Sailboat Racing: Plays We Run on and Off The Water

I love sailboat racing. It’s an obscure and little-understood sport — my secret connection to wind, water and a cherished community of irreverent frenemies.

My boat is an Etchells, a complex, 30-foot design that’s raced by club amateurs like me and Olympian and America’s Cup athletes alike.


Her name is Playmaker (shown, above, with crew Ron Thompson and pro Robby Brown at the 2014 World Championship). Most assume it’s a bogus tax-deduction for my consulting practice or just another bad boating pun. But after a recent weekend of on-the-water jousting, I realize that my hobby is a showcase for my professional interest in strategy and influence. As such, I wonder if I should practice on the water what I preach in the boardroom. Here are a few examples from a frustrating yet fun regatta:

YEAH, I HEARD YA: Most sailboat races involve the rounding of bobbing buoys. And when the competition’s tight, it’s a traffic jam at the turns, better known to skippers and crew as a pinwheel or clusterf–k. There are rules of course to ensure fairness and sportsmanship and, like pickup basketball, sailors are expected to call their own fouls.

Such was not the case when, approaching the right leeward “gate,” two boats behind me thought to ignore said rules and cut the line that my boat and others had formed. The nearest of the two, I’ll call her skipper Muffy, was ordered not to. “Don’t go in there!” I warned. My play was a challenge, though one wonders if she took it as a bait, pushing into the obedient pack and infuriating captains of the cluster she’d just created.

Muffy was protested and made one of two required circles as punishment. When asked at the dock what she was thinking, the reply was, “Yeah, I heard ya yell ‘don’t go in there,’ but I had a bunch of traffic issues…” (Translation: I thought you were sailing like such a piece of sh-t that you were gonna round wide and I’d just stick my bow in there and roll your sad ass.) This is a distraction device and, by a happy coincidence, a play named for the time-honored, rotted fish, a Red Herring.

DUDE, LEARN HOW TO SAIL: Muffy’s hedging was child’s play in comparison to the derring-do of two other competitors who thought also to flout the rules. From inside the zone, an area of expected good behavior, my port tack rivals barreled toward the windward mark, ignoring Playmaker and one other close-hauled starboard tacker. They had no rights, they each knew, but still tried to bully their way around the buoy. It was a near disaster.

“Foul!” and “Protest!” echoed as we shoved tillers to avoid pricey repairs, our trimmed sails now flogging. No circles were sailed, signaling a standoff, a dare of sorts to sacrifice Sunday’s de-rigging and barside banter. But it had happened too often before, so I took the dare and, as they say in sailing, took them to the room.

“Next time, hit ’em,” was the shoreside advice of a veteran skipper, beer in hand. “Just tap ’em and they’ll get chucked,” he winked, referring to the protest hearing I had just endured. His play was the ping, an off-the-record hint of how the game is really played.

As for the offenders, their play choices varied. Biff, I’m inclined to call him, had showered, shaven and headed for home. (Translation: I don’t do protests.) His play was a pass. The other, a local we’ll call Rocko, was more determined to debate, arguing along with his crew that he’d had plenty of room and time to turn his white sloop in front on my boat’s signature pointy bow. (Translation: Dude, learn how to sail.) His play was a recast of the gamble and, incredibly, he was found innocent. Though it mattered not to his standings, Biff was thrown out for having forced the fracas.

Asked later about the verdict, one veteran judge advised, “Next time, get better witnesses.” His play was the now-familiar ping, a suggestion that my crew were never believed. (What is surely true is that mine were never coached, and Rocko’s were. Lesson learned.)

As in business, politics, pop culture or even the rare sport of sailboat racing, people run plays. As these vignette’s attest, they do so with a variety of intentions, but always to advance a position or agenda through the 24 strategies of influence.

A moral to the story, at least in the red-meat world of one-design Etchells racing: Rules might keep you in the race. But running plays will keep you at the front.

Licensed photo and credit: Sharon Green, Ultimate Sailing

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