At the 2019 Snipe Worlds in Ilhabela, Brazil, I’d heard a lot about the Brazilian sailor with the nickname “Gigante.” Given the crew is usually the smaller of a Snipe team, and with a name like that, I’d always assumed he was the bigger of the two when I saw them together. Two months later, however, as we walk side by side across the parking lot of the Nassau Yacht Club in the Bahamas, we’re practically eye to eye. It’s Brazilian sarcasm, he tells me, with an engaging grin. “I’ve always been small, since I was a child. So, it’s a kind of joke.”

Henrique “Gigante” Haddad, the relatively unknown 32-year-old Snipe World champion, groomed in the rich South American one-design sailing scene, is one of several rookies in the Bahamas attempting to make a name for himself among the elite of the once-Olympic Star Class. He’s an invited guest at the annual Star Sailors League Finals, and on the day we meet for a late-afternoon coffee, he’s not only survived the qualifying races, but he’s soared into the top 10. Admittedly, he’s not much of a Star sailor, but over the past few days, he’s proved himself plenty capable of competing with the other invited skippers, as well as the legitimate giants of the Star class. For the regatta, the diminutive skipper teamed up with crew and countryman Henry Boening. Where Haddad lacks street cred in the Star, Boening is highly decorated. “Magilla,” as he’s known, has twice finished second in the SSL Finals, as well as the 2019 Star World Championship.

The Star Sailors League Finals is an invitation-only regatta, contested in Star boats. Its stated goal is far more inclusive than the choice of boat might suggest: to celebrate the champions, or the “stars,” of sailing and also to “­create those of tomorrow.” That’s how the tomorrow guys like Haddad get their invites. The League Finals are four days of racing on Montagu Bay, where 23 teams are winnowed to 10. On the last race day, three knockout races determined the final four, and after that, it’s a one‑race‑wins-it-all shootout.

The first pool of coveted invitations goes to sailors at the top of a league-managed global-ranking list, which is updated weekly and includes more than 50,000 sailors from 36 classes and disciplines. The next group of invited skippers have either recently won a major event or hail from a developing country (or both), ensuring a range of experience. For this 2019 edition, Haddad is one of them. The other rookies are Oskari Muhonen, a Finn sailor from Finland; Jee-min Ha, a Laser Olympian from Korea; and Ricardo Fabini, a Snipe champion from Uruguay. All three are paired with a competitive Star crew from a different country. New boat, new teammate, sometimes ­drastically different native tongues…what could possibly go wrong? Star boats are notoriously difficult to sail, so the class veterans have a definite advantage—even though some of their Olympic medals and gold-star emblems were won before three of these 2019 ­newbies were born.

Haddad is a full-time sailor who represented Brazil at the Rio Olympics in the 470, finishing 23rd of 26 teams. The 470 is a boat he says is “like a drug,” one he genuinely enjoys racing, and while he hopes to compete in the 2020 Tokyo Olympics, a disappointing pre-Olympic result this past summer has led him into racing other boats. “What helped me is that I sailed a lot this year,” he tells me, his brown eyes locked on mine, his smile mixing matter-of-fact with a dose of humility.

In September 2019, he and his teammates finished 13th at the J/70 Worlds, and then shortly thereafter, with only a few weeks of practice, he won the Snipe Worlds. There were plenty of Snipe class legends there too, including Haddad’s Olympic coach, Alexandre Paradeda—the 2001 Snipe World champion—and his Olympic 470 teammate Bruno Bethlem, himself a two-time world champion Snipe skipper. Beating his tuning partners, who he likens to older brothers, was fulfilling, he says. “It means I learned a lot with them, and I have a lot of respect.”

Unlike the other SSL Final rookies, Haddad lives in a ­country rich with Star sailing royalty and traditions. Brazil is home to the supremely talented Grael family (Torben and Lars in the Star, Martine in the 49erFX), as well as the most successful Star crew in the world, Bruno Prada. Haddad says Prada was instrumental in getting him up to speed in the Star, but even after enlisting Boening, who sails out of the same yacht club in Rio de Janeiro, he didn’t think they should even bother to practice ahead of the event in the Bahamas. “Let’s go there and have fun,” he remembers telling Boening, “because I thought it was almost impossible to be ­competitive at my weight.”

For the record, he’s roughly 143 pounds wet.

“The 470 guys who come [to the SSL], they have a lot of ­difficulty,” he says, “but Bruno told me that the races would be inside [Montagu Bay], where it’s going to be shifty. Magilla said I could be competitive, so then I asked him, ‘OK, how many days you can spend with me?’ And he said, ‘About 20.’”

