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 Lewis wins Molokai 2008 (Hank McGregor behind) (Pic: Vince Bechet)
Two hours and forty minutes into the race he covets most, Oscar Chalupsky figured he had his 12th Molokai title in the bag..
Of course, Oscar has rarely met a race he didn't think he could win. In 2006, he felt a tactical blunder in the last few kilometers allowed Clint Pretorius to break through. Last year, he did enough 50km downwind sessions to shred a sail, but on race day the wind vanished, the sun blazed, and the 45-year-old from Durban faded to fourth - his worst finish in 15 tries. "Had there been normal trades," he said, "I'd have won easily." Typical Oscar bluster, but a few weeks later he beat most of the same guys in cranking downwind conditions in Durban, lending credibility to his claim.
 Oscar and Herman Chalupsky mid channel Molokai 2008 (Pic: Vince Bechet)
Let me get this out there straight away: I'm an Oscar fan. The guys who enjoy Oscar (GWEO) take his non-stop, over-the-top pronouncements on the uselessness of every other ski in the world compared to his Epic, the futility of OC1's, the stupidity of including the Cape Point Challenge on World Cup, and anything else ticking him off at the moment with multiple grains of salt and focus instead on his endlessly optimistic attitude, his willingness to help newcomers in Hawaii (even an Australian in a Fenn) and his infectious desire to train hard and drink harder. But no matter which side of the Big O fence you stand on, it's next to impossible to ignore that over the last three decades no one has done more to turn this 55km crossing into the ski race every great paddler wants to win.
Unless maybe it's Dean Gardiner: Courageous and supremely skillful one race, completely disinterested the next -- and largely mum about his training or tactics in between -- the laid-back, charismatic former commercial fisherman that I know as "the Fish Monger" is considered by many to be the best downwind paddler on the planet; a claim Oscar finds as palatable as non-alcoholic beer. Certainly, he is the face of the race in Australia. Oscar and Dean have won 20 Molokai titles between them. Their duel in 2003 to be the first to 10 Molo wins was a classic, with Oscar catching Deano along the cliffs in the last few kilometers. Regardless, the long-time friends and rivals are the primary reason why each May so many great, near-great and wish-they-weren't-so-average paddlers come to Hawaii to see what all of this "roughest navigable channel" hype is all about.
 Dean Gardiner (Pic: Vince Bechet)
Although there were more world-class paddlers on hand than in any other year, the general consensus was that only six men in the field of 133 had a legit shot to win: Three greybeards -- Oscar, Herman and Deano - and three young Turks -- Hank McGregor, Dawid Mocke and Tim Jacobs. Though the greybeards may have been the sentimental favorites, most expected Hank and Dawid to duel for first with Jacobs standing on the final step on the podium. A flat channel, most agreed, favored TJ. Oddly, no one I spoke to had defending champ Lewis Laughlin in their top half dozen.
The trades had been blowing for weeks when I arrived 10 days before the race. For my first paddle I headed from Hawaii Kai out to the wall along Portlock Point. After months of training in an Olympic K1 on a frigid bay, it was a thrill to get out on the water without pogies, spray skirt, or wool hat, with the sound of the wind and swell rebounding off the rocks, the inviting turquoise water infused with frothy white spray, and -- 20 minutes into my downwind jaunt to the Outrigger Club in Waikiki -- a dolphin escort. The runs were big enough to scare the chill out of a New Yorkers under rods but manageable enough to be fun.
 Katie Pocock in the Kaiwi Channel (Pic: Vince Bechet)
Further up the coast, Oscar, Herman, Zsolt Szadovszki and Katie Pocock, the women's leader on the World Series Rankings, launched from Makai Pier opposite Rabbit Island. Two kilometers off shore, Zsolt got cleaned off his ski by a wave three-stories high. "It was a monster," he told me later, his eyes as wide as an owl in need of Visine. He was half amused and totally in awe. Even Herman, someone not prone to exaggeration, said he dropped down the face of a run so steep he feared his ski would disintegrate. While such conditions send me shopping for adult diapers, Oscar's mantra all week was: Blow, baby, blow!
But as the week wore on, the forecast on WindGURU called for light and variable winds on race day, and even Oscar's unbridled optimism took a hit. The wind, or lack of it, became the topic on everyone's mind: How much? How little? What if it dies? What if I die? And everyone, it seemed, had their own best case scenario. Molo rookies wanted it big but not too big; Cape Town's Peter Cole would have signed on for rain, wind and cold. Tim Jacobs, fresh from his win at the King of the Harbor win in New Zealand, said a head wind suited him just fine. Dave Kissane, who had just resumed training after a shoulder injury, had done no long sessions and prayed for the wind to blow. Marty Kenny had trained diligently but felt that in order to crack the top five he needed the channel to stand on its head.
