Drake, Norm Macdonald Among Canada’s Most Famous All-Time Gamblers

Written By Martin Derbyshire on March 22, 2022
Canada Most Famous Gamblers Drake Norm Macdonald

Gambling options for Canadians will increase exponentially when Ontario opens up its online gambling market.

Private online casino apps and sportsbooks will launch in the province starting on April 4.

If it isn’t obvious already, it will show itself soon enough in the money flowing into those sportsbooks and casinos — Canadians truly love to gamble. And many of us have a soft spot for gamblers that put it on the line in bold, big-moment bets.

In honour of that, we’ve profiled just a few of the country’s most famous, biggest, and all-time greatest gamblers.

Haralabos Voulgaris: From airport skycap to NBA front office

Haralabos Voulgaris is a true sports betting legend. He went from being a student at the University of Manitoba and skycap at the Winnipeg airport betting the ponies at Assiniboia Downs, to a whale at Las Vegas sportsbooks who successfully bet over $1 million a day on the NBA.

In fact, he was so good at finding and exploiting edges in basketball games, the NBA’s Dallas Mavericks hired Voulgaris as the team’s director of quantitative research and development.

Voulgaris’ first big betting successes came when the CFL moved south, expanding to as many as five US teams in the early 1990s. He was able to exploit the fact that sportsbooks failed to account for many of the US teams playing on smaller NFL-sized fields instead of the longer and wider fields used in Canada. His bets grew from $100 to $200 at the start of one season to $2,000 and $3,000 by the end of it.

Voulgaris reportedly built his original NBA betting bankroll by betting all of his $80,000 life savings on the Los Angeles Lakers winning the 1999-2000 NBA title at +650 (7.50 European equivalent).

A 2013 ESPN the Magazine story claims Haralabos turned that half-million-dollar win into a million with the same bet a year later. Then, he built it into millions more exploiting halftime NBA totals lines beginning in 2002. Apparently, sportsbooks were failing to account for big scoring in the fourth quarters of close games thanks to an increased number of free throws, sped-up play and clock management.

Voulgaris: I had trio of NBA coaches ‘nailed perfectly’

The story also says Voulgaris exploited a similar edge found specifically in the way coaches Eddie Jordan, Jerry Sloan and Byron Scott managed games. He was quoted in the story saying:

“Those were three coaches I had nailed perfectly. I knew exactly what they were going to do. I mean, it was a joke, it was so easy.”

It took two years before sportsbooks made the proper adjustments. After losing a third of his bankroll over half an NBA season, Voulgaris turned to computer modeling, algorithms, statistical analysis, probability and quantitative theories. He also increased his betting frequency while decreasing his betting amounts. That lowered his return on investment but ensured continued growth.

Haralabos hires help, leads to ill-fated Mavs job

Voulgaris hired a math prodigy to help him build a new NBA betting computer model. By 2008, it was crunching the numbers well enough to make him a big winner with smaller bets. Then, ahead of the 2009-10 NBA season, he quit using it to gamble and signed on to consult an NBA team. The job only lasted five months, but it sewed the seeds for what was to come.

Voulgaris and the NBA betting computer model he called “Ewing” won millions more over the next eight years. Along the way, he earned $3 million more in live poker tournaments and untold millions more via cash games and bets with private individuals.

Then, the Dallas Mavericks came calling in 2018. Depending on who is asked, Voulgaris became either the de facto GM of the Mavs or an ego-driven blowhard who believed he should be. Either way, the Winnipeg, Manitoba native left the team and was back to betting, continuing to build his ever-growing sports betting legend by 2021.

Norm Macdonald: Once, twice, three times gone broke

Norm Macdonald was a Canadian comedy legend who did stand-up, acted and wrote for a number of TV shows and films before his 2021 death. Along the way, Macdonald was a poker enthusiast who played the game whenever he could and regularly bet a lot on sports.

Norm Macdonald

He was a writer for Roseanne before joining the cast of Saturday Night Live. Macdonald spent five seasons there, including three and a half as the Weekend Update anchor. He wrote and starred in the film Dirty Work and had his own sitcom, The Norm Show, for three years. Macdonald’s deadpan style was enjoyed by millions and many consider him to be one of the best late-night talk show guests ever.

Macdonald was also a prolific voice actor, hosted a number of his talk shows, and once wrote a fictionalized biography loosely based on his life. The comedian died from leukemia in 2021, but not before leaving a legacy as a comedy giant, sports bettor and poker player.

