"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."
This video clip, made by Dolan Eversole, has some superb shots of Dean and Oscar dicing along China Walls. Oscar is in the yellow shirt, closer to the rocks; Dean is in the white shirt on the ski with a blue deck.
Next on the clip, you can see Clint Robinson on the red-decked ski, followed by Dean Mercer on a white ski.
Trans World Sport
In 2007, Trans World Sport, made a short video about Oscar Chalupsky.