The practical reality of being an Olympic athlete is that few get to practice their sport full-time forever. Unless you’re a household name like Usain Bolt or Michael Phelps, almost all Olympians have to take on a day job while training and competing. And after retiring from a sport, athletes usually transition to a different career.
Canada’s Olympic athletes have included successful businesspeople, firefighters, engineers. Other Olympians have taken more surprising career paths — including an OnlyFans star and an internationally wanted drug lord.
Here are five Canadians whose career trajectories took some unconventional turns before, during, and after their runs as Olympic athletes.
Alysha Newman: OnlyFans pole (vaulting) star
Alysha Newman’s side job as an OnlyFans star brings her more income than her career as an Olympian probably ever will.
The athletic beauty won bronze at the Paris 2024 Summer Olympics, making her the first Canadian to win an Olympic medal in pole vaulting. Her prize was a $10,000 CAD award from the Canadian Olympic Committee’s Athlete Excellence Fund. But when you add up the cost of coaching, medical expenses, training, equipment, travel, and cost of living, that money covers a lot less than you’d think.
Luckily, Newman’s earnings are much more lucrative on OnlyFans. On it, subscribers pay $12.99 USD a month to see revealing images of Newman’s bikini-clad six-pack.
The Olympic athlete has been on OnlyFans since before 2020. By her own count, in 2024 she had over 30,000 subscribers and it was only growing. Her subscriber count exploded after her bronze win in Paris — which she celebrated with a viral twerk to the crowd — so much so that it actually caused her OnlyFans page to crash.
In an interview with the CBC, Newman said that she “started seeing a revenue I had never seen” after being on the platform. OnlyFans creators keep 80% of their subscriber fees, so a rough estimate would put her monthly revenue at $228,560 USD a month (assuming 10,000 subscribers at $12.99 and 20,000 subscribers at the promotional price of $7.79 that Newman set it down to during the 2024 Olympics).
Newman has invested that money into crypto and AirBnB properties, as well as preparing for the 2028 Los Angeles Summer Olympics. According to the Daily Mail, she has installed a home sauna and hyperbaric chamber, and has regular medical tests and chiropractor treatments to keep her in tip-top shape.
Newman isn’t fazed by the stigma around being an OnlyFans creator: “I can be an Olympic medalist and still embrace beauty, style and femininity. That balance is where my confidence comes from.”
Amateur athletes are traditionally underfunded in Canada. Despite this, Newman has trained hard for her body and her athletic prowess. If she can monetize her fans’ appreciation of these to achieve her best and secure her finances — then more power to her.
Ryan Wedding: snowboarder turned narcotics kingpin
Ryan Wedding was the head of a violent drug empire with a reputation as a “modern-day El Chapo”. He had been on the FBI’s Top 10 Most Wanted list with a $15 million USD bounty on his head before being caught in January 22, 2026, after ten years on the run.
He’s also a former Olympic snowboarder and Canadian national snowboarding champion.
Wedding grew up in a family of competitive skiers. Competing internationally from the age of 16, Wedding won silver and bronze titles in the Junior World Championships in snowboarding. Three years later, he made Canada’s Olympic team for the 2002 Salt Lake City Olympics. Ross Rebagliati, an Olympic snowboarding gold medallist with a controversial career himself, met Wedding at the time. He recalls that he was “probably gonna be hard to beat.”
But that was where Wedding’s Olympic career started and ended. He failed to qualify for the Parallel Giant Slalom event, where only the fastest 16 competitors advanced.
His Olympic ambitions were never achieved, but Wedding wasn’t going to settle for an ordinary existence. His criminal career started with an illegal marijuana grow-op in British Columbia before he got busted trying to buy 24 kg of cocaine from a U.S. government agent in 2008.