He had his first crack at the Star in November, only a month before the championship, he tells me. He pauses to sip his coffee, unaware that he’s crumbled my misconception that the Bahamian event was his first time in a Star boat. “I did two regattas at my club,” he says, “one with Magilla, and the other with Bruno.”

He reminds me that Rio de Janeiro’s 30-boat Star fleet is revered around the world. “Many guys enjoyed that I had this possibility, so they helped me a lot—sharing and helping me train, and giving me some tips about the boat. The Star fleet in Brazil, it is quite strong.”

Twenty days of practice in the boat is a drop in the bilge ­compared with the experience of Star sailing legends, but it was more than twice what the other three newbies managed—­combined. Without that practice, he says, his performance in Nassau would be “very bad, for sure.”

After three days of racing, however, he says he’s feeling really competitive and understands the boat. Haddad then credits his teammate for much of this new confidence. “Magilla, he has a really good feeling about the boat. He asks me: ‘How is the rudder? How is the pressure on the boat?’ So I tell him, and he is just ­working on that.”

Boening also explains what each change does to the boat. Haddad talks to him a bit about settings or mast rake, but in the end, Haddad has the last word: “I just tell him what I’m feeling.”

The Star is different from any other boat he’s sailed, but he refers to it as a big Snipe. “But [downwind in] a Snipe, when you put the bow up, the boat doesn’t go,” he says, while in the Star, “it helps to go up higher and then quite lower, and so on.” Initially, he also struggled to feel connected to the boat upwind because he had to lengthen his hiking straps so much to compensate for shorter legs.

Nevertheless, he expects that much of what he is learning in Nassau during the League Finals will eventually help him in the 470—and with every other boat too. “It’s really incredible to feel the boat, the pressure, the settings. Many friends say that the Star is the best school because it has a huge main, and that’s true. It is unbelievable how you can feel the pressure and then talk about it, with running backstays in our hands. It’s not easy to keep going fast, but it’s easy to feel when the boat is overpowered or not powered enough.”

Before qualifying for the Finals’ finals, Haddad is confident that he and Boening can remain in the top 10. “Each day I’m feeling better,” he admits. “I hope that tomorrow may be better…that it’s going to be easy.” He smiles to indicate this is more sarcasm.

Easy? Not a chance. Better? Yes. Much better. The young Brazilian skipper and his crew win the first race of the day and finish fifth in the 10-boat quarterfinals. They’re the only newbies to advance to the next round. The breeze drops for the one-race ­semifinals, the lightest conditions of the week, and after struggling with acceleration off the starting line, they finish last—cementing seventh overall. But the top-six teams, collectively, have won a total of nine Olympic medals and 14 world championships. The four finalists all have gold stars on their mainsails, indicating a previous Star world victory.

What is it like sailing against such a legendary lineup? Haddad says he doesn’t think about who he is racing against—at least not while he’s on the water. “Obviously, I ask Magilla where is some guy, but more to know about the course,” he says. “I don’t think, Who is this guy that’s next to us? I’m sailing, just like it was a nice night.”

Ashore, with all the sailors staying at the same hotel, it’s a ­different story. “When we have a breakfast together, or gather after sailing, we realize who we are sailing against,” Haddad says, his gaze wandering across the yacht club’s pool deck. The other teams have already returned to the hotel. “It’s really interesting to have ­breakfast with Hamish Pepper, also Mateusz and the others.”

When asked if he knew many of the legends before arriving here, he shakes his head. “Only the match-racing guys: Taylor Canfield, also Torvar Mirsky and Ian Williams. Oh, and Fabini, from the Snipe. The other guys—no, I didn’t.”

And then, brown eyes locking on me once again, he names an absent Star legend. “To be here with these kind of guys, for me it’s really interesting because my father is one of the best friends of Torben Grael.” Haddad’s father covered the two Olympic Games (1996 and 2004) as a journalist, when Grael won his two Star gold medals. “This is my memory from when I started sailing: It was just after the gold medal of Torben and Marcelo, and my father had just come back from the Olympic Games. So I grew up watching them. To be here, fighting with these guys in the Star class 20 years after, is something that for sure I never expected. Because of my weight, I couldn’t imagine one day to be sailing in Star.”

And though he’s already shattered my misconceptions about his rookie status, something he says makes me certain that Haddad will live up to his nickname in the coming years. “I really enjoy sailing,” he says, eyes twinkling and grin stretching even wider than usual. “I pass almost 24 hours thinking about it, how to make things better and how to make the boat go fast. These days here are helping me a lot. And I’m sure that tomorrow, I’m going to feel even more comfortable than I am today.”

