and assorted individuals from the North End who had somewhat unsavoury reputations


So – to find out more about Jewish hoodlums of a bygone era, I turned to my most trusted source on the subject: Ernie Chisick, whom I first met at the Y reunion in 2019.
For those who don’t know Ernie – he is a raconteur of the first order and his own brushes with the law when he was younger only add to his mystique.

I sat down with Ernie one recent evening and asked him to repeat some of the fabulous stories he’s told me over the years about colourful North End characters with whom he crossed paths over the years. I was especially keen on hearing Ernie recite some of the nicknames of guys with whom he associated when he was younger.
The problem is, as Ernie explained, some of those individuals are still alive and, even if they’re not, they have kids and grandkids, so referring to them by their full names might not even be embarrassing, it might be potentially lethal for me!
I have attempted to reach out to one character in particular who, as Ernie described him, probably knows more about Jewish hoodlums… and criminals, from the North End of the 40s and 50s than anyone else alive, but even if that guy does get back to me, I rather doubt he’s going to want to see his name end up in the Jewish paper in Winnipeg. (I’m hoping that he will respond to my message and I’ll promise him full anonymity if he’s prepared to talk about his former friends – who weren’t quite boy scouts.)

Ernie though, has too many good stories not to at least refer to some of them here. He told me about a gambling club on Selkirk Avenue between Salter and Powers that was run by an individual who was known as “Montreal…..” (Again, I’m leaving out the surname because it’s a name that would be familiar to at least some readers.)
According to Ernie, that club had a lookout by the name of “Srulik Flaxman.” When Srulik would spot a cop coming, he would shout to the guys who were in the back room: “Watch out – it’s the football shoes kimmen!” (Why he referred to cops as “football shoes,” Ernie didn’t know.)

Here’s another story Ernie tells – about a character who went by the name “One-eyed Connolly.”
“They’re playing cards,” Ernie says, “and Connolly says he’s got to take a piss.” But before he gets up to go to the bathroom, he leaves his cards on the table, then takes out his glass eye, puts it on the table, and says to the eye: “Watch them guys; they’re all a bunch of thieves!” Apparently that so unnerved the other players, they sat there frozen in their seats, afraid of that well-known Jewish superstition: “the evil eye.” (But Connolly wasn’t Jewish. Can a non-Jew threaten someone Jewish with the “evil eye?” There’s a Saturday morning sermon for you, all you rabbis and would-be rabbis out there.)

With reference to Stanley Zedd and the Margaret Rose Tea Room, Ernie says that his father, Charlie, once said to him, “Take this to the Rosie (the nickname for the Osborne Tea Room) and ask for Stanley Zedd.” Charlie handed Ernie a paper bag (which, Ernie now says, unbeknownst to him at the time, contained betting slips. Ernie claims he was only an innocent 16-year-old. not yet wise in the ways of the world. Anyway, the statute of limitations protects him now.)
So, Ernie drove to the Tea Room and announced, when he walked into the room, “I have something for Stanley from Charlie.”
He was ushered into the back room where Stanley Zedd held court. “He was very nice to me and told me my father was an honourable man,” Ernie recalls.
Another time, Ernie says, he got a phone call from his father in the middle of the night.
“Charlie,” Ernie asked (Ernie says he always called his father by his first name), “what is it?”
“I’m in jail,” Charlie responded. (He didn’t say why.)
“In the morning,” Charlie continued, “give Roland Penner a phone call.” (Roland Penner would go on to become Manitoba’s attorney general, but at the time he was in partnership with Joe Zuken in the firm, Zuken and Penner.)

“So, I phoned Roland Penner’s office in the morning. I told his secretary who I was and she put me through immediately to Roland Penner.”
“Roland says to me, ‘You heard from your dad? The mounties made a raid in the middle of the night. Eighteen guys (from different cities) were charged with conspiracy to commit bookmaking.’”
“Roland says: ‘I’ve got something for you.’ “ He explained that the mounties took Charlie out in the middle of the night and it was quite cold.
“Your father wanted me to give you his gloves,” Penner continues.
“I put them on,” Ernie says, “and I feel a lump in one of the gloves. They were betting slips that could have been used as evidence in court.’
(Did Penner know that, I wonder? Ernie says he doesn’t know.)
“All the guys were taken to a lock-up in Calgary. Harry Walsh represented the three Winnipeggers,” Ernie continues.
“My dad explained that the Jewish boys were able to get kosher food to eat because one of the mounties was Jewish and he brought them deli.”
The Grey Cup was being held that week, Ernie says. “Charlie said he made $10,000 taking bets on the game” – while he was in jail.
Eventually, when the accused were brought to trial, they were all acquitted, Ernie explains.
“Walsh said they weren’t betting with each other; they weren’t in business together.” As a result, the conspiracy charge didn’t hold up, Ernie says. (If they had simply been charged with bookmaking, then the likelihood is that at least some of them, including Charlie, would have been found guilty.)

I don’t necessarily approve of Charlie’s behaviour. Rather, the stories about the less savoury aspects of Jewish lives don’t usually receive much attention in North American Jewish newspapers. (Some Israeli newspapers, in contrast, are not at all reluctant to publish extensive investigative pieces about the Israeli underword.)Yet, there are so many colourful stories to tell I thought I’d deviate from the Gerry Posner and Myron Love types of stories that extol the virtues of individuals who have led honest, hardworking lives to write about other less honourable fellows who, as the late Harvey Rosen used to say are “of the Hebraic persuasion.”

