The one that got away: How Paul Cayard won the 99th Bacardi Cup

Paul Cayard started sailing at eight years old in a tiny El Toro dinghy on San Francisco Bay. Nearly six decades later, he's still at it – and still winning.

His career spans every corner of the sport: seven America's Cups, two Olympics, eight world titles, two circumnavigations, and the distinction of being the first American to win the Whitbread Round the World Race. In October, he was inducted into the America's Cup Hall of Fame, then in December, he collected his second Rolex Yachtsman of the Year award.

Of all his achievements, Cayard has said his most prized victory is his 1988 Star World Championship – the title that launched his professional career and the boat class he kept returning to through decades of offshore racing and Cup campaigns because, as he put it, "it grounded me in the skills."

Last September, at 65, he won his second Star Worlds in Split, 37 years after his first. Now 66, he arrived in Miami last week for the 99th Bacardi Cup as the reigning world champion, sailing with German Olympian Frithjof Kleen.

But the Bacardi Cup itself? That had eluded him for 45 years, and the fleet assembled on Biscayne Bay this year offered no easy path.

77 boats from 16 nations, including 17 Olympians, six Olympic medallists, 14 Star World Champions. At the top of the list: Mateusz Kusznierewicz and Bruno Prada, six-time consecutive Bacardi Cup winners, the benchmark against which everyone else would be measured.

This is how the week went down…

Monday delivered 15 to 17 knots and what Kusznierewicz called "champagne conditions" – the kind of Biscayne Bay day that makes two hours of long-course racing feel like a privilege. The opening beat stretched over two nautical miles, the left side paying early before the breeze began to oscillate across the course.

At the front, Cayard and Kusznierewicz traded the lead through the final legs. On the last beat, the leaders split one more time. Kusznierewicz and Prada worked the right side, gaining with every cross, and appeared poised to roll over Cayard in the dying moments of the race. Then the breeze swung right. Cayard could suddenly almost lay the line. He tacked, held his lane, and crossed first by the smallest of margins.

"It was a beautiful day on the water, but very tactical," Kusznierewicz said. "On the final beat we were waiting for a right shift. It came just a little too late."

Cayard knew how close it had been. "Mateusz was physically ahead of us. If I had gone to him, he would have crossed me. But the wind had shifted so far right that we could nearly lay the finish. We tacked and managed to hold on."

Third went to Robert Scheidt and Austin Sperry, another team with unfinished business in the Bacardi Cup. Game on.

Tuesday's race hinged on the opening beat. Cayard, Kusznierewicz and Scheidt punched out together on the left side of the course, built leverage over the fleet, and never looked back. From there the trio extended, turning the race into a private battle as the rest of the fleet fought for what was left.

Cayard rounded the final gate first, Kusznierewicz close behind and immediately tacking away, Scheidt holding third. Two hours of racing, 13 to 15 knots throughout, and the same three boats at the front. Another bullet for Cayard.

"Can't start Bacardi much better than that," he said. "But it was very tough racing out there with Mateusz and Robert: very physical in 15 knots. It's a two-hour nonstop physical exertion."

Despite the 1-1 scoreline, Cayard was careful not to get ahead of himself. "It won't be any different tomorrow, and it won't be any easier. Long way to go."

Wednesday brought more breeze and another wire-to-wire performance from Cayard and Kleen. They started on the left, worked toward the middle, then returned left as the first beat developed. At the windward mark it was Americans across the top three spots: Cayard, Brian Ledbetter, Eric Doyle. From there, Cayard simply managed the fleet.

"It was just beautiful sailing – as good as it gets on Biscayne Bay," said Doyle, who finished second. "Paul stepped out a little bit on the final leg and showed why he's leading the regatta right now."

Three races, three bullets. Hat-trick complete. The gap was opening up, with Cayard and Kleen on 3 points, Scheidt and Sperry on 10, Kusznierewicz and Prada slipping to 13.

But if anyone thought the regatta was already decided, Scheidt – five-time Olympic medallist, one of the greatest sailors of his generation – begged to differ.

"The game is still pretty open."

Thursday brought the first crack in Cayard's armour – or rather, the first sign that Scheidt wasn't going anywhere.