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Thousands of Star class boats are spread around the world, each with a unique personality, and certainly a unique story. It’s true that a boat can eventually reflect the persona of its owner, and this is especially true of the Star boat Gem IX, once the pride of Bahamian legend Sir Durward Knowles.

Gem IX is an appropriate name for this boat, for many reasons. Built by the late great Skip Etchells at the Old Greenwich Boat Co. in 1963, the hull is as stunning today as it was when Etchells sculpted its Port Orford cedar, a light, strong and fine-grained timber milled in the coastal mountains of Oregon. The boat was commissioned and first owned by Knowles, my mentor and dear friend. Knowles and Cecil Cooke won the Gold Medal at the 1964 Olympic Games in Tokyo with Gem IX.

I first met Knowles in 1978, at the Royal Canadian YC in Toronto. I was crewing for another mentor of mine, Thomas David Blackaller. At 18 years old, I was in awe of the Star class and the luminaries who coveted racing this special boat. In crewing for Blackaller, I was immediately competing against Dennis Conner, Buddy Melges, Carl Buchan, Lowell North, Ding Schoonmaker, Pelle Petterson, Joe Duplin and many others. Knowles’ peers were North and Melges, the Gold Star and Gold‑medal winners of the day. He stood out as an island boy, then even at the age of 61. He had an unmistakable relaxed aura, and his accent made him virtually impossible to understand.

RELATED: Inside the Classes: Etchells

After crewing for Blackaller, Bill Gerard and Vince Brun, I eventually began skippering in 1983. A year later, at the Western Hemisphere Championship in Nassau, I won my first Silver Star. At the time, I was a guest in Knowles’ home throughout the event. He would coach me every morning on the wind and current for the day. He was a heavy-air specialist, and I was too, having grown up sailing on San Francisco Bay. Nassau was always windy in April, and he loved that I was winning in his hometown.

I went on to win the Silver Star four times in Nassau over the following 25 years. My crew and I were always house guests of Knowles and his wife, Holly. He and I would sit up late at night, on his porch overlooking Montagu Bay, and he would talk story to me. There was the trailer that broke away from his car in Alabama in 1947, Bahamians who couldn’t drive in the United States, splitting tacks with Dick Sterns and Petterson on the last windward leg at the Tokyo Olympics.

He took me down to the port of Nassau at 4:30 one morning to bring a ship in with him. Once, he drove me to the airport at 5:30, got in a head-on collision returning home and spent two weeks in the hospital. He traveled to San Diego in 1992 to bring advice and support to me in the America’s Cup.

In 2015, Don Parfet and Jon Vandermolen, longtime Star sailors, had a vision to restore 12 wooden Stars as a way to celebrate the history of the class. They decided to organize the first Vintage Gold Cup in 2017, hosted on Gull Lake, Michigan. I was invited as a guest skipper, and knowing my relationship with Knowles, they put me in Gem IX. Knowles was thrilled when I told him about the regatta. After the first day of racing, I called him immediately and shared that we had won two of the three races and were leading the event. I told him I would organize a call with him on FaceTime the following day so he could see the boats. “See da boats?” he asked. “In da phone? No mon, not in da phone!”

I said, “Yes, mon! I will call you tomorrow.”

The next day, I shared the boats and some of the skippers he knew over FaceTime. He was incredulous of it all. Can you imagine a 100-year-old seeing people and boats live through a phone?

The first time I sailed Gem IX, I experienced sensations I’ve never felt in the two dozen other Stars I’ve raced in my 40 years of Star sailing. It was perfectly balanced, which concerned me about pointing, but it proved to be a strength. Fast is high! As a 55-year-old wooden boat, it reacts differently to gusts than a stiff and rigid fiberglass hull; it torques and works its way to windward.

How it feels under sail reminds me of something Knowles used to say when giving me advice on sailing through the chop in Nassau. “Slack da hand, mon,” he used to say. “Let de boat walk.” Knowles was like Gem — relaxed and forgiving, not rigid and stiff.

Knowles stopped racing as the years passed, but I always made time to see him or call him to stay in touch. Sometimes I made special trips to visit him: for his 100th birthday party, and several times during the Star Sailors League event in 2017. But something called me to Nassau in February 2018.

I was in Miami, racing in the Star Masters at the time, so on Monday, after the event, I hopped on a plane and had a lovely lunch with him, Holly and their oldest daughter, Jill, on the very terrace where we’d spent so many nights talking.