Macdonald was a legit poker player

The Quebec City native regularly competed at the World Series of Poker in Las Vegas, regularly appeared on Poker TV shows like Poker After Dark, and was reportedly a fixture in many high stakes Hollywood home games. According to the Hendon Mob poker database, Macdonald had $54,019 in career live tournament earnings. His WSOP Player Profile shows four official World Series cashes, including three for $17,461 total at the WSOP, dating back to a deep run in 2007, and one cash on the WSOP Circuit:

  • 2019 50th Annual World Series of Poker $400 COLOSSUS (Event #61): 1336th for $689
  • 2019 50th Annual World Series of Poker $800 No-Limit Hold’em Deepstack 8-Handed (Event #53): 236th for $2,164
  • 2018/19 WSOP Circuit – BICYCLE CASINO (Los Angeles) Event #13: $250 No-Limit Hold’em: 27th for $520
  • 2007 38th Annual World Series of Poker Event #28: $3,000 No-Limit Hold’em: 20th for $14,608

Macdonald’s Hendon Mob profile also shows a final table appearance in a $1,000 No-Limit Hold’em event at Bellagio in Las Vegas back in 2006. He finished third for $20,915.

Plus, he has two wins at Recurring Tournaments at Aria Resort & Casino, including:

  1. Apr. 23, 2019 $110 + 30 No-Limit Hold’em for $2,044
  2. Jan. 10, 2013 $100 + 25 No-Limit Hold’em for $2,241

The tournament winnings don’t amount to much. But they date back to November 2003 at the World Poker Tour’s Hollywood Home Game. That proves Macdonald took poker relatively seriously for at least the last two decades of his life after reportedly taking it up at age 15.

Of course, Macdonald cemented his legacy in the poker world in 2011 when he replaced Gabe Kaplan as the host of High Stakes Poker on Game Show Network. That version of the show ended after what was its seventh season. PokerStars had become the official sponsor and pulled out of the US market that year, ending funding for the show. High Stakes Poker returned for an eighth season on PokerGO in 2020 with Kaplan coming back as host.

Norm live bet golf on Twitter before it was cool

McDonald also spent the last decade of his life regularly live-tweeting sports on Twitter. He once told a USA Today reporter he did it because he loved the drama of sports and yearned to be a sportswriter. Macdonald said he was big on golf betting, having bet Tiger Woods to win two majors that season at 36-1. Plus, he claimed he’d won a lot of money betting on the NFL the week of that interview, saying:

“I put the Chargers and Eagles on every parlay this week and won a fortune.”

Notably, as Norm told Marc Maron on an episode of his WTF podcast, McDonald also went entirely broke (“dead broke”) three times when he “actually had a lot of money.”

Leblanc brothers: Window washers pound parlays, take on taxman

Brothers Brian and Terry Leblanc are as famous for beating the house as they are for beating the government and clearly defining how Canada taxes gambling and lottery winnings.

According to a Globe and Mail profile on the pair, the Leblancs were sports fans working as window washers for their father’s business in the late 1980s when they won close to $90,000 betting the ponies at Woodbine Race Track in Toronto.

Then, they struck a plan to start betting on sports with the money via the Ontario Lottery and Gaming Corporation’s Proline parlay betting sports lottery product when it launched in 1992. The brothers lost close to $10,000 that first year. But it wasn’t long before they started winning, and winning big.

$5.5 million haul in longshot sports parlays? $12 million?

By the mid-1990s they’d moved to Aylmer, Quebec, which straddles the Ontario-Quebec border near Ottawa, so they could place bets via Proline Sportsbook and Loto-Québec’s Mise-o-jeu. By then, they were betting between $200,000 and $300,000 a week and had turned a part-time sports betting hobby into what looked like a full-time business.

Forced to bet parlays via provincial lotteries, they bet as much as they could on the biggest ones with the longest odds. Most of the time, they lost. But the Globe and Mail says they hit it big a few times, including three $1.7-million paydays (two in January and February of 1996, another in 1999).

In total, the Globe and Mail says the Leblanc’s earned close to $5.5 million from 1996 to 1999. Other stories on the brothers claim they may have beaten provincial lotteries for upwards of $12 million overall. The Leblancs themselves have estimated they were earning around $20,000 a week in the 1990s.

OLG fights back, imposing Leblanc limits

Then, the OLG fought back. It reduced personal betting limits on Proline from $5,000 to $100 a day. The group also told lottery retailers they could only take in a maximum of $32,500 in bets each day. They may have even told certain Aylmer retailers not to take the Leblanc’s bets anymore.

That’s when the Leblanc’s started paying runners to place $100 bets at dozens of lottery retailers all over the province to get their $200,000 to $300,000 in bets down every week.

