Heading into the final leg of a 34-mile relay race in the waters of Kauai, Australian Rod Taylor overtook the third-place boat and handed me a lead. “Bring it home, mate!” he shouted as I raced off. The wind was howling; the swell, frighteningly big-at least for a flatwater paddler just off the plane from Brooklyn. I hadn’t planned on doing the race-I was in Hawaii for the World Surf Ski Championship, still a week away-but my semi-deranged friend Oscar Chalupsky, South Africa’s most decorated surf ski paddler, felt it would be criminal to miss this warm-up event hosted, as it was, by a beer company.

With the finish in sight, I fixed my attention on a one-man outrigger just ahead of me, making sure I stayed outside the jagged line of breakers. I saw him veer sharply seaward, a move I didn’t quite understand until a 12-foot wall of water reared up and crashed on my head, nearly cracking my ski in half. When I finally limped across the line, Chalupsky and his brother Herman, the winners, were sipping their second Steinlager. Not only did my team finish out of the money, but I would have to pay for the damage to the borrowed boat.

Back on Oahu, I spent the next four days prepping with Chalupsky and a handful of racers. We headed out of the bay on Oahu’s southeast coast where the race finishes to a sheer cliff known as Chinaman’s Wall. Here, after rolling unimpeded for thousands of miles, the swell surges up and slides down the rock face, colliding against the next wave. On a calm day, it’s a challenging place to paddle a sleek surf ski; when it’s rough, you need to duct-tape your cap to your head. Each day I struggled to find a rhythm and tried to feel unconcerned when the South Africans left me far behind. I told myself I’d be fine; after all, this was the most challenging section of the entire course. But the day before we flew to Molokai for the race, we passed a team of divers and a helicopter hovering overhead, searching for a surfer who’d been swept out to sea and drowned. After one broken ski, a week of disjointed paddling, and a fatality, I had about as much confidence as Charlie Brown on the mound.

The element of danger is part of the Molokai mystique. Now in its 29th year, the 32-mile open ocean marathon across the Kaiwi Channel, often called “the roughest navigable channel in the world,” is recognized as the world championship of ocean kayaking. While there are plenty of world-class ocean races-some with larger and deeper fields-no other ski race in the world has such history or prestige, or follows such a challenging course. Typically, the channel runs 4 to 10 feet, with small-craft warnings prevailing. As the race Web site says: “Paddlers must deal with choppy, confused water from the start, where waves and currents from both sides of Molokai converge. The troughs between the waves are deep. Roaring, breaking swells, anywhere from 5 to 15 feet, run down from the northeast.”

In my first attempt at the channel, in 2003, the swell was 10 to 12 feet. (In Hawaii, waves are measured from the back, so if you’re from the mainland, double that height.) While the size and speed of the swell was intimidating, it was the erratic wave patterns and randomly breaking surf that really messed me up.

In 2002, Grant Kenny, a five-time Molokai winner, was flying down the 30-foot face of a swell at 20 miles per hour. He pitch-poled after burying the front of his 19-foot ski into the back of the wave in front of him. He carried on and finished third. Kenny, a two-time Olympian and famed Ocean Ironman from Australia, was the first big name to put his stamp on Molokai, winning his first title in 1979. In 1983, 20-year-old Oscar Chalupsky started a seven-year winning streak. When South African athletes were banned from international competition, Chalupsky was forced to sit out for five years. In stepped Dean Gardiner, the affable commercial fisherman turned boat skipper from Sydney. Gardiner set the course record of 3 hours and 21 minutes in 1997. By 2002, both he and Chalupsky had notched nine wins.

In 2003, the two faced off to see who would be the first paddler to reach 10. For much of the race, Chalupsky labored a distant third behind Gardiner and Aussie Clint Robinson, the 1992 Olympic K-1 1,000-meter gold medalist. Relying on what he calls BMT (big match temperament), Chalupsky dug deep and caught Robinson late in the race. Twenty minutes later, Chalupsky edged next to Gardiner along Chinaman’s Wall. In his nine previous wins, Gardiner had never been caught from behind. In his nine victories, Chalupsky had never trailed with the finish so near. The rivals traded leads, each sprinting for the next best wave in the raucous water along the wall. Gardiner cracked and Oscar captured his record 10th title. Gardiner, Robinson, Herman Chalupsky, and Kenny-a veritable who’s who of Molokai Men-were second through fifth, respectively.

In 2004 many of the heavy hitters were back. While Chalupsky battled a frenetic work schedule and burgeoning waistline, his younger brother Herman, 30 pounds lighter and infinitely less bombastic, was drilling virtually every big surf ski race he entered.

When paddlers began to stir on race day, May 16, 2004, the swell was running from right to left at three to six feet-virtually side-on-conditions that favored the Chalupsky brothers. Both came of age in the rough Indian Ocean and have done scores of brutally long ocean marathons in conditions ranging from bad to horrendous. Headwind, side wind, tailwind, you name it, they’ll go hard. “The South Africans are just a different breed,” Gardiner said before the race. “They’re definitely tougher than we are. They seem to enjoy beating their heads against the wall.”

Gardiner, on the other hand, disdains paddling into the wind and, with a gimpy right shoulder, often falls apart in the side chop. That said, put him in a running sea and he has few peers. After decades of working on boats and countless hours of paddling along the headlands of Sydney, he has an uncanny ability to find, connect, and milk bumps that even world-class kayakers cannot see.

When the gun sounded, Gardiner and Herman blasted off and for nearly two hours dueled side by side, close enough to pick each other’s pocket. Bob Twogood, Herman’s escort boat skipper, was amazed. “They had the entire ocean in front of them and they were still almost banging into each other the whole way,” he said.

“We were battling for the same wave,” Gardiner said later. “It was an awesome race!”