The next day, I returned to Miami for the Star Midwinter Series, and Vandermolen said to me, “Paul, you should buy Gem. She’s calling you.”

He was right, so I did. I was excited to be the custodian of such an important part of Star history, to own a boat that was so dear to Knowles.

Two weeks later, his youngest daughter, Charlotte, called me and told me he was in the hospital. I asked if I should fly there. She said he had an infection in his lungs but it seemed to be under control. At 100, it’s hard to shake an infection, even if you are the Sea Wolf. I told Charlotte to tell him that I had bought Gem and that I would take care of her. She said he smiled broadly.

He passed away on February 24, 2018, as the oldest living Olympic champion. He was the pride of the Bahamas, being their first Olympian. He was dedicated to his church, his country and his family. He was an icon far outside of his tiny island nation. I am lucky to have happened into his life, to have him take me under his wing. Gem represents all of this to me.

In September 2018, I introduced Gem IX to its future custodian, my son Danny, a third-generation Star sailor behind his grandfather, Petterson, and me. In a fitting tribute to Knowles, we won the Vintage Gold Cup, Danny got his first gold wreath and Gem IX stands undefeated on Gull Lake. I am certain Sir Durward is smiling, as am I, for the boat is now part of my family, where it will remain long after my time on this planet.

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In Olympic sailing, there’s a pretty good case history of favorites not performing well, and at the 2000 Olympics in Sydney, my crew Magnus Liljedahl and I almost joined those ranks. We went into the Games as the anointed ones in the Star class, at least according to Sports Illustrated. We had won the Star World Championship a few months before the Games, so we were the logical choice.

Growing up around Dennis Conner and working for him, I considered “no excuse to lose” part of the path to winning. I think this approach was one reason I never felt too much pressure on the course — that, and my ability to keep calm, never getting too ­excited or too down. However, there was still a lot at stake for me in Sydney. I’d won a gold medal in 1992 in Barcelona, but there had been missed opportunities as well, some under my control and some not. There was President Carter’s decision to boycott the 1980 Games in the USSR. We were the leading team, but like many, we didn’t sail the trials because of the boycott. Then, when I got my next chance eight years later, in Seoul, a broken mast netted us silver. And the last time I’d been in the Olympics, in 1996 in ­Atlanta, I’d finished eighth.

That wasn’t the way I wanted the story to end, so I entered the 2000 Games with intensity, but true to my Southern ­California ­upbringing, I did so in a laid-back manner. I had the drive to win; I just didn’t wear it on my sleeve.

Magnus was from Sweden — about as far away from Southern California as you can get, and not just geographically. When I first met him in 1979, he had finished second in the Finn Olympic trials, one place away from going to the Olympics. Even thought that was years before our Sydney campaign, I’m sure being that close drove him even harder to make the team this time around. He was well prepared for this competition, as we both were, but his intensity was palpable.

I recall him being taken aback by the fast-food restaurants at the Olympic Village. He pointed at them and told me, “Those shouldn’t be here.” He ate only the right foods, paying close ­attention to calorie count, protein levels and so on. He went to bed at 8:30 every night and rose at 6 a.m. to work out. In a way, he was ahead of his time, because routines and close attention to nutrition are standard for Olympic-level sailors today. Back then, that approach was the exception. On the water, when we did well, he pumped his fists in the air with ­excitement and enthusiasm, and when we didn’t, he used the setback to drive himself even harder. Early in my ­junior sailing days, I went through a period where I would get ­emotional about wins and losses, but over time I ­became almost stoic, so at least outwardly, Magnus and I ­presented quite a contrast.

My success often came from consistency — not trying to win ­every race, but rather having good races and trying not to have bad ones. Sometimes I didn’t win, but I was always near the top, and when the opportunity was there, I took advantage of it and would win. I’ve learned to let other sailors make mistakes and to only get aggressive at the end of a regatta, if necessary. In ­Barcelona we were consistently at the top of the fleet right from the beginning, leading from start to finish. In fact, we didn’t have to sail the last race. That’s rare, but it happens.

Sydney was a different story. On the first day, my tactics were way too aggressive. I was trying too hard to make big gains. In the first race, halfway up the first beat, we were the farthest boat to the right. I was confident it was the place to be, and the Australians were with us — always a good sign. But the wind went left, and at the first mark, we were at the back of the fleet. To add ­insult to injury, we always carried two whisker poles, and whether it was Olympic jitters or not, we managed to drop both of them overboard and ended up crossing the finish line with the jib held out by hand. Between the whisker pole debacle and my tactical blunder, we found ourselves starting the Olympics in 14th. We finished the final race of that day with a third. That helped somewhat, but we knew that first race would be tough to overcome.