The crimes only got more serious and brutal from there. Wedding ran an international drug smuggling operation spanning Mexico, the U.S. and Canada, bringing in billions of illicit dollars. He was ruthless about eliminating people in his way. He allegedly ordered the murders of trafficking rivals and witnesses, including a Toronto couple who were tragically gunned down in a case of mistaken identity.
And yet maybe things would have turned out differently if Wedding’s Olympic career hadn’t ended prematurely.
When the FBI raided his possessions not long before he was captured, they found two Canadian snowboarding medals amongst $40 million dollars’ worth of luxury cars and motorcycles. Which suggests that, after more than two decades, Wedding still had sentimental attachment to his achievements as an erstwhile elite snowboarder.
A former snowboarding teammate of Wedding pointed to the counterfactual possibility: “Had we maybe done a better job of harnessing his energy, his ability to think and create and strategize, maybe Ryan could have been doing something really special for the country instead of hurting people.”
Ross Rebagliati: Olympic gold medallist and cannabis entrepreneur
Ross Rebagliati’s Olympic victory in the first-ever Giant Slalom event at the 1998 Nagano Olympics was what ultimately led him to open up a marijuana company.
To be precise, it was while the Canadian snowboarder was being held in a Japanese prison cell for 11 hours for alleged drug smuggling that he decided to “fight about this plant for the rest of my life”.
Rebagliati reached the top of the Olympic podium in Nagano, but it was a short-lived celebration. A drug test he had submitted contained traces of THC (marijuana) and he was stripped of his gold medal, despite THC not being on the list of substances banned at the Olympics at the time.
The Canadian Olympic Committee appealed the decision, and Rebagliati himself claimed that the trace amounts came from second-hand smoke rather than direct consumption. (He admitted later to having last used it in 1997.) Rebagliati got his medal back.
But the damage was done, and Rebagliati never competed at an elite level again. He worked in construction for the next ten years, making barely enough money to afford car insurance. After the September 11 attacks more than ten years later, Rebagliati was included on the U.S. no-fly list due to his documented use of cannabis. Even today, he is unable to enter the U.S. without a waiver.
After 1998, THC was named a banned substance by the World Anti-Doping Agency. This probably fueled Rebagliati’s conviction to be a cannabis activist. In 2013, he opened up his own cannabis company called Ross’ Gold, selling medical marijuana strains with names like “Ross’ Platinum”, “Ross’ Gold”, “Ross’ Silver”, and “Ross’ Bronze”.
When Michael Phelps got caught smoking marijuana, the media reached out to Rebagliati for a quote: “it’s calorie-free, fat-free, no hangover”, was his defence.
Rebagliati has become a passionate advocate for the medical and analgesic effects of cannabis. “Having been part of a stereotype that was demonized, I feel like it was my responsibility to shed light on cannabis”, he explained in an interview with Yahoo! Sports.
In 2018, cannabis was legalized for non-medical use in Canada. It took two decades, but Rebagliati was vindicated in the end.
Deanna Stellato-Dudek: the cosmetologist who came out of a 16-year figure skating retirement
Ten years ago, American-born Deanna Stellato-Dudek was the director of aesthetics at a plastic surgery clinic. In a couple weeks, at 42 years old, she’s set to compete for Canada as the oldest Olympics figure skater in over a century.
Stellato-Dudek’s career path is as full of twists and turns as any of the Olympians on this list. As a teenager, she had a promising career in singles skating, winning the 1999/2000 Junior Grand Prix Final and silver at the 2000 World Junior Championships. She had dreams of competing for the U.S. in the 2002 Salt Lake City Olympics.
But then a series of injuries forced her into retirement. For the next 16 years, the former figure skater worked for a plastic surgeon in Chicago leading a team performing Botox, laser resurfacing, and other non-surgical cosmetic procedures. She got married and had kids.
Then a chance conversation over lunch got her thinking, what if she could try for the Olympics again? At 32 years old, the aesthetician relaunched a career in pairs skating. She quickly won bronze medals at the 2018 and 2019 U.S. Championships before her skating partner’s injury forced her to look for a new pairs partner, which she found in Québecois Maxime Deschamps. (At her level, there were no other men suitable in the U.S.)