The five-time Olympic medallist controlled the race from the front, finding clear air early and never relinquishing it. Behind him, Cayard and Diego Negri traded pressure through the final legs, each looking for the moment to strike. Scheidt held on for the win. Cayard limited the damage with second, his streak broken but the lead intact.

"There are a lot of world champions, a lot of top-quality sailors in this class”, said Cayard. “Everywhere you look you are in a battle.”

"Paul is on fire," Scheidt said. "He's having a super great regatta. Not making any mistakes."

Cayard, for his part, betrayed no concern. "Our boat speed is good, so we're not changing much," he said. "We try to stay clean on the start and let our speed work for us. Then halfway up the first beat we try to find where everybody is and make a strategy from there."

After four races: Cayard on 5 points, Scheidt on 11.

Friday belonged to Scheidt. In 12 to 15 knots on the turquoise waters of Biscayne Bay, the five-time Olympic medallist controlled the race from the start and never looked back. Back-to-back race victories had transformed the regatta.

Finishing in sixth, Cayard's lead had been cut to three points. Scheidt needed to beat him by three or four places in the final race.

With the discard now applied after five races, only Cayard or Scheidt could win the 99th Bacardi Cup. Scheidt's plan was straightforward. "Tomorrow, we'll try to get a good start and hopefully be ahead of him on the first cross," he said. "The first cross will be very decisive."

Going into the final race, Cayard still had a throwout to play with, meaning he could discard his worst result. Scheidt had no such luxury.

"He has to be first or second in the race. If he's not, then he doesn't win," Cayard said. "The logical thought is that if I have the opportunity to match race him and push us both down to twentieth, then the race just got a lot easier for us. Exactly how and when we might execute that, I have to think about it and dig deep into my America's Cup experience to decide what the smart thing to do is."

In 1992, a 29-year-old Cayard skippered Il Moro di Venezia to the America's Cup final in San Diego. Outpaced by the defender America³, he won just one race in the series – but he won it by three seconds, employing classic match racing tactics to produce what was then the smallest winning margin in Cup history.

34 years later, on Biscayne Bay, the same instincts kicked in.

Ten minutes before the start, he engaged. For five minutes before the starting sequence even began, the two boats match raced – circling, hunting, testing. Scheidt needed room to race, and Cayard made sure he didn't get it. When the gun fired, both boats crossed the line 100 metres behind the fleet.

"We got on Robert and just made his life basically miserable," Cayard said. "Robert and Austin had some difficulties in the boat handling, and we both crossed the starting line way behind the fleet. So I would say 90 percent of my job was done right there."

Cayard went right while the fleet poured left, keeping close tabs on Scheidt as the two legends fought their own private battle. At the windward mark, Cayard rounded in 26th while Scheidt was 30th. For a man who needed a top-two finish, that was as good as over.

But Scheidt refused to go quietly. He broke free, found clear air, and launched one of the great comebacks – passing boat after boat, clawing his way through the fleet to finish in 10th. A heroic effort, but not quite enough.

Cayard and Kleen could relax and let the points do the talking. The 99th Bacardi Cup was theirs.

"This means a lot to me," Cayard said. "I've gotten second many times. It was the one thing I hadn't won in the Star class. Bacardi's Eddie Cutillas keeps telling me, 'Next year is gonna be your year.' The pressure builds and builds. I'm grateful that we got the job done. A two hundred pound gorilla fell off my back."

Kleen, ever the pragmatist, offered his own take on the week. "Sometimes you have to eat some shit. Sometimes you have to win with just two metres instead of two minutes. But Paul likes perfection."

"For the first time in a long time, we have a new champion,” said Eddie Cutillas of Bacardi USA. “This victory in the Bacardi Cup is a capstone for Paul's very successful career.”

Asked about the final-race drama, Cayard grinned. "When I'm dead, they'll still be playing that one."

Behind them, Kusznierewicz and Prada claimed bronze after winning their own battle with Negri and Lambertenghi. But this was Cayard's week, and everyone knew it.

"I don't think you have harder sailing than what you find in the Star Class," Cayard said at the start of the week. "If you want to find out if you're a good sailor, you need to sail in the Bacardi Cup with the Star Class – then you're going to find out."

It took 45 years and more second places than he cares to count. But at 66, Cayard can finally call himself a Bacardi Cup champion. One year before the centennial, there’s a new name etched into history.