The Most Famous Canadian Blackjack Players of All Time

Published Date: 23 May, 2022 Updated date: 25 May, 2022 By Phil

One way of getting to learn more about blackjack is by studying some of the individuals that have made it to the blackjack hall of fame.

One way of getting to learn more about blackjack is by studying some of the individuals that have made it to the blackjack hall of fame. While some successful blackjack players prefer remaining anonymous, others take pride in their success and achievements.

Vocal blackjack veterans often use their pen names to author blackjack gaming books. Others have retired from the game completely in a bid to enjoy their fortunes.

In this guide, we will look into some of the most famous Canadian blackjack players in the game’s history. If you are looking for reliable Canadian online blackjack sites, check them at

Monica Reeves

The 50-year-old Monica Reeves is considered the loveliest professional gambler in Canada. Having grown up in Oakville, Ontario, Monica developed a passion for card games at quite an early age. Her family’s game nights were always her favorite family moments.

Little did Reeves know that decades later, her name would read on the list of top players in one of the most popular card games, blackjack. Besides her early interest in the game, her high intelligence has also helped her win big in the game.

While Monica trained and practiced as a dental hygienist, she would soon move to the modeling industry to showcase her immaculate beauty. A few years into her modeling career, her childhood passion for card games caught up with her.

However, Monica’s confidence was often lacking, making her hesitant to join tournaments. Eventually, she decided to hire a tutor, Jim Worth. Together, they took a year off to hone Monica’s skills before joining the 2005 APT Aruba Poker Classic.

She managed to finish 114th out of 644 participants, earning $5,500 from a $5200 buy-in. While many people might consider a $300 win from such a tournament insignificant, it was a big deal for Monica because it was nonetheless a profit in her first attempt.

That gave her confidence and over the course of the next five years, Monica cashed in over $40,000 from multiple events.

Monica’s Shift to Blackjack

In 2006, Monica came to learn about a CBS television series where the world’s top blackjack player would participate in an elimination tournament. She quickly seized the opportunity and began getting ready to participate

She won the fourth UBT tournament, bagging a spot in the first Ultimate Blackjack Tour Champions Tournament. She managed to finish 7th in the championship event. Monica also participated in the UBT ladies’ event, where she narrowly lost to Jennifer Tilly.

Brian Zembic

Born in Winnipeg, Manitoba, Brian Zembic has always had a prevalence for card game gambling. Zembic’s first pro-blackjack moment was when he participated in the second season of the World Series of Blackjack. Unfortunately, he was eliminated in the 9th round.

One day in 1996, when Brian was having a rough day and short on cash, he made a daring bet with one of his buddies. Jobo, the friend, wanted to see how far Zembic was willing to go for $100,000.

Jobo offered to give his long-time buddy $100k if he gets C-cup breast implants. Please note that we are not talking about stuffing water balloons in a bra, no. Brian had to undergo plastic surgery and keep the implants for not less than a year to win the bet. Zembic took the bet and received his $100k payout.

That was not the last time that Zembic gambled on a crazy stunt. The champ once collected $3000 for running through the streets of Philadelphia in a woman’s panties and bra, sporting the new c-cup breast! At another moment, he had to live in a cardboard box outside his backgammon club to collect $25,000.

Brian Molony

Molony is from Toronto, Ontario. He is considered among Canada’s most popular gamblers, but not for the best of reasons. Most people came to learn about Molony from the news in April 1982 after he got arrested for embezzlement charges.

Others came to learn of Molony’s infamy after Philip Seymour Hoffman portrayed him as Dan Mahowney in the 2003 film Owning Mahoeney.

Molony developed an unhealthy love for gambling at a tender age. He began attending racetrack at the age of 10. Upon graduating from college with a degree in journalism, he decided to pursue his dreams of becoming a financial underwriter.

Hungry and Desperate Molony

Molony landed in a management training program with the Canadian Imperial Bank of Commerce. Before long, he was part of the 1,600-branch network, learning all the organization’s in and outs including inevitable weaknesses.

He later began embezzling huge amounts of money by approving loans for fictitious companies and transferring the cash to a holding corporation, which was the parent company of the Las Vegas Casino, Desert Palace.

Using this ploy, Brian Molony managed to embezzle and gamble over $10 million across different casinos in the US.

On the 26th of April 1982, Molony lost over a million dollars in a single gambling day at the Caesar Hotel & Casino in Atlantic City. He was arrested the following day and investigations revealed that he had gone on an 18-month gambling spree.

He became progressively brazen and exorbitant in his gambling during this period. Upon being arraigned in court, Molony pleaded guilty to embezzlement charges and was sentenced to two and a half years in prison.

Ken Uston

Uston is yet another famous blackjack player and author who has found his way to the top of the blackjack hall of fame. Ken is particularly famous for coming up with the idea of team play in card counting.

Ken and his buddies won millions of dollars from casinos in the ‘70s by using this technique. He is also popular for having been banned from multiple casinos for trying to thwart their brands through his clever deployment of disguises.

Tommy Hyland

Hyland is known for his Hyland Team of Card Counters. The team has been in operations since 1979, with several wins under its belt. The team launched with just four members and an investment of $16,000. A year later, they had won $30,000.

Hyland was once arrested in Canada for cheating. However, he won the court battle. Tommy Hyland’s legacy is built on him being a great mathematician and team leader. He holds the ability to build loyalty and trust among team members.

Category: Lifestyle