Plus, they hired a lawyer to go after the OLG, claiming the betting limits unfairly targeted them. They claimed limits were only being enforced in the Ottawa area where they were betting.

OLG officials simply claimed Proline wasn’t meant for professional gamblers or big-time sports betting operations like the Leblancs. The lower limits just ensured the games were reserved for recreational bettors to maybe win a few bucks.

Not so suddenly after that, the taxman came calling.

The taxman cometh, but Leblancs set a precedent

The Canada Revenue Agency sent the brothers a notice of reassessment claiming that because they used a betting system, managed all the betting on a computer, placed a huge volume of bets, and paid people to help them get all the bets down, this was a business that should have to pay tax.

In their fight to get the betting limits removed, Brian Leblanc told Maclean’s magazine he and his brother used complex math to calculate probabilities and took advantage of the lottery corporation’s mistakes. But when the case went to tax court in 2006, the Leblancs claimed they only used computers to calculate the odds and the bets were just guesses.

The Leblancs said luck was their only system and since gambling winnings aren’t taxable in Canada, they didn’t owe Canada Revenue a thing.

A Tax Court of Canada judge agreed, saying Canada Revenue had no proof a betting system was used. The court said a large volume of bets isn’t enough to prove the Leblancs were running a business.

Judge rules brothers are compulsive gamblers, not cheaters

Justice Donald Bowman also said the Leblancs:

“Bet massively and recklessly and in those games where they could, they bet on long shots. Certainly it meant that if they won they won big, but the converse is that if they lost, they lost big and, given the astronomical odds against winning, their chances of losing were far greater than their chances of winning.”

Ultimately, he said the whole thing made the brothers compulsive gamblers, not business operators. Therefore, the gambling winnings they had amassed were not subject to tax.

It was a win for gamblers all over Canada, proving luck is not subject to any tax in this country. Plus, it made Brian and Terry Leblanc Canadian gambling legends.

Drake: DeepPockets6 bets $1 billion offshore

Earlier, PlayCanada reported that between Super Bowl wagers, UFC bets, and some massive online roulette spins, Toronto hip hop legend Drake had gambled over $1 billion in just a few months on the unregulated offshore Bitcoin casino and sportsbook site Stake.

It turned out all this massive action was leading somewhere, as the Drake-Stake partnership became official on March 1 when Drake announced he’ll be taking part in a live streaming gambling event on Stake in the near future. Stake now lists Drake as an official partner.

Stake is considered an offshore sportsbook here, since it’s licensed in Curaçao, not Ontario.

Plus, Stake is a Crypto casino and Sportsbook that accepts Bitcoin. The Alcohol and Gaming Commission of Ontario says the new privately-run and provincially licensed online casinos and sportsbooks coming in April won’t be allowed to. That means Stake isn’t about to get licensed in Ontario.

So, all of Drake’s recent action has not exactly been of the legal, regulated, above board type.

But, that doesn’t make it any less notable.

Roulette is Drake’s game of choice

It all started with a number of Instagram posts featuring Drake at the online roulette tables.

It heated up when the massive Toronto Raptors fan posted pics of himself playing online roulette during a game from his courtside seats at Scotiabank. He said he may as well, since there was space for his laptop on the seat next to him because Covid protocols limited attendance to 500 people.

Soon after, Drake got into a very public battle with UFC fighter Colby Covington. The rapper bet $275,000 on Jorge Masvidal against Covington in the UFC 272 headliner. And, when Covington won by unanimous decision, he addressed Drake’s bet in the post-fight presser, saying:

“Let’s talk about all the money that Drake lost tonight. He needs to go back to selling those sh*tty albums to make back the money.”

Drake’s action appeared to peak when he placed $1.6 million in Super Bowl LVI bets in February. He bet $600,000 on the Rams to win, $500,000 on Odell Beckham Jr. to score a TD, and $500,000 on Beckham to net at least 62.5 receiving yards. Drake won all but the last bet, returning him $1.981,000.

But, the big story came from Our Generation Music. The hip-hop news outlet posted a screenshot of Drake’s ‘DeepPockets6’ Stake account showing that since Dec. 28, 2021 he has placed 7,498 bets worth some $1.531 billion in Canadian dollars or 28,459 in Bitcoin.

These are the kinds of numbers legends are made of, for better or worse.

Photo by Sue Ogrocki / Associated Press
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Written by
Martin Derbyshire

Martin Derbyshire has more than ten years of experience reporting on the poker, online gambling, and land-based casino industries for a variety of publications including Bluff Magazine, PokerNews, and PokerListings. He has traveled extensively, attending tournaments and interviewing major players in the gambling world.

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