We’ll have more about members of our community who had connections to activities that were not always on the right side of the law in our Aug. 16 issue. If you might have a story to add about a relative with a shady past that you might like to share, you can email us at jewishp@mymts.net

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Musings from Dizengoff Street – by Bruce Brown

(August 8, 2026)

Outside Basimta Café in Central Jerusalem.  Love the red shirt against a tiny sea of black.  Not sure I am shrugging because of the ultra-orthodox uproar over a Jerusalem café operating on Shabbat or the lack of an ultra-orthodox uproar over a Jerusalem café operating on Shabbat.  For the last six weeks Israeli headlines shouted about the cafe chaos.  With the ultra-religious blocking entrances and storming the café.  While shouting ‘Shabbos!  Shabbos!’   Upsetting the secular amongst us just wanting to enjoy our Saturday iced matchas.  So the wife and I thought we would check it out.  And.  Yes.  Buy something to support the business.  Uproar.  Not.  Blocked entrances.  Not.  Storming the café.  Not.  Albeit there were police barriers separating the devout protesters from the coffee drinkers.  The protesters being just a few dozen black clad, pious Jews.  Mostly teenagers.   And yes.  Shouting ‘Shabbos!  Shabbos!’  Certainly underwhelming in its reported mayhem.  Reminds me of the famous saying misattributed to Mark Twain – “If you don’t read the newspaper, you’re uninformed.  If you do, you’re misinformed.”  But I did enjoy my iced matcha.

(August 6, 2026)

Here we go again.  Another round of forever negotiations.  As someone who negotiates for a living.  The way things are going in the straits.  If I had to recommend a book on the subject to a new hire.  Between The Art of the Deal, A Presidential Edition by Donald J. Trump or The Real Art of the Deal by the Mullahs of Iran with a special forward by the IRGC. Well.  I would choose the latter.

(August 3)

Bravo Yoav Segalovitz, Liberal Yesh Atid MK and Monsour Abbas, United Arab Ra’am MK and party head.  For breaking a glass ceiling where a Jewish lawmaker joins an Arab political party.  No less a political earthquake in my little shtetl.  Which can significantly impact coalition block arithmetic and posturing and strategy in the upcoming elections.  Now Ra’am can be considered a legitimate ‘Zionist’ partner when forming coalition blocks and potentially pushing the ‘center left/right’ party over the 60 seat majority threshold.  In our crazy parliamentary democracy defined by a multi-party (about fourteen!!), proportional representation system.  To paraphrase Winston Churchill, Israel’s proportional representation model of governance is the best parliamentary democracy system except for all other forms of working democracies.  Stay tuned for more amateurish political musings as we move towards Israel’s 26th national election – five of them held since 2019. 

(August 1)

Although both sides say they are open to diplomacy.  Neither really trusts the other.  And American military action, or its threat, continues.  I read headlines in the middle of the night -it’s a nervous habit lately– that the Dynamic Duo of Trump and Netanyahu may again strike in unison.  Possibly this weekend.  Yikes!  Prompting me, at 2:30 AM, to dash around the house stocking my safe room.  Bottled water.  Canned food.  Medicines. Documents. The beat goes on….

If it’s crazy here.  It’s insane in Italy.  With a recent online ‘Jew Hunt’ in the Milan area.  Before being removed, the digital forms urged reportings of Israelis and Italian Jews staying in local hotels.  The infamous Global Sumud Movement -yes, the one coordinating ‘peace and humanitarian’ flotillas to Gaza- was somehow connected.  Although they deny involvement?!  This deranged decree was looking to identify Zionist tourism and Zionist neo-colonization in Italy.  I’ll stick with stocking the saferoom.

Then there’s New York Mayor Mamdani, a Global Sumud Movement supporter, threatening to arrest Prime Minister Netanyahu if he comes to New York.   But since discovered he has no legal right for such a grandstanding, antisemitic, anti-Israel, anti-Western, anti-democratic antic.  Maybe Mandami should be arrested!  Or at least impeached.  For being a grandstanding, antisemitic, anti-Israel, anti-Western, anti-democratic mayor.


Here’s a post Bruce sent us Friday, July 31:
WARTIME MUSINGS

Should credible threats against FLOTUS and ‘FSOTUS’ (first son..) not be justification to attack first.

As for yesterday’s summit. Netanyahu really can’t win. Explainer. If Trump now attacks without victory its ’cause of Netanyahu. If Trump now attacks with victory its ’cause of Trump. And, in Israel, if Trump doesn’t attack -victory or not- Netanyahu failed in his eighth meeting with Trump. And if Trump does attack -victory or not- half the country will vilify Bibi anyway. Missing a permutation?

Ya. I know. Kinda’ need a definition of victory for that musing to work.
And here in my little shtetle. We go to sleep unsure if there will be a code red in the middle of the night. And if not. We wake up thinking it will be tonight. How do you define stress?

Seemed like an appropriate way to end this musing.

Bruce Brown is a former Winnipegger who made aliyah to Israel over 35 years ago. Bruce first began writing for us – in his own inimitable style, in 2012, during what was known as “Operation Pillar of Defense.” His occasional musings on aspects of life in Israel that were far from what you’d typically read in other reports from Israel were hugely popular – both in the print Jewish Post & News and on this website.
We’re now glad to report that Bruce is back writing for us – this time on a regular basis. We will post Bruce’s reports as they arrive – with the date of each post at the beginning of that post.
Here’s
some information about Bruce – and awards he’s received for his writing:

Bruce Brown.  Canadian born.  Now living in Israel (for a long time).  Bruce works in Israel’s hi-tech sector by day and, in spurts, is a somewhat inspired writer by night.  He received the American Jewish Press Association’s award for writing excellence in 2019 and 2025.  And wrote the 1998 satire, “An Israeli is….”  Bruce’s musings are political, social, economic and personal.  With lots of biting, contrarian, sardonic and irreverent insight.

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