Oscar Chalupsky is still in the race of his life. Given just six months to live in 2019, he uses the same steely determination that made him a champion sportsman to survive and help others.
Bruised, battle-scarred and brave.
That is the inimitable Oscar Chalupsky.
Oh, yes, and arrogant. His detractors will say that if you don’t know who Oscar Chalupsky is, he will tell you.
The world-famous surf ski champion is unmistakable for his competitive cockiness and legendary outsize confidence that irks and inspires.
There is a marvellous video doing the rounds in which Comrades legend Bruce Fordyce ribs Oscar.
“I’m getting sick and tired of everyone praising Oscar Chalupsky!”
A vexed Fordyce tells the camera: “Everybody praising Oscar’s arrogant
attitude. Yes, it is wonderful …but let me tell you one thing…”
Fordyce tells a funny story about how Oscar got it so badly wrong when they paddled the Dusi together one year, and his insistence on going HIS way landed them in the drink in front of the TV cameras.
“So, Oscar isn’t perfect. But he nearly is,” Fordyce says, lauding Oscar’s latest, greatest struggle.
On 1 March 2025, Oscar turned 62 and had survived 1 923 days or five years and three months with aggressive cancer that has taken him to death’s door twice. Although, you wouldn’t think so.
Oscar seems irrepressible everywhere. Social media is awash with pictures of him playing golf, paddling, walking on the beach and posing with famous people. It’s a far cry from October 2024 in a hospital in Portugal where a priest tried to give him the last rites.
Oscar’s brother, Herman, had flown in to be at his dying brother’s bedside. He stood beside Oscar, clad head to foot in a PPE hazmat suit because the mildest infection would have killed his brother.
Herman watched bemused as Oscar sent the priest packing.
“Thanks, padre, I appreciate the prayers, but you’ve got the wrong room.”
Oscar’s remarkable journey since his cancer diagnosis mirrors the story of his life. As a sportsman, he was defined by a fabled single-mindedness that created an aura of invincibility about him.
Now, he is applying the same uncanny sense of purpose to staying alive.
Talk about Oscar is often ridiculously exaggerated.
Talk to Oscar, and he will tell you he just tries hard.
Somewhere between the myth and the man is the truth.
Oscar was a sports prodigy. At 15, he became the first person to win junior and senior Ironman titles on the same day in the most competitive province in the SA Surf Lifesaving Championships. He was the youngest South African to represent his country in lifesaving, and in 1992, he was the SA team captain at the Summer Olympics in Barcelona. The list of sporting trophies is extensive, but it is worth noting another extraordinary triumph. In 1983, he won the Molokai, a gruelling 52 km paddle considered the most challenging sea race of its kind, through big swells. He won 11 times again, including in 2012 when he was 49.
A cancer diagnosis is gutting. Oscar got the news the day before his wife Clare’s 60th birthday. The couple were terrified. Oscar stopped crying after a minute.
“What’s the use of worrying? Seriously, go and try it now. If you are worried about something, go into the bathroom now and sit down and worry for half an hour. See if that helps.”
Oscar was given six months to live in 2019, when doctors said the tumour on his spine was malignant.
Since then, he has applied every waking moment to staving off multiple myeloma, an incurable bone marrow cancer, a quest detailed in an excellent book he published with writer Graham Spence.
No Retreat, No Surrender chronicles his sporting triumphs and his cancer journey, one that has seen his social media profile explode.
Oscar was never a wallflower, but he has hit the speaking circuit since going public with his diagnosis.
His trademark confidence is tempered by a humility that only someone in his predicament can have. Yes, the story is a lot about Oscar, but because he’s so candid and has spectacular access, he’s using the diseases to raise awareness about cancer, treatment and crackpot remedies.
“I have heard it all. People say to wear these shoes, carry this disk, try this, try that and use CBD oil. Everybody is different, and cancer is different for different people, but honestly, most of what is bandied about is bullshit.”
Oscar has stayed alive by refusing point blank to bow to bad news. He transforms a sliver of good news into a ray of sunshine.
“I have my ups and downs. My face is puffing up from steroids. Chemo lowers the immune system. I have sores. I don’t look good. But, if you stay positive, everyone else does. If I am down, it weighs everyone down. My doctors often take my bloods and say, ‘it’s impossible, you shouldn’t be alive.’
“He shows me bad results, and I say: ‘But look—there’s an improvement there’. One percent is an improvement.”
The upshot of all this is that Oscar has created a movement to sustain him. The energy and exposure have generated enormous publicity that calls to mind movies like Being John Malkovich or The Unbearable Weight of Massive Talent starring Nicholas Cage. Only, Oscar doesn’t have existential dread, and he’s entirely comfortable with the bizarre nature of fame.
It facilitates a personal connection with other cancer survivors that boosts his fight and inspires others. Oscar describes himself as a fat boy who blossomed early and did well in sports because of sheer physicality at first. That gave him a taste for success, but he also realised he was more determined than talented.
“I am Mr Average, and I apply myself. Nothing comes easy. I am passionate, and I put in a lot of time. I study technique. I am using everything I have learnt in sports to stay alive.”
This means researching cancer specialists and treatments.
He can do this because quiet, understated Clare is at his side, and friends worldwide are rallying for him and paying for his treatment.
In November 2024, Oscar set up a WhatsApp group announcing that Durban businessman Simon Downes would manage fundraising for his R120 000-a-month-treatment.
“If you don’t have money for my disease, you are dead. That must change. I don’t have to worry about how to pay for my next treatment because I have an incredible team. Not everyone is that lucky.”
Oscar’s survival is down to grit, gratitude, the right medicine, daily exercise (even if modest) and frequent fasting.
“I was on my deathbed, and I told the doctor I was going to fast for 21 days. He said that was ridiculous. I said, ‘This is how I will beat this.’
“Food was interfering with the medicine.”
Oscar hopes his current treatment will give him another six to 18 months. After that, there are other treatment regimes. “I have to make them last. I don’t fear death, but I don’t need a moment’s silence just yet. I can help more people alive than dead. Practice doesn’t make perfect; it makes permanent.”
