History happens. Sometimes, it’s watery history, sometimes dry. This is watery history.
In 1983, Australia broke America’s 124-year America’s Cup winning streak with it famous “winged keel” — a breakthrough sailing speed innovation. Even so, U.S. skipper Dennis Conner lost only by a whisker to the much faster Aussie boat, using wind shifts and aggressive tactics to stay tied until the final minutes of the very last race. But now The Cup was going down under, mate …
By 1987, Conner was headed for Perth and out for reclamation revenge.
Conner wasn’t alone. A well-funded gaggle of top US racers — including stars Buddy Melges, Tom Blackhaller, John Kolius,Gary Jobson et al — tried to shove New Zealand’s Chris Dickson out of the way as the early leader to win the Challenger’s slot to go up against Cup Defender Australia in the final. As the summer wore on, all eyes were on Dickson’s Kiwi Magic. Through dozens of one-on-one match races, the Kiwi’s became the boat to beat. They were roasting everybody they battled, including Conner.
Now, back to Dennis. His boat was Stars & Stripes and he had a secret. Since ’83’s surprise winged keel, everybody was spying on each other’s boats, especially Kiwi Magic. Conner realized early on that his boat was slightly faster than the others, including Dickson’s. Now he had a secret and a plan. He started sandbagging right away. He would win just enough races to get into the final 4. He wasn’t highly regarded as a threat to win the whole thing. He would hold his boat back by not trimming in his sails all the way. He won plenty of races, but not by much. New Zealand was first by a mile to get into the Challenger Final.
The winds off Perth, in a little town called Freemantle, were notoriously ferocious. The wind was called The Freemantle Doctor and came in like the flu the same time every day at around 20-25 knots, which is sliding, meaty whitecaps. Conner and his syndicate had built their boat just for this. Off came the gloves, out came the race horse, and Stars & Stripes began to chew up the competition, race by race.
So did Dickson — but not as one-sidedly. The two rival teams got to the Challenger Final for a best-of-five series. It wasn’t even close. Stars & Stripes won 3-1. Dickson only won a race because Conner’s spinnaker exploded in the wind in the lead and he coughed one up. But the next day he dusted off Kiwi Magic in a horizon job.
Now in the Cup Final, it was to be an Australian beer brewer, Alan Bond, up against the drapery maker, Dennis Conner. Everyone remembered what had happened the last time. But surprise, surprise, out of the box, Stars & Stripes ground up and spit out the supposedly faster Australian Kookabura. In four straight races, Stars & Stripes dismantled the Aussies, winged keel and all. Drapery money had bested beer money! The experts couldn’t believe it! The home crowds, who lined the shores and docks, were in tears. America’s Cup was coming home again! Conner had beaten New Zealand, the Aussies and the Ghost of ’83! Revenge, glory, brilliant speed and sandbagging!
One of the best America’s Cups ever!
Now cut to April Fool’s Day, 2026, just last week. I had been invited to fly down to Hilton Head Island to be a passenger on the aforementioned Stars & Stripes. Built in 1986, it had just turned 40 and it was still sailing. Who knew? It was like meeting a Greek god.
This was the Champion of the World who had stood the whole world of sailing on its head for four years. Like Muhammad Ali did to boxing!
At the dock, it looked exactly like it had in all those video tapes I’d set to record at 2 a.m. back then — cuz it was the other side of the world. That special gun-metal blue coloring, the double steering wheels — right and left — the towering white mast. It was like a ghost from my past.
But I knew all about it. I’d watched the races repeatedly back then and knew the background story about Dennis and the Kiwis.
I could talk a good game. And did. So much so that, after about ten minutes under way, the cCaptain turned to me and said: “You seem to know all about it. So, ready to drive?” My body instinctively wrapped itself immediately around that wheel in case someone else might have thought he meant them. But, surprise, Stars & Stripes was a tank! She had been built for 25 knots and it was blowing 6. The wind was all over the place: left, then right, then up and down in speed. But you could feel the thoroughbred speed built into her. Finally, a steadier breeze piped up and we were zooming. Apparently, we passed a shark, dolphins and several manta rays, but I never looked away from the course ahead out of pure fear of failure.
History had dropped right into my lap. The wonderful captain let me drive for nearly a half hour. It was a tank alright, but it was my tank full of watery history.