The (not quite) Mellow Dude

At 67, Dennis Conner's sailing life is a California dream, but if you want to discuss it, look out. A special Grand Prix feature in our July/August 2009 issue

February 18, 2010

Dennis Connor 368

Bob Grieser

Tony Soprano. When I first laid eyes on Dennis Conner in early April on a radiant Sunday morning at the San Diego YC, the image of the TV mob boss leapt to mind. Both are outsized, imposing men, but that wasn’t the only thing. Dennis-still the only sailor universally known by his first name, sailing’s equivalent to a Brazilian soccer star-was striding towards his big ol’ Chevy Suburban (Tony’s ride). His happy black lab, Benny, was dutifully at his side (Tony loved animals). And then there was the jaunty captain’s cap he was sporting (Tony favored a similar chapeau whenever he was aboard his powerboat, The Stugots, a name that Dennis could surely relate to).

Whatever the reasons, I couldn’t shake Tony from my thoughts. A larger-than-life character, it was the duality of his existence that made him fascinating. He was, by turns, charming yet scary, generous yet petty, insightful yet intimidating, genuinely funny yet bitingly sarcastic, incredibly successful yet vaguely dissatisfied, and remarkably intelligent yet continuously self-deprecating.

Only later, after hanging out for a while with Dennis, would I connect the dots and come to the conclusion that, yes, he and Tony shared more than a few similar characteristics. But only one of them is real, and ongoing, and as puzzling and intriguing as ever.


Over the years, as both a writer for this magazine and a former yachting correspondent for The New York Times, I’ve interviewed Dennis on several occasions. Ours is strictly a professional relationship, and I’m well aware that on the best of days he considers people like me a necessary evil, and on most others, a royal pain in the ass. (In somewhat gentler terms, he reminded me of this several times during the course of our time together.)

He rarely grants interviews these days (he reminded me of that fact more than once as well), so I was positively giddy when he agreed to spend a few hours with me. I harbor deep respect for the man and consider him a worthy champion and a sporting hero (albeit a complicated one), as well as a towering symbol of loss and redemption. I consider him an icon of sailing, a man going down in history for almost all the right reasons, a defining emblem of an entire era. But no matter what one thinks about Dennis-and it seems everyone has an opinion, not all of which are floral bouquets-there are certain salient facts that are utterly beyond reproach.

He is a four-time America’s Cup winner and the only skipper to lose it and win it back. He’s appeared on the covers of Time and Sports Illustrated and earned the sobriquet “Mr. America’s Cup.” He’s won countless world championships and an Olympic medal. He can still raise hell in an Etchells. Many consider him the greatest racing sailor of all time, and one must be quick and stubborn to argue the point.


And there’s this: These days, as either a partner or outright owner, he reigns over a fleet that would be the envy of any sailor. His San Diego business, Dennis Conner’s America’s Cup Experience, includes a pair of America’s Cup Class yachts and a stunning replica of the original Cup winner, the schooner America, the helm of which he loves to take. An East Coast enterprise based in Manhattan’s North Cove Marina employs a pair of 52-foot racing sloops for charters and corporate team building. He owns four Etchells, two of which reside in New Zealand and Australia, respectively, and remains a fierce presence in the class, where these days he enjoys his most rewarding, competitive sailing. He takes his Farr 60, Stars & Stripes (ex-Numbers), out for the SDYC Wednesday-night summer series and the annual jaunt to Ensenada.

Then there’s Brushfire, the classic, impeccable, Sparkman and Stephens-designed, 51-foot woody that’s tied up a stone’s throw from the yacht club bar and which serves multiple roles as a race boat, office, and retreat (it’s his second antique wooden boat in recent years, the first being the 1925 Q-Class yacht Cottom Blossom II, which he restored and then raced on the Mediterranean before selling).

I’d heard that Dennis spent loads of time aboard Brushfire, usually with Benny at his feet, sometimes baking cookies or making lunch for his crew and friends in the comfortable galley. As a warm, fuzzy picture in the mind’s eye, it had a lot going for it, and before our meeting I’d begun imaging the vintage-2009 Dennis as a mellow dude chilling on the waterfront, the lion in winter kicking back on his wood boat and finally finding peace and respite after all the long, grueling campaigns.


This fantasy, in some (but not all) ways, proved to be as fictional as Tony Soprano. That was clear almost from the very moment he nodded toward the Suburban and said, “Get in.”

The next couple of hours were incredible; he was as gracious a host, as interesting a companion, as any you’d hope to find. We ate breakfast at a fine little diner in Ocean Beach where he ordered “the usual” and knew all the waitresses. We took a long drive through Point Loma, past the modest little house at sea level where he was raised and the much more substantial residence up the hill that he now calls home. We stopped at a headland where he urged me to get out and sniff the salt air. “The Pacific looks very pacific today,” he said.

We drove up through Fort Rosecrans and pulled over to take in the wide vista of San Diego Bay and the downtown skyline. Dennis spoke knowledgably and even passionately about the city’s geography and history, the voyage to its shores by European explorer Juan Rodriguez Cabrillo, the changes that had unfolded over the years. When it comes to his beloved hometown, Dennis should run the Chamber of Commerce.