Let’s place the unlikeliness of Stellato-Dudek’s career reboot in context. Figure skating is a young girl’s game. Out of the last eight Winter Olympics, only one of the gold medallists in women’s figure skating has been over the age of 19. The extreme technicality of maneuvers like “quad revolutions” is easier for younger, lighter girls to perform.
Pairs skating is even more dangerous, with jumps, lifts and throws that require the pair to be in perfect synchronicity. Stellato-Dudek has said she spends three hours recovering each evening, something which probably correlates with age.
Then there were the practical obstacles. The former aesthetician had to rely mostly on her savings to train, including money from an online business she sold to her former bosses. Up until 2024, as an American she wasn’t eligible to receive funding from the Canadian government.
Nor do the Olympics allow for mixed-country teams. In order to compete with Deschamps for Team Canada in 2026, she had to get Canadian citizenship first, and there is no fast-track for aspiring Olympians. She received her citizenship just in time, in December 2024.
Despite all odds, Stellato-Dudek and Deschamps have gone on to have a stellar run. They’ve won multiple Grand Prix, gold at the Four Continents Championships in 2024 and silver in 2025.
They’re set to make their Olympic debut in 2026, but a late-breaking twist might derail Stellato-Dudek’s story again. Just four days before the start of the Milan Cortina Olympics, she sustained an injury that forced the pair to withdraw from the team figure skating event. It’s still to be seen whether she’ll be medically cleared to compete in the pair skating event. But her career has the makings of a feel-good movie, and I’ll be crossing my fingers for it to have a feel-good ending.
Yohan Eskrick-Parkinson: the elite diver working two jobs to compete in bobsledding
Yohan Eskrick-Parkinson had only been bobsledding for 1.5 years before he was named to Canada’s Olympic bobsleigh team for 2026. But he had his start in a completely different sport, competing as a diver at an international level from 2017 to 2024.
In one way, his shift to bobsleigh isn’t unusual. The sport often recruits from other disciplines. What makes it unusual is that recruits tend to come from sports that require power and speed, like track and field or football and rugby.
Diving is characterized more by its elegance and technical precision. As a synchronized diver, Eskrick-Parkinson had to focus on executing clean lines and perfectly timed movements, all while looking pretty in the air. In bobsleigh, it’s all about pushing off with explosive velocity.
Eskrick-Parkinson’s entry into bobsleigh happened because of a chance recommendation.
In 2024, his career path seemed clear. Having failed to qualify for the Summer Olympics in Paris, he announced his retirement from diving that year. After finishing his bachelor’s degree in neuroscience from Northwestern University, he was preparing to apply for medical school.
Then he met Lascelles Brown. Brown was a silver and bronze medallist for the Canadian bobsled team in Turin 2006 and Vancouver 2010. He suggested that Eskrick-Parkinson try out bobsleigh.
From there, Eskrick-Parkinson’s bobsled career took off like a spinning dart. In July 2024, he began at a provincial camp before moving on to the national team camp. He slid down a full track for the first time in October 2024. By November, he had already won events at the North American Cup. In late January 2026, he was told he was going to the Olympics in Milano Cortina.
It’s clear that for Eskrick-Parkinson, bobsledding is his chance to compete in the Olympics where he was unable to as a diver. This ambition is what has driven him to go from being at the top of his discipline to being a novice in a completely different one.
It’s not been a fairy-tale transition though. Like so many of the other athletes on this list, a lack of funding has meant that he works multiple jobs to finance his Olympic dream. As well as being a diver-cum-bobsledder, Eskrick-Parkinson can add lifeguard and photography and video editor to his resumé. And maybe, after Milana Cortina 2026, he’ll be able to add “Olympic medallist” too.