At first light on Sunday morning the rustling in the palm trees lifted the spirits of the largest surf ski field in race history. After one false start, the game was on. Kissane, who went out conservatively, described the start this way: "After 1km I was in disbelief at the pace of the frontrunners. I began to settle into a nice pace with my mate Dean Beament. We speculated that some of the guys were going to pay a very painful price for forgetting this was going to be a four-hour slog in hot, relatively calm conditions."
The leaders formed four distinct lines: Furthest south - just above the rhumb line - was Oscar, Marty Kenny and, an hour into the race, Herman. Roughly 750 meters north were Tim Jacobs, Damian Daley and Szolt. To their right, Hank McGregor; and higher still, Dawid Mocke. Dean had started with Tim Jacobs, but was dropped early on. What Tim didn't know was that Dean had moved to the south and joined Lewis, north of the Chalupskys.
 Race positions courtesy of www.sportstrack.net
For a larger image click here.
GPS Analysis - the red line shows Oscar Chalupsky's track in the 2006 race (which had classic downwind conditions)
For the first two hours, the runs, though small by channel standards, were there. But as the third hour neared, the wind died, the tide turned and the heat intensified; scratching onto the bumps became exponentially harder. As Marty Kenny said: "The conditions were deceptive; just enough swell to tempt you out of your comfort zone with less reward than expected." With roughly 10K to Portlock Point, the end of the wall that marks the last downwind section of the race, boats were so spread out that no one up front knew where they stood on the leader board. Oscar's escort boat driver, Marshall Rosa, zoomed north in his twin-engine 500 HP skiff to check on the competition. A native Hawaiian who finished second to Oscar six times during the 1980s, Rosa knows the channel as well as anyone. Minutes later he reported back that that Team Chalupsky was slightly ahead of McGregor, Jacobs and Gardiner. Mocke, he said, was way north and out of contention. "You're on the right line," he shouted. "Stay strong and you've got it!"
Instead, Oscar punctured so badly that had he been driving tire shreds would have been scattered across the highway. Oscar had been struggling with the hose in his drinking system all day and was probably under-hydrated. But Herman had drained nearly three liters, and he imploded soon after as well.
Similar melt-downs were occurring all across the channel. Zsolt Szadovszki, who'd moved from San Francisco to Hawaii four months before the race "to figure this surfing stuff out," was fit and flying come race day, but after 90 minutes of shadowing Tim Jacobs, he cramped so badly he could no longer lift his stick. Last year, his first Molo, he finished sixth just behind Clint Pretorius; this year he wouldn't finish. For the first two-and-a-half hours, Barry Lewin, a lanky 24-year-old from Durban, was sitting solidly in the top 10. But before you could read his latest post on http://www.barrylewin.co.za/, he became dizzy and disoriented. He limped home in 21st - in his words, a humbled, broken man. Ian Gray, one of Lewin's house mates in Hawaii, had logged nearly 600 downwind kilometers since arriving in Oahu at the end of March. Though he looked as fit as a Stradivarius, around the third hour he lost his breakfast and began seeing stars - not a good sign at 11 AM. "It became a survival game to get to the finish," he wrote. "Those last 10km were tortuous."
In my six trips across the channel, I've seen it big and booming and I've seen it hot, flat and cruel. This year it was both. If the race was purely a physical challenge, the fastest, fittest guys would win, but managing the course is a huge part of the equation. Just ask Nathan Baggaley or Clint Robinson -- or Dawid Mocke. Last year, Mocke hung with the front bunch for two hours before making his break. Though he led late in the race, he hung too far south and bogged down in the fierce current wrapping around Oahu; Lewis Laughlin and Hank McGregor found faster water and finished 1 & 2.
This year the 30-year-old from Cape Town planned to paddle his own line up north rather than cover the front runners. In the first hour he figured that he was running a competitive second to McGregor. Around hour two he pulled even with Hank who was 500 meters to his left. Had the wind continued to blow, Mocke's line might have paid dividends. But the opposite occurred. Slowly, imperceptivity, the wind died and the two-knot current pushed him further north. With 10km to go he spied a handful of escort boats up ahead and realized he'd made a serious tactical blunder. "It took a fair amount of determination to consolidate my efforts," he said. "Had I just given up at this point I could very easily have been outside the top 10."
