Canada’s luckiest lottery winners who beat the odds twice — even three times

There’s lucky, and then there are these Canadians who won the lottery twice — some, even three times.

Have you always dreamed of winning the lottery? According to OLG, your odds of winning the Lotto Max jackpot aren’t great at 1 in 33,294,800. Of course, those odds vary depending on the game.

But while most of us can’t even win a Free Play, these lottery players have defied astronomical odds, leading to life-changing wins on multiple occasions. Meet this year’s multi-time lottery winners who appear to have luck on their side.

lottery

OLG

Vincent Charlemagne certainly knows his way to the prize centre, having won the lottery a staggering three times. In August 2013, the self-employed contractor won the Lotto Max jackpot worth $30 million.

“I thought I won just a couple bucks,” he said.

Then, in February 2021, he won a Maxmillions prize worth $1 million.

Three years later, Charlemagne found himself at the OLG Prize Centre for the third time after winning an Encore prize worth $100,000 in the August 9, 2024 Lotto Max draw.

Now retired, the lottery winner from Thornhill, Ontario, said, “I am happy and comfortable. I definitely won’t be working anymore.”

lottery

OLG

Betty-Jane Novelletto isn’t new to winning. The lottery player from Essex, Ontario, celebrated her first big win in 2011, nabbing a $100,000 Lotto Max prize.

This year, Novelletto said she was on her way to pick up her car when she decided to check her tickets on the OLG app. As she did so, she heard an announcement on the radio that someone in her area had won $1 million.

“I said out loud, ‘That’s me!’” she recalled.

Novelletto said she’ll invest her windfall and plans to buy a Jeep.

lottery

WCLC

When asked how it feels to win the lottery for the third time in one year, David Serkin, a resident of Lethbridge, Alberta, said, “It’s just unbelievable. It feels good — it always feels good!”

Serkin’s first big win was $250,000 twelve years ago. His second big win was a $500,000 prize in the August 20 Lotto Max draw.

He couldn’t believe his luck when he discovered he had won $1 million in the November 16 Lotto 6/49 draw.

“I saw there had been a win in Alberta,” he said. “And this time, it was my ticket!”

Serkin said he has been using his previous prizes to help family and friends. This time, he and his wife are returning to Maui, where they spent their honeymoon.

“You’ve got to keep your wife happy, and I’ve been doing it for decades,” he said.

lottery

OLG

After claiming a $10,000 prize with The Big Spin in 2021, Olympia Richards did not realize she would return three years later after winning an even bigger prize.

The bank branch manager from Pickering, Ontario, was at home enjoying a cup of coffee while playing her Instant Majestic ticket when she found out that she had won $50,000.

“I immediately started shaking! All I remember is screaming with joy, telling my husband, who was in the bathroom, to hurry up,” she recalled. “All we could do was stare at the ticket in pure disbelief.”

Richards said she’ll use her winnings to pay bills and treat herself to a trip to Las Vegas.

lottery

WCLC

Calgary resident Osman Adam is now a multimillionaire after celebrating his second, even bigger lottery win.

Adam won a $1 million Lotto Max prize in May 2021, which he used to buy a house and a vehicle. He found himself at the prize centre again this year after winning a $5 million Lotto 6/49 Classic prize in the October 9  draw.

Adam said he has a few ideas for his most recent windfall.

“I’d like to look into investing,” he said. “Real estate, stocks, and bonds, that sort of thing. I’m feeling very focused this time around.”

All forms of gambling, including the lottery, involve risk and outcomes are based on chance. Individuals are strongly advised to gamble responsibly. If you are experiencing any signs of gambling-related issues, you can find resources here.

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