12-time Molokai Championships Winner, Oscar Chalupsky.

In 1979, at the age of 15, Oscar Chalupsky made headlines at the Natal 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 49 year-old South African who’s well known for both his on- and off-water antics, has won the 30 nautical mile epic 12 times, notching number 12 yesterday, Sunday, May 20, after spending over three years off the podium of any major race.

“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.”

Not bad for a slightly over middle-age man who’s spent the last several years drinking and playing golf.

“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.”

—Dave Costello