Oddly, the best boat wasn’t the fastest, longest, sleekest sea kayak. In the name of fairness, these faster boats were held back at the start line, allowing smaller, slower boats a head start. There were more than a dozen staggered starts that grouped boats according to their make and model.

As the years went by, race organizers had ranked literally hundreds of boats in this staggered starting line-up, akin to a sort of boat handicapping system. Along the line, some boats were inevitably put in a category they didn’t belong, giving certain boats more of a head start than they deserved. The great scramble was figuring out which boats these were.

“Some people would spend the whole year trying to figure out which boat could bend the handicap rules. It was an all-consuming process around here,” said Chris Hipgrave, a Swain County paddler and Olympic director for United States Canoe and Kayak.

“For years, the whole game was trying to get a ‘cheater’ boat as we called it,” said Billy Richards, a regular competitor in the Tsali Triathlon. “You tried to figure out a boat that was mis-handicapped.”

That meant taking boats out for a test paddle and deciding whether the advantage of a head start outweighed the disadvantages of the boat’s slower design.

“Living around here, there are hundreds of paddlers just in Swain County. I myself have a fleet of 11 racing boats on my deck and each one is different,” Hipgrave said. “So it is not hard to track down the boats that beat the system.”

The longer a boat, the faster it is. Shorter boats got a head start over longer ones. Richards recalls one competitor with fiberglass know-how who sawed off the ends of a $2,000 sea kayak to shorten it — shoehorning it into a category for shorter boats with more of a head start, even though it had the design advantages of a longer boat.

“You could show up and beg and plead and get your boat into a better category and start way ahead of the other folks,” Richards said. “The race wasn’t how fast you were. It was calculating and messing with the boat handicaps.”

This obsession with beating the system may seem extreme, but the Tsali triathlon is considered a trophy event among outdoor athletes.

“If you do well at the Tsali Triathlon, around here you get bragging rights the rest of the year,” Hipgrave said.

Complaints over the system mounted more and more each year.

“Back when the old system was done, there weren’t a thousand boats out there,” Hipgrave said. “The more boats you get into the market place, the more blurred the lines got. The old format was very, very well done, but it was dated.”

Richards was one of numerous paddlers who became disenchanted with the race after seeing the better paddlers get beat year after year due to handicap finagling. The turning point for Richards came two years ago as he watched a U.S. paddling team member compete in the paddling leg.

“Her boat was so poorly handicapped she finished in the middle of the pack with folks who weren’t anywhere in her league,” Richards said.

That same year, Richards watched as a first-time racer who showed up with a super fast 18-foot sea kayak was held back at the start line for so long that the other paddlers were nearly out of sight by the time he took off.

“You could just see him shrinking and shrinking,” Richards recalled.

Enter Hipgrave, who achieved hero status to paddlers like Richards when he volunteered to revamp the system, something that became a personal hobby for him over the course of the next year.

“We started off by establishing what we wanted to achieve, which number one was removing the grumbling for athletes who couldn’t get access to the handicap-bending boats,” Hipgrave said.

Individually ranking hundreds of boats into categories was simply too subjective. Hipgrave wanted a uniform formula that could be applied to any boat to calculate its drag as it moved through the water.

The parameters that matter most in boat speed are length and width. The longer a boat or skinnier a boat, the faster it goes. Hipgrave simply divided the length of the boat by its width to find its drag coefficient.

The next step was figuring out how much of a head start boats deserved based on this drag coefficient. To nail down the right ratio, Hipgrave hit the water for field tests.

The tests would be skewed if Hipgrave paddled harder in one boat than another, so he wore a heart rate monitor to ensure an even energy level. Hipgrave used a GPS to calculate his speed in each boat when using the same steady stroke.

Hipgrave performed his trial on more than 40 boats over several months — borrowing them from friends, the Nantahala Outdoor Center and sales reps. Hipgrave occasionally traveled to events to perform his test on demo boats.

“Any time spent on the water is time well spent,” Hipgrave said of the chore. Besides, it made training more interesting.

Hipgrave was finally satisfied with the formula, but there was still more legwork to go before the next Tsali Challenge. Calculating the drag coefficient for the hundreds of boats arriving on race morning would be impossible. So Hipgrave looked up the dimensions of about 350 of the most common boats, calculated the drag coefficient, and put them in a spreadsheet before the race.

When someone shows up with a boat not on the list, race organizers simply whip out the calculator and tape measure.

Last year the new boat handicap system was unveiled and went off without a hitch.

“I only heard one person grumbling compared to dozens of people before, so as a whole it worked well,” Hipgrave said. “Some of the main grumblers from the past thanked us.”