Oscar Chalupsky

Few Paddlers hold a record comparable to that of Oscar Chalupsky. Beginning his canoeing career during his school years, his list of accomplishments include twelve time World Molokai Surfski Champion, multiple winner of the Umkomaas River Marathon and Olympic Canoe Team Captain & participant, representing South Africa in the 1992 Barcelona Olympics.

In 1979, at the age of 15, Chalupsky made headlines at the South African Surf Lifesaving Champs, winning the Junior and Senior Ironman Titles on the same day. In 1983 he won the storied Molokai World Championships open-ocean race for the first time. Since then, the now 51 year-old South African who’s well known for both his on- and off-water antics, had this to say about winning his 12th title at the age of 49.

“I wanted to lose weight,” Chalupsky says in an interview with C&K contributor Joe Glickman, who points out that Oscar was resembling Santa Claus around Christmas time this past year, “and since I’m extremely goal oriented I decided to use Molokai as the carrot to get back in shape.”

According to Chalupsky, he started his Molokai training routine by waking up at 4:15 AM, checking his email and then running 3K to the gym. Then he would head to the sauna and do half an hour of push-ups, sit-ups and dips. To cool down, he says he would swim 1000-1500 meters, then take a 45- minute spin (bike) class and run back home. In the afternoon, he’d do a downwind paddle, or if it were flat, he’d do “a 45-60 minute technique sessions.”

“I’ve always maintained that age is more about motivation than anything else,” Chalupsky says later on in the interview. “I know you’re not supposed to go as fast at 49 as you did when you’re 39, but I feel that I’m capable of going much the same as I did and, in fact, my times on runs I’ve done for 20 years are much the same. The clock doesn’t lie. The stopwatch worries me far more than Father Time.”