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The Myth of Going to Windward

If you are a cruising sailor, I suggest you sit down. I have some shocking news to convey to you. It is not just your boat that doesn't sail to windward - none do. Zero. Not even racing yachts. Have you ever wondered why America's Cup boats have their underbody shrouded by fabric? That's to conceal their painted-to-blend-in propellers and their cleverly-concealed underwater exhaust outlets.

This isn't easy to confirm. The moment I broached the subject to Olympic-medalist Peter Housberg of St. Thomas - he hung up. Ditto Dennis, Paul, and Kenny. Russell Coutts even blocked my emails. James Spithill fainted dead away. But I finally managed to track down a disgruntled 'B-team' member of Dawn Riley's old Bill Koch-financed American's Cup Challenge (from San Francisco) who was willing to violate the 'old boys club' rules.

"Yeah," Loose Lipped Lucy admitted, "American's Cup boats really do have very quiet 'stealth' engines. The problem - at least from the female gender's point of view - is that the America's Cup has been male-dominated for so long that these sort of, ahem, prickly facts are now commonplace. Winning is somehow … I dunno, connected to their penises. Once the first guy did it, and appeared to be victorious - well, then all the other testosterone-fueled sailors joined in. That's one of the reasons that yachting is so exclusive and elitist - so the common man doesn't realize he's been had."

"But," I said, my jaw on the floor. "Isn't this cheating?"

"Sure," said Lucy, "and it would be labeled as such if a woman did it. But with a man - well, let's just say they have a different moral deck. They sort of gloss over the moral complications of anything sports-related. This 'stealth-engine' issue has been going on for so long now that it has been sort-of institutionalized as '… pushing the envelope' of the rules rather than out-and-out cheating."

"But how is the winner determined if not on the water?" I asked in a wounded, 'Tell me it ain't so, Joe' tone of voice.

"That's easy," Lucy said. "The accountants huddle in a room - and decide who has the most money. Arthur Anderson used to be the judge of choice, but now it is Price Cooper Waterhouse since Arthur Anderson had its whistle blown."

I decided to check if this was just as true in the cruising community. To do so, I contacted a yacht designer at Vulgaria Yachts (who preferred to speak off-the-record).

"Our yachts are designed on the Shoe Box model," the designer said. "This is pretty much the industry standard. Let's face it - there's a lot of room in a shoe box, and it drifts downwind well - which is, pretty much, what people like about their boats. Anyway, our industry is a tad like the GMC of Detroit was in the 1950s. We play with porthole design and cove stripe styles - and call it a 'whole new experience' in ocean sailing."

"Hey," I said in his defense, "Your boats are ugly, sure, but they ain't THAT ugly …"

"Oh, yeah," the designer acknowledged awkwardly, "we pinch in the bow a tad, make a cut-out for the open transom, and play with the sheer a bit … we tweak the design just enough so our boats look like a yacht should and aren't confused with, say, a cardboard carton or a boxcar."

I next turned to a well-known scientist at the Scripts Institute for Liquid Fluidity for some off-the-record conformation as well. "It's true, Fatty. Sailboats don't actually motivate themselves to windward without a mechanical mechanism - what the layman would refer to, typically, as an inboard engine."

"… but," I sputtered, "we were told that keels somehow spurted the boat forward against the wind …"

"Well, we had to say something, didn't we? We figured the simpler and more basic the explanation, the better. But the true fact of the matter is that vessels blown down wind can't sail against that very same wind - just as, for instance, there's no perpetual motion. Anyone can prove this by taking an almost endless number of different-shaped floating objects - and tossing them into the water in a strong breeze. They all end up downwind, don't they?"

"This seems so incredible to me," I said. "I mean, that the America's Cup boats had engines … Wouldn't we have heard the auxiliary power running?"

"Well, I'm ashamed to admit that respected scientific research institutes such as ours were paid hundreds of millions of dollars by Ellison, Koch, and Conner to design and construct ever-quieter engines AND to make the ambient shipboard noise intentionally more, well, noisy!" "Huh?"

