Oscar Chalupsky on his way to his 12th Molokai Championships win. Photo: Tom Kerr

By Joe Glickman

For someone who is basically my father’s age to win is mind blowing. It’s one of the best sporting performances I have ever been part of.” —ninth place finisher, Michael Booth, age 21.

Two hours and more than half-way into the world’s most famous surf ski race, 11-time Molokai Champion Oscar Chalupskysat seventh. While he maintained visual contact with five of the six paddlers up front, Aussie Clint Robinson, the defending champ, was out of sight and all but certain to claim his third straight title.

Given his age, the fact that when he’d started training two months earlier he weighed 268 pounds, that his foot was cramping, and, of course, that the paddlers ahead were younger, faster and fitter, the odds that the 49-year-old from Durban would win his 12th title seemed somewhere between No Way and Jose.

Oscar is famous for his downwind prowess—the bigger and more raucous the conditions, the better he rolls—and a level of self-confidence that at times can seem delusional. Behind the bluster, however, are countless hours of training time devoted to technique, and, perhaps most important, a commitment to this race over all others. Molokai is often called the unofficial World Championship of the sport; to Oscar, the man with the most Molokai titles, it is unequivocally the best downwind paddle on the planet.

With 15 miles remaining, the balding redhead slurped a GU, took a pull of Cytomax, shortened his paddle from 215 cm to 213 and had a proper shit fit. “Stop using your arms,” he screamed over the wind. “You have the f#*king strongest body…Drive with your legs…”Nobody has as much power as you. NOBODY!”

Before the GU had time to settle, he surfed by Aussies Michael Booth and Bruce Taylor.

Two down, four to go.

The 2012 Molokai Championships 2nd place finisher, Clint Robinson. Photo: Tom Kerr

Soon after, Marty Kenny, a perennial top-five finisher, spied Oscar approaching. Kenny knew that Oscar aimed to stay in contact with the leaders for the first two and a half hours and then have a proper go. Still, he was impressed by Chalupsky’s sudden acceleration. As he put it, “The Fat Man, who wasn’t fat any more, was flying.”

Kenny followed Chalupsky for 20 minutes until cramps gripped him hard and he fell back. When Oscar passed countryman Matt Bouman, a pre-race favorite who’d punctured profoundly, he was third. Oscar shouted to his escort boat. “Where’s Robinson?”

“Out of sight,” came the discouraging reply. Just ahead, however, was the next step on the podium: nine-time Molo champ Dean Gardiner.

Deano is as chilled about his goals as Chalupsky is intense. But Gardiner, who had started uncharacteristically hard, is Chalupsky’s equal downwind and when properly motivated is just as willing to hurt himself. He knew something that Chalupsky didn’t: Robinson was out of sight because he had dropped back. As the striated cliffs grew ever larger, Gardiner’s elusive 10th title seemed tantalizingly near.

Until Oscar appeared.

Chalupsky made “a definitive pass,” but Gardiner refused to let go. For the next three miles, the longtime friends and rivals diced downwind. Oscar reached the edge of the wall first, five boat lengths up on Gardiner.

The two-mile stretch to the bridge that marks the finish at Hawaii Kai is into the wind. After 32 miles of sprinting for runs, the physical toll is enormous. Oscar was physically at the edge of the ledge but his technique never deserted him. He caught a wave over the reef, clipping his rudder— “Jezz, that was close,” he thought.

Violating his own rule, he glanced back again to check on Gardiner. Dean had mercifully fallen away, but just 200 yards back was Clint Robinson, the former Olympic Gold medalist, closing fast in a shiny black boat of his own design. Oscar leaned into the wind and hammered toward the line. He crossed it 20 seconds ahead of Robinson, who’d been cramping for much of the last two hours.

In the footage of the finish Oscar looks uncharacteristically subdued. In fact he was hyperventilating, physically unable to muster a smile, let alone raise his arms. When he finally caught his breath, his post-race wrap up said it all: “I can’t believe it. It’s my best win ever.”