07/19/2013 04:43 pm ET Updated Sep 18, 2013

A Cup of Caen: Surfers, Snowboarders and a Garage


My first ride on a competitive sailboat was in 1983. A racing event called the Big Boat series was in town for the week, and I was desperate to get one of the racers. My friend Grant Settlemier told me just to grab my foul weather gear and hang out on the docks. With San Francisco's prodigious fall winds, teams would be looking for "rail meat" -- someone who would sit on the edge of the boat to help keep the boat level and would promise to not touch a single thing, except for the rail.

I was lucky to bargain my way onto one of the hottest boats of the year, Scarlett O'Hara, where indeed I sat on the rail and got clobbered by wind and water. My death grip on the rail made it easy to keep the promise not to touch anything. It was the first time I had raced on the bay, and, even in my most robust outerwear, I was laughably underdressed, wet, freezing and shivering by the end of the day. Of course I didn't let on, smiled through chattering teeth, and got off that infernal boat as fast as I could.

But I had loved every second of it, and so began years of racing on San Francisco Bay. Sailing had the physicality I liked about rugby, the relationship to nature that makes trail running so enjoyable and the never-ending strategy of trying to figure out what the water, the wind and your competition was up to every second around the course. I loved the fact that you could sail a leg once, and then the next time the weather and San Francisco Bay had completely changed it without telling you. And I loved the bluffing and blustering of fifteen boats all trying to hit the starting line at the same time, with the constant yelling and screaming between crews. Then our skipper would yell out "we're racing!" and we would slam all the sails in, winches and handles flying, and then scramble to the high side as the boats powered up and surged across the line like race horses released.

And I loved the people I met sailing, people from every walk of life, and from every corner of the Bay Area. One year campaigning on a Santana 35, we would all park in the cheapest parking lot we could find in Sausalito, and then the owner would come get us in his beat up Toyota minivan. We would throw our bags onto the sails piled on the floor, then flop on top of the entire smelly, wet mess, and careen down the road to the docks. Some of my happiest memories sailing are of bouncing around in that van, hyped-up on caffeine and adrenaline, excitedly talking about the impending race.

So it burns me up something fierce when I hear people talking about the America's Cup as if it' a bunch of silver spooned dilettantes flying around the world and jumping into their expensive cars with collars flipped up. Like any sport, the owners are billionaires, and yes, the audience includes some ridiculously wealthy people, but the sailors themselves are not of that ilk. They are some of the hardest-working athletes in the world, who do this more for the love of the sport than for the paycheck. And they better love the sport, because any backup quarterback in the NFL makes more than an entire America's Cup crew.

As people's exhibit number one, I offer Monday night. I got the call that day asking if I wanted to go have dinner with some of the Oracle crew. So, that evening I found myself standing in front of a nondescript door in the Mission. Dinner that night was in a converted garage, and, in addition to some team members, there were some entertaining visitors, Jamie O'Brien and Travis Rice.

Jamie and Travis are well known to the X-games generation. Jamie is famous surfer who grew up down the road from the legendary Banzai Pipeline. He now travels the world as one of the leading professional freesurfers. Travis Rice is a snow boarder -- a big mountain freestyle legend. Some professional athletes hang out with supermodels and rock bands. The America's Cup guys like to hang out in garages and throw back beers with surfers and snowboarders. No caviar or champagne in sight.

So, why were these two funny, cool athletes hanging out with a bunch of sailors in a garage? Because earlier in the year they both had the opportunity to go out on the AC45 catamarans. I think it's pretty amazing that this is happening, and that the Oracle Team is willing to bring them into the family. I corralled both of them, because I was interested what two guys who are experts when it comes to speed thought about these boats.

"It was an opportunity that came through Red Bull," said Jamie. "I sailed a little before so I thought this would be super cool and it was an opportunity that may never come up again. But I didn't really know what it entailed until I got here and did the practice with the crew and the work outs and the sailing. And it meant so much more to me. My sailor friends at home were over the moon about it."

I asked him what was the most surprising thing about the boats. "We did 27-28 knots and I couldn't imagine going out and doing that on a sailboat like that, we were flying. And I want to go out on a 72... I can't imagine the speed on that boat. The whole hydrofoil thing is super amazing."

This was also echoed by Travis. "The coolest thing is how well-oiled the crew is. The 45 without the crew is just a cool piece of space age material. But when you actually see the five guys in unison running the boat and they don't even have to talk to each other, how in tune everyone is to the task at hand, to me that was the coolest thing by far about the 45s."

As a life-long sailor, I thoroughly enjoyed listening to these two dudes of extreme sports using the word "cool" over and over again to talk about the boats. But watching them laughing and having their beers just showed how, the more the Cup becomes about the boats, the more it remains about the sailors. Billionaires come and go in this sport, but tomorrow some regular person will be standing on a dock somewhere with their warmest gear, and they will get a ride. And they will fall in love. And yes, that is pretty cool.