Oscar Chalupsky

Oscar Chalupsky is one of the most-decorated and recognised water-sportsmen in the world. His resumé spans over an incredible 45 years, with few paddlers holding a record comparable to this. His effortless technique and knowledge of the ocean have seen him achieve results some athletes can only dream of including 12-time Molokai Ocean Ski Champion, multiple winner of the Umkomaas River Marathon and Olympic representative.

What’s outstanding about Oscar is his longevity and tenacity which has seen him take on and beat athletes over 30 years his junior. In 2012, at 49 years of age, Oscar took home his 12th Molokai title, 29 years after his maiden win. A truly inspiring result.

On top of his ocean ski successes, Oscar competed at the 1992 Barcelona Olympic Games where he was the team captain for South Africa. He is also a multiple winner of the prestigious Umkomaas River Marathon.

Oscar won the world-famous Sella Descent in Spain in 1986 with his brother Herman. The biggest marathon race that everybody wants to win. His father won the same race in 1968 and both their names are carved into the bridge over the Sella River. Oscar came second in 1981 with Matt Carlisle. With his brother Herman, they had five top 3 finishes.

The above already would take a ‘normal’ elite athlete several lifetimes, but Oscar also won the 240 km Port Elizabeth to East London Challenge, 10 times. This endurance feat started as a friendly challenge on January 7, 1972, between ultra-distance runner John Ball and Surf Lifesaving legend John Woods, who would paddle the race, where the outcome would indicate who was faster – the runner or the paddler? The Challenge is the ultimate contest between man and the elements of nature, a reputation that has enticed competitors back every time it has been staged.

Away from the competition arena, Oscar has played a vital role in the development and success of Ocean Ski Paddling. In 2000 Oscar co-founded Epic Kayaks, which today is one of the leading brands in Open Ocean Ski Paddling.

Oscar’s many successes have inspired the paddlesports world and left people wondering how he does it. In a bid to answer these questions, Oscar conducts surf ski clinics around the world which teach paddlers how to train, race and win using his methods and technique. With thousands of people already beneficiaries of Oscar’s expertise, he has left an everlasting impression on this community.

Oscar Chalupsky is larger than life, a legend to some and known for his particular sense of humour; the way he is able to light up a room with his energy and passion. Oscar’s service to the paddlesports community has already spanned over 45 years and lucky for us, there are no signs of him slowing down.

Further achievements:

  • 1st person in the world to win Junior and Senior Iron Man champion, South Africa – on the same day
  • Multiple Surf Lifesaving awards
  • Multiple winner of open ocean surfski races in Tahiti, Australia, Hong Kong, Caribbean, USA, Spain, Sweden and Denmark
  • Notable golfer, reduced 24 handicap to a scratch within a year.
  • a ‘Sportsman of the Decade’ nominee
  • nominated as one of the 100 most influential persons in South Africa