With Oscar and Herman undone and Mocke out of the picture, the 32nd edition of the Molokai Challenge became a four-horse race. For my rand, Hank McGregor, the 30-year-old from Durban, seemed the most likely to break through, especially considering his string of close second-place finishes in '07: at Molokai (Laughlin), World Cup Durban (Chalupsky) and Dubai (Mocke). This year the former World Marathon Champ blasted off the line, opening a 250 meter gap 30 minutes into the race. Off on his own for nearly three hours, Hank followed the small black arrow on his GPS like a blood hound would a scent. Periodically the press boat came by and let him know that he was leading the mob up north. Only when he neared Portlock Point did he realize that Gardiner, Jacobs and Laughlin had slipped by on his left.
 Hank McGregor passing Portlock Point (Pic: Vince Bechet)
Of all the paddlers left standing, the most surprising was Gardiner. The 43-year-old father of newborn twins, Dean arrived in Hawaii two days before the race, doling out insults, nicknames and good cheer in equal measure. Two hours into the race the conditions were so subdued, so un-Dean like, that Dave Kelynack, on Jacobs' escort boat, wondered out loud if Dean was still in the race. (After all, last year, Dean noted the lack of wind, wished us good luck, swam out to his escort boat and was drunk by 10am.) But then Kelynack spotted a paddler in a red vest with his head cocked to the side going flat out. Incredibly, Dean caught and passed Tim. "I'd never seen Deano so strong in my life," Kelynack said, clearly impressed. Citing the fact that Dean had been quietly training hard in the flat water, he added: "I think he wanted his 10th title quite bad."
 Dean Gardiner in mid-channel (Pic: Vince Bechet)
As Oahu loomed large three hours into the race, Laughlin, Gardiner, and TJ had a slim lead on Hank, who had dropped down to met them along the cliffs. Though he'd been paddling with Dean much of the race, Laughlin only realized he was in the hunt when the press helicopter buzzed overhead to monitor the leaders. "Being that far into the race," he said, "my only preoccupation was to save energy and keep up with my speed."
 Tim Jacobs (Pic: Vince Bechet)
The 39-year-old Laughlin, who'd done heaps of three-hour paddles in the stifling heat of Tahiti in the month leading up to Molokai, rounded Portlock Point first, followed by Dean, Hank and TJ. McGregor and Jacobs, who have logged countless hours in Olympic kayaks, dispatched Deano over the last two kilometers. But Laughlin was too strong and the gap too big. The taciturn father of five, who'd been largely left out of the conversation as a potential winner, prevailed for the second consecutive year, becoming only the fifth man with two or more Molokai wins on his resume. Hank was 30 seconds back with Jacobs and Gardiner in third and fourth, Mocke fifth.
 Lewis 'seemingly unaffected by the heat' (Pic: Vince Bechet)
Strong and seemingly unaffected in the heat, Lewis was as steady all day as the channel was changeable. Though he skipped the award's banquet, in an e-mail to Rob Mousley he wrote: "Being successful at Molokai this year doesn't mean that I have beaten anybody, like many wanted me to say. To me the South Africans and the Australians are the best ocean paddlers in the world. I just tried to keep up the best I could and make my way across the channel. I had no tactics or special course whatsoever. I just tried to give my max out there. I felt blessed for having a good one."
I myself had a shocker. Halfway across, I felt so lethargic that I stopped caring. Then along China Wall, I got slammed by a breaking wave paddling across the reef, sheered the rudder completely off the ski -- suffering a tidy bit of reef rash in the process -- and paddled back to the finish so slowly you could have used a sun dial to monitor my progress.
To add insult to injury, I had to catch the red-eye to New York that night. I was waiting outside the Park Shore for a cab when Oscar offered me a lift to the airport. Oscar's seventh-place finish was his worst ever. In between telling me what a stunning goofball I was for paddling over the reef, he struggled to figure out why he'd fallen apart so spectacularly despite having paddled conservatively over the first half of the race. Just before I hoisted my battered body out of the car, Oscar said that he hoped the guys back home would now realize how difficult it is to win Molokai. I suppose Oscar hoped I would say as much in print, but Dawid Mocke summed it up so well that I'll give him the last word:
"When I realized I had messed up it up," he e-mailed me in response to my request for his impressions of the race, "it dawned on me that this truly is a great race. It's everything but straightforward. Being super fit doesn't guarantee you a victory since so much more needs to come together on the day. It's almost as if the Channel decides who deserves to win."
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on a fantastic article! 
You have a wonderful artistry of the written word not only a great report on a great race but very enjoyable to read
Cheers
Tom.B