Jason Rinaldi – One of Canada’s Luckiest Lottery Winners. A Decade On…

Jason Rinaldi - One of Canada’s Luckiest Lottery Winners

When someone makes a massive win on the lottery people become fascinated not only with their past life but what becomes of them a few years down the line. For some, those tales are not so positive, with stories of losing it all, battling addictions or ill health, or fading into obscurity.

One extremely positive story of a great lottery win doing good for someone is for lucky lottery winner Jason Rinaldi. A decade ago he was one of the biggest single-ticket lottery winners in Canadian Lottery history, scooping a cool tax-free $35.3 million Lotto 6/49 jackpot.

What happened to him? Read on to find out about Jason Rinaldi, one of Canada’s luckiest lottery winners, a decade on.

What would you do if you won millions of dollars on 24Lottos?

Jason’s Lottery Win

Jason Rinaldi

Ten years ago, Rinaldi made headlines when he became one of the biggest single lottery winners in Canadian history. He went from went being a 28-year-old businessman, with a passion on the side for cars, to having $35.3 million in his bank account after an astonishing lottery win.

Often we read about people who win such extraordinary amounts and then go off the rails or fail to cope with the sheer enormity of their win. This, for once, is not one of those stories. Rinaldi has found his win has done nothing but good and with the support of a good family network and some decent friends, he’s not only put his win to good use – but grown his fortune too.

He’s recently donated $500,000 to Ryerson University’s Rams Care camp program. This brilliant scheme is one that will ensure children from deprived neighborhoods in the area will be able to further their education and get mentoring from sports people, at the newly named Rinaldi Family Kids-to-Camp program.

“There’s nothing cooler than seeing a young kid having fun,” Rinaldi said after his donation. He says that winning the lottery was wonderful, but that giving the money away is the thing that has given him the most happiness and contentment.

How Jason Rinaldi Achieved His Huge Jackpot Win

After his win, he initially said all he wanted to do was buy a brand-new Corvette and go to Las Vegas. At the time, his mother said that any woman who wanted to date him would have to be vetted by the ‘pit crew’ that’s to say, all the women in the family.

He even said he’d continue with work. There was the obligatory strangeness that accompanies a lottery win. He said that people discovered where he worked – a Hot Rod Shop and began sending begging letters, not only there, but to his home.
“They would send pictures of their family and a write-up of why they needed money and why I should give it to them. That was the most uncomfortable thing, because you didn’t know if it was a real thing, and you don’t know if it was a scam.” He said. Then, people started showing up at his home. He said they’d “Ask for stuff, it’s not the worst thing to ask for help, but that just freaked me right out. I felt more in danger. That’s why I never went back.”

He decided to quit his business, sell his home and move back to live with his family so that he could feel safe again. He loved spending time with his father, Frank, who he would sit and talk to, to ground him. Frank was the man who instilled a love of cars in Jason and together they learned how to look after and maintain them. Rinaldi studied to be a tradesman at Durham College and figured he’d become a mechanic.

He bought his Corvette but never made the trip to Vegas. Instead, he decided to house hunt, and find somewhere that had a car shop too. Eight weeks later he found a house and 18 acres, which he still owns today. When his father, Frank, died in 2011, his mother and sisters came to live with him there.

Financial Advice

One thing lottery winners are told, but rarely follow up on, is to get sound financial advice from professionals. Rinaldi was sensible enough to do this and got an accountant.
He went from having a bank account to have major investments.

“I don’t do anything crazy,” he says of the money he won.

He admitted he partied a lot and turned the basement of his home into a party space, complete with a bar, outdoor swimming pool, basketball court, and a coach house. He has a movie theatre with a large curved screen and seating for ten guests, a wine cellar with room for well over a thousand bottles, a games room with a billiard table and card table, and an arcade with pinball and video games.

He vacationed in the Caribbean and the Cayman Islands, often taking his Mom with him, and spent money on Raptors season tickets, eventually buying a home in High Park with a cousin. However, he’s since given up the seats and sold the house early in 2018.

He was utterly determined not to be a statistic – or lose all of his money stupidly. “It was a weird feeling of this new-found fame and money. We went to my friend’s bar, and people were coming up to me asking to take pictures and stuff, and it was like, why? What are you going to do with this picture?”

He decided to start giving money to charity, after taking advice from financial professionals.
“It was one of those things I learned kind of quickly. Now I have an obligation, when you have more money, there is that obligation of taking care of others, by your choice,” he says.

The first thing he did was organize a charity golf tournament, with a man called James Barnett. After Rinaldi’s dad passed away, and Barnett had moved on to the University of Ontario Institute of Technology, Rinaldi donated there which resulted in an engineering room being named for his Father, Frank. Barnett then reached out to Rinaldi when sponsorship money was coming in short for a national women’s volleyball tournament two years ago. Rinaldi donated the money that was needed.

Then he gave a $500,000 gift to the Rams Care program. Speaking of his donation, he said: “You hear about young children not having the opportunity to do stuff, but when you see it yourself (and they have the opportunity) it’s like, oh, wow,”

Barnett, of his friend, Rinaldi says: “Over the course of the last 10 years, I think he’s just made it a part of his life to give back to the community. He knows that he’s very fortunate in winning the lottery and I think he’s done well in terms of investments and I think he feels very fortunate there also. He’s all tatted up, so he looks like a unique character, but he’s the friendliest guy in the world, the heart of gold.”

Rediscovered His Love of Cars

Jason Rinaldi with his 1967 Corvette

Jim Rankin, Toronto Star

Over time his love of hot rod cars came back, and he focussed time and energy on his vintage hot rod business. He still has his 2009 Corvette.

He says now that his desire to party has calmed down, and that the basement party room he set up is a lot quieter these days. To keep stress at bay, he has learned Muay Thai and has a training regimen that includes visits to a friend’s gym (he has a fully equipped one at home, but prefers not to work out there) and regularly runs and cycles.

Of the stage in life he is at now, he says “I feel the best I’ve ever felt, mentally and physically. I don’t look the best, but I’m still working on that part,”. He is coy when asked about relationships only saying that he isn’t married, but he travels a lot with his friends and has been to Austria, Germany, Greece, Italy, and to Thailand to see a friend fight in a Muay Thai competition. His only other real indulgence is tattooed and getting inked up.

Rinaldi’s Advice for Anyone Who Wins The Lottery

He says that having money “doesn’t mean s—. You just have to find your happy spot. I’m getting close to it now. It’s taken so long to figure out what makes me happy. I don’t know if I’ll ever be completely happy. I don’t know if anyone can ever really say that. But finally, now, it’s taken 10 years.”

Another piece of wisdom, he’s learned and wants to pass on. Don’t flaunt your wealth, and he doesn’t. “No one likes a douchebag. Just try to be kind, that’s all now. I think that should be everyone’s motto.”

Having read his story, you can’t argue that Rinaldi has been anything else other than kind. It’s sometimes so lovely to read a story of positivity when someone wins a lot of money and uses it to help others and do good.

  1. I knew him as a kid. He was a good guy always. He would give the shirt off his back so someone like him striking the lotto is a good omen. I’m sure he dealt with everyone coming out of the woodwork with every story known to man with excuses of why he should give up some money.


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