"… did you ever notice how, during the America's Cup, there is so much wind-whistle in the audio? That's because it's mostly computer generated. And the boat's rigging is set up to obscure the engine sounds as well - all those flapping sails, banging halyards, and fluttering leeches."

"… and nobody blew the whistle?"

"Frankly, no," the scientist admitted. "We eggheads and geeks have the same moral standards as the Average Man on the Street - which is almost exactly zero. Everybody was making money. It was a victimless scam. If poor people wanted to allow themselves to be tricked into believing that rich people could do things normal human beings couldn't - what harm was there in that? Hasn't royalty and organized religion been doing the same thing for centuries?"

"It is just … hard to grasp," I said. "I mean - the audacity of such a world-wide scam!"

… perhaps you're questioning the wrong guy," said the scientist. "Perhaps you need to talk to a shrink, not a by-the-numbers dude like myself."

I followed his advice, and set up a Skype call to Fritz Pearls III, grandson of the founder of Gestalt.

"… think codpieces," he said quietly.

At first, I didn't get the connection. Then I saw the beauty of his out-of-the-box argument.

"… so it's like that," I said. "… wild!"

"Exactly," Pearls Junior Junior said. "Think breast implants. Breasts implants, for instance, are just permanent, in-the-body codpieces for women. Everyone knew that codpieces were fake - but they empowered the man. Ditto, the woman with 44D's. And some of these self-deluded, self-empowered people - delusional or not - are able to harness their empowerment into actually becoming more successful than their peers - celebrities, if you will.

"… so you're saying …"

"… I'm saying that men want to be winners - at all costs. They want to be Big Dicks. So they lie about their penis size, their yacht's stealth engines, and how many times they've had plastic surgery. Yes, they used to wear codpieces. Today, many successful female entrepreneurs have surgically- enhances breasts. Donald Trumps lies about both his hair AND his bank account. Today there's so much fibbing/puffing/spinning/exaggerating going on that an honest man seems … well, so dramatically lacking in almost every regard."

"But this is all deceitful, isn't it?"

"Perhaps," said Junior Junior, "or perhaps this all just highlights the difference between winners and losers. Winners want to win, and they go to the extra trouble to cheat to enable them to do so. Is this a bad thing or a good thing? I dunno. Losers, on the other hand, just passively accept reality. They don't struggle against their fate. They accept all the dreary realities of life in a Zen Buddhist way - which is why super-fit yogis are always beaten on the battlefield by cigar-chomping, beer-swilling, meat-reeking, pot-bellied soldiers."

I was so stunned I didn't know what to say.

"Cheating isn't necessarily wrong - not if it gets you ahead in life," said Junior Junior. "Or, at least, that's the new social paradigm, Fatty. Take it from Wall Street - those dudes know cheating! Or ask an investment banker. Winning isn't something you do, it is a moral choice you make - a path you take. And, once you decide to side with the winners, there's no going back to being Little Miss Goody Two Shoes ever again. That is why the Congress of the United States opts out of its own social security problem - because it likes to make laws for others that it is loath to chafe under itself."

I realized, sadly, that this was true. I'd always claimed my boat went to weather like a witch - and yet never actually attempted to damage my ego by attempting to prove it. This is what is commonly known as maturity.

The truth, of course, sometimes hurts. But acknowledging it is always the right thing to do. I suddenly felt ten times lighter while sailing … well, drifting down wind, actually. For the first time since I began my career as an offshore sailor, I feel no shame in cranking up my yacht's engine. And I even renamed my vessel in honor of my recent Deep Realizations of the True Nature of Mankind. We're doing great, my boat and I. Next year I'm even gonna change Shoebox's propeller to a four-blade!

Editor's note: Cap'n Fatty and Carolyn are currently off their meds in the Med. Their latest book, just released, is entitled Somali Pirates and Cruising Sailors. Visit Fatty's website for details.

Cap'n Fatty Goodlander lives aboard Wild Card with his wife Carolyn and cruises throughout the world. He is the author of Chasing the Horizon by American Paradise Publishing, Seadogs, Clowns and Gypsies, The Collected Fat, All At Sea Yarns and Red Sea Run. For details of Fatty's books and more, visit

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