“It’s the nicest place in the world to live,” he said. “I’ve been around. You’ve been around. What’s a better alternative, especially in America? New Zealand’s nice, but it’s too far away. This is the best place in the world.”
Back at the yacht club, as we walked toward the docks, I thanked him for the tour, which had basically blown me away.

“It’s all relative,” he said, invoking an oft-repeated line. “Imagine what it would’ve been like if you were with someone who knew what they were talking about.”

I thought he was kidding, though I don’t know him well enough to be sure. Whatever the meaning, it certainly introduced a new tone to the conversation.

Over the next few days, I’d run into a couple of people who do know Dennis well. Troy Sears is his partner at Dennis Conner’s America’s Cup Experience. “He’s very involved in the day-to-day operation, but not hand’s on,” Sears said in America’s vast saloon, right before heading out on a whale-watching sail from a downtown pier.

“He’s a very early riser. I’ll get up in the morning and I’ll have an email from him, time stamped at four or four-thirty a.m. He’ll have a whole list of ideas, or questions, or things we could do better. Typically, they’re all very good suggestions.”

I asked Sears about Dennis’s reputation as a stern taskmaster. “I’ve found that once you’re inside his inner circle, he’s very warm and he cares,” he said. “Do I see him get stern? Yeah. But not typically to the people in his ‘family,’ if you will.”

For nearly two decades, Jack Sutphen got to see and know Dennis as few do, as his sparring partner and the skipper of his trial horses in one Cup campaign after another. Now 91, Sutphen remains sharp as a tack and his stories about life with Dennis, on a daily basis, are rich, warm, funny, and endless.

“What’s disappointing is that Dennis does a lot of nice things and gets no credit for them,” said Sutphen. “One day in Australia [in 1987] he comes down to the dock and he’s got a little kid with him, all dressed up in [Stars & Stripes] foul-weather gear. I said, ‘Who’s this?’ and Dennis says, ‘It’s my newspaper boy. And he’s going to sail with me today.’ And he had him out the whole day, sailing, this kid we’d never seen before.

“Everything he’s done for me has been wonderful. So I have tremendous respect for Dennis and I like him tremendously. But he can turn around the next day and walk right by you and your wife and not say a thing. He’s focused on something else. He has tunnel vision. But that’s what people who don’t know him remember about him.

“One of his great strengths is that he’s a great guy to sail with,” added Sutphen. “Anybody who sails with him wants to sail with him again. Look at the pictures of the old Cup teams. Year after year, the same guys. There’s a lot of loyalty with Dennis on both sides. I can’t make the point strongly enough.”

After my tour of San Diego, we stepped aboard Brushfire. The varnished cabin house was exquisite. The topsides gleamed. The entire boat was gorgeous, Bristol fashion, a work of art. The only thing that seemed out of place was the dish antenna mounted off the cockpit, feeding the satellite signal to the flat-screen TV below.

“I want to see what’s happening with the NASCAR race,” said Dennis, flipping it on.

The next hour or so, however, was more like a tennis match than a stockcar race. I’d serve up a question, and he’d volley back an answer, sometimes with a bit of pace, sometimes with a little spin.

On Brushfire’s PHRF rating: “Ever hear of the Tall Poppy Syndrome? That’s why I get a rating that’s six seconds a mile less than I should. If I can’t win, who should? The boat’s in perfect shape. The sails are perfect. I’ve got the best crew. So what do they do to level it. They give me a higher rating.”

On wood boats: “There’s something about old wooden boats. It’s hard to explain to people who’ve never experienced it, or don’t have gray hair. They think fiberglass is the smell a boat should have. They don’t understand the warmth and beauty of wood.”

On the America’s Cup: “I reckon old guys like me remember the old days, when it was a sport. It wasn’t a business. It was a sport. That was then. It’s a big business now. It changed. Some people are having trouble grasping that change. That’s their personal problem. These days it’s all about litigation, power, and juice. It’s a game that plays to (the billionaire’s) strengths. It’s not about who’s the best sailor. The best sailors aren’t in the America’s Cup.”

On mellowing out: “Am I less competitive? I would think so. You still do the best you can. But it’s not life and death. The other thing is, it’s not as satisfying to beat someone who isn’t putting the same amount of effort into it.”

On the end of our interview: “How much longer is this going to take? This is all personal anyway. It’s nobody’s business. What good can it do me? I did this as a favor to [San Diego-based photographer] Bobby Grieser. A good deed never goes unpunished.”

As we walked down Brushfire’s dock back toward the club, a pair of very attractive women (“cougars” in the modern vernacular), dressed to the nines, hair perfectly coiffed, stopped Dennis cold. They introduced themselves and babbled at him for a moment-honestly, they seemed barely coherent-and after Dennis paid them a compliment and wished them a pleasant day, everyone carried on.

A moment later, as we parted ways, Dennis made an amusing comment about “desperate housewives” and I said that I had to hand it to him. Good-looking strangers, even crazy ones, rarely halt me in my tracks and flirt shamelessly.

“Man, it’s good to be Dennis,” I concluded.

He nodded pleasantly. Against long odds, I’d finally grasped the obvious.

“I told you it was,” he said.


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