Oscar Chalupsky, SA’s toughest sportsman, refuses to go quietly

Oscar Chalupsky is a hard bastard.

That much is evident when you read his book – No Retreat, No Surrender – which neatly captures his balls-to-the-wall approach to sport, and to life.

When men his age are generally in their dotage, Chalupsky is still out on the water, still chasing down the youngsters, still fighting the elements. On top of that, he’s fighting cancer. Not unexpectedly, he’s treating the disease like a bitter rival: with disdain and defiance.

Chalupsky is an outlier in every sense. He was a prodigy in and on the water and he was ridiculously versatile, playing rugby and competing in golf as a scratch player.

What’s more, his competitive juices first flowed when he was a boy – 50 years later and he is no less bloody-minded, no less determined to win.


Chalupsky’s story is one well worth telling and Graham Spence, an old-time journalist who was there for many of Chalupsky’s triumphs, among them the famous Molakai Challenge, reprises many of the fascinating facts and details that came to define Chalupsky’s reputation. He was a hard man long before they became synonymous with top-end sport, and he was a serial winner who took no comfort in merely competing. He was obsessive about winning and the book examines this phenomenon and his almost pathological approach to being first.

He ofted paddled against bigger, stronger, younger and faster surf ski racers, but it was mostly his powerful mind that set him apart. He understood the elements better than most, he harnessed the conditions and his willpower was extraordinary. It was a combination that brought him countless triumphs, often against Olympic and world champions, and frequently gave his niche sport a spotlight it ordinarily wouldn’t have enjoyed.

It was hardly a rags to riches story. Whether it was surf life saving, surf skiing, kayaking or water polo, it was a grind on account of the Corinthian nature of these pursuits. There was hardly any money or sponsorships. Many a night Chalupsky slept on a dingy floor or on a mate’s couch.

Somehow, the 1992 Olympian found the time to eke out a living in the business world, founding several companies and, inevitably perhaps, sometimes getting burned along the way. He brought the same hard-nosed attitude to business that he did to sport. It helped him nail down deals, but it also rubbed some up the wrong way. Failure was thus mixed with good fortune, although Chalupsky always found a way to push on, a fighter to the core.

Now based in Portugal, where he helps run an international kayak manufacturing business, he continues to train and compete. He knows no other way.

He’s outlived the six-month prognosis he was given to live and retains his all-or-nothing approach to everything he does.

As he writes, he’s done enough for three lives. When father time does finally catch up, he won’t die wondering.

No Retreat, No Surrender is a book full of heart and heroism.

For me, having grown up distantly admiring this mad sportsman from the coast, finally reading, and understanding, his extraordinary story was a joy.

His book is well worth a read, and not only because it’s a superb narrative. A percentage of the royalties will go to Campaign for Cancer, a patient advocacy organisation.

A hero to the core.