Oscar Chalupsky had no idea about the honour that was coming his way.

He had no idea when, as a member of the Joe Glickman Award’s panel, he stopped hearing updates on who may be handed the inaugural trophy.

And he had no idea when his wife Clare told him to put on a nice shirt, even though he was only joining a video call to help Dawid Mocke ‘teach people how to use a zero-degree paddle.’

“I logged on and saw Beth [Glickman, Joe’s wife] and thought, ‘jeez, Beth is learning to paddle with Dawid? I can’t believe that,’” he laughs.

“Then obviously it dawned on me… And I just couldn’t believe it.”

For an athlete as decorated as Chalupsky – a 12-time Molokai to Oahu champion – it speaks volumes about the award, and what it represents, that he already values it as highly as his finest racing victories.

“It’s all very well winning races and things like that,” he says. “But receiving an award from paddlers from around the world – not only South Africa – is very special.”

“It’s one of those things you just don’t expect, which is different from everything I do – you go to races expecting to win.

“This, I was totally unaware. It was a serious surprise and I see it as a serious, serious achievement.

“And honouring one of my best mates – I used to chat to Joe every day – it’s really, really special.”

The decision to name ‘The Big O’ as the inaugural Joe Glickman Award winner needs no explanation, although the panel members did so poignantly when presenting him with the award, which you can watch here.

While he’s one of surfski’s greatest ever athletes, he’s also its most prominent advocate.

Years spent coaching around the world has seen Chalupsky cultivate a passionate following of paddling enthusiasts – each with their own ‘Oscar story’ to share.

The Perfect Boat for any Paddler

Beyond his larger-than-life character and booming personality is a friend to so many within the surfski family.

A value he doesn’t lose sight of.

“I always try to respond to everybody online,” he admits. “That’s my goal in life, always has been.”

“If I can respond to everybody, I can keep in touch with people personally and keep that bond.

“I help people and coach people all the time – it’s in my DNA.

“Even if you don’t want lessons, I’ll give you lessons anyway!” he laughs.

That honest outlook has been at the front of his mind in recent months, amid his own battle with multiple myeloma – or more simply put, bone marrow cancer.

Earlier this month, he underwent a blood transfusion over an arduous three week period.

“It was tough,” Chalupsky admits.

“I actually didn’t put it in my latest update because it’s so shocking, but one of the guys I started the whole journey with got COVID-19 while I was in the isolation ward and he died. I found out a week later.

“It’s terrible, you just don’t realise how real it is.”

Listening to Oscar’s voice over the phone, there’s no hint of the fatigue that comes with his current course of treatment.

With his immune system weakened, coupled with a global pandemic, he’s now confined to his home.

Except for his wife Clare, there’s no human contact.

Even the everyday requirements like food must be delivered to the house to avoid any chance of picking up an infection.

Some days he may feel well enough to go for a walk, away from the paths of people.

But after getting through one and a half kilometres, he’ll sleep for the rest of the day.

They’re harsh realities – but ones that Chalupsky says are crucial to share, for one simple reason.

“It’s better so have people on your side and giving you encouragement,” he explains. “I’ve taken a leaf out of other people’s books that have done it.

“They say, ‘the one thing you must do is explain and tell people what’s happening because there’s so many hidden gems people can share to help you.’

“It’s something everyone should do, everyone wants to help you.

“Don’t hide behind the stigma. At the end of the day, there’s a lot of people out there with cancer and a lot of people in a similar position.

“It’s like paddling in a bubble and not learning the secrets of downwind.”

Outrageously Light, Built to Endure - Meek Warrior

The Big O is as tough as they come.

But he has no hesitations in admitting just how much he’s cherished the support and well wishes of the surfski community, frequently reduced to tears.

“If you’re feeling that emotion, express it,” he beams.

“Don’t try and hide it!”

Even before his own battle, Chalupsky knew how uplifting it can be.

In July of 2014, he travelled to the east coast of America for the Blackburn Challenge, racing in a double ski with Joe Glickman – who at the time was in the midst of his own cancer journey.

They won that race and then basked in the joy of it afterwards.

A year later, Joe had tragically passed away.

“He was just full of life,” Chalupsky reflects.

“He was somebody special.

“You could phone him up any time of the day, he was always there for you.

“But beyond that, he enjoyed the sport for what it is – it’s camaraderie.”

In the same way that Oscar helped Joe in his fight, Joe – and the award that carries his name – is inspiring Oscar.