It was obvious to our coach, Ed Adams, that we were both trying way too hard. He sat down with me and stressed the importance of returning to the way I’d always sailed — conservatively. That approach had brought me to the Olympics, and if I wanted to do well, that’s what would do it. He reinforced the idea that I had to fight for each place, even if it meant not finishing in the top few positions; I didn’t have to win every race. We continued to struggle for the next two days, and halfway through the regatta, we were sitting eighth overall. Ed also spent time with Magnus, but took a different tack with him. He took Magnus to the Cruising Club and treated him to a burger and a beer, which was a radical departure from his training regimen. Magnus even stayed up a bit later than normal, and I understood that he stopped off for at least ­one ­other beer — maybe more — on his way home. The next day, it was clear he was starting to relax. As for me, I was ready to return to the way I had always sailed. We won the only race sailed that day.

Halfway through the regatta, we were only in eighth place. Anybody watching would have looked at us and said, “Those guys don’t have a chance of medaling.” But we felt otherwise. Each day on the way in, we’d see the Sydney Opera House, which was visible from just about anywhere on the water, and it seemed to speak to us, ­reminding us of the cliché “It’s not over until the fat lady sings.” And at that point, we were convinced she wasn’t even onstage yet.

As the regatta went on, we became more relaxed and went out to race as we’d done so many times before over the previous four years. On Day 5, we were second, fourth and first, while our competitors began to make mistakes, increasing their points, and suddenly we found ourselves set up for the final day with a guaranteed medal; we were tied with the Brits and five points behind Brazil. The only question was who would get which medal.

We were sailing in the ocean just off the Sydney Heads, and there had been a fair amount of current the previous two days, which was keeping the fleet off the line. The wind was moderate, and everyone was more aggressive. With about 20 seconds to go, we realized we were going to be over-early. We were near the pin, so we decided to just go ahead, cross the line, and loop around the pin. We had one boat, Brazil, below us. We were barely able to cross their bow as the gun sounded. We looped around the pin and started on port. We saw that the X flag didn’t drop, indicating someone else hadn’t returned.

We had catching up to do. Our speed was good, but things got even better as we got headed while sailing off on port tack. When we thought we had gained enough, we tacked and could see we had almost the entire fleet below us, with only Canada, who had led us to the right, ahead of us. The left had been better the day before, but this time the right paid off, and we rounded the first mark in second, behind Canada. Of course, we were paying close attention to the positions of the Brits and Brazilians. The Brits were just a few places back, and we only had to beat them to break the tie. The Brazilians were in about eighth, and even though we had at least the five points we needed on them, we still wanted a buffer between the two of us, in case someone in between us was over-early. It was hard to count exactly, but we appeared to have what we needed. However, we knew that a lot could change during the rest of the race. In this regatta, there was no provision for notifying boats that were over-early; you’d find out after the finish.

Up the second beat, the Brits moved into third, but we had a bit of a lead on them. We considered how aggressive we should be in order to catch Canada. It would be nice to have that extra point in case we needed it to beat Brazil, but it would also most likely mean not covering the Brits, and we couldn’t afford to lose them. We had the points we needed on Brazil, so we covered the Brits. We crossed the finish line second. The Brits were third, and we started counting the boats between the Brazilians and us. It looked like we had the points needed. The wild card would be who was over-early and whether they were in between Brazil and us.

Ed couldn’t come up to us until every boat had finished, but when he approached, my first question was “Who was over?” Ed answered, “Brazil.” We breathed a sigh of relief. It turned out that as we’d sailed over Brazil at the start, they’d broken the line. It was lucky we hadn’t risked trying to catch Canada and possibly losing the Brits.

It appeared we had the gold, but there was one more hurdle. The Star class has a weight rule, so we had to weigh in after coming ashore. The tow in was painfully slow. We had learned that Ed always had a reason for everything; we just weren’t always able to figure it out. Sometimes we were towed a longer distance if Ed knew it would be quicker because of the current, wind or waves. This time we figured he must just be running low on fuel. As it turned out, however, Ed knew we’d be weighed as soon as we came ashore, so he kept us sweating in our foul-weather gear to make sure there was no question we’d make weight, even though we’d been very careful to weigh in every morning. We didn’t have a problem. In fact, Magnus said he’d be willing to cut off a body part if necessary.

That night on the steps of the Sydney Opera House, we received our gold medals as the American anthem played and the Stars and Stripes were raised. As I said, I’ve always been able to stay very composed, but not in that moment.

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