Triathlete Flora Duffy holds Bermuda's undivided attention heading into Tokyo Olympics

Triathlete Flora Duffy is hoping to represent Bermuda at the Olympics for the fourth time next summer. Mike Stocker for ESPN

WEARING RAIN GEAR and a fading smile, Flora Duffy stood near the finish line and cheered as her friends and rivals approached. The most celebrated athlete on the island was about to conclude her long April day by ending her reign as champion.

Duffy reluctantly withdrew from the 2019 ITU World Triathlon Bermuda because of a foot injury sustained a year ago. Although she was disappointed to let down her home country, she knew it was the right decision to help her achieve her goal of winning an Olympic medal next summer.

Instead of defending her title, she participated in an exhibition relay race that morning. Thousands of Bermudians -- from "little, old grannies sitting in their Bermuda Day parade chairs" to young men smoking joints -- showed up bright and early to support the local hero who had returned home for the event.

Two men standing on the top of a hill made sure she knew they understood her decision. "We still love you, Flora," they shouted, joints in hand, as she whizzed past on her bicycle.

It was a fraction of the scene from a year ago, when it seemed that almost every one of the island's 65,000 residents lined Front Street in Hamilton with their flags and "Go Flora Go!" signs. That day, as Duffy closed in on the finish line, she was so far ahead that she was able to savor every step and take in every familiar face and place in the island's capital, known simply as "town" by locals.

"People freaked out," Duffy said. "There were all these people who I never would have picked out to watch a triathlon. It was so special."

But this year, after American Katie Zaferes crossed the finish line a minute and 41 seconds ahead of the rest of the field, a woman approached Duffy.

"Wow, what an amazing finish," she said flippantly. "How much did you win by last year? Less than that, right?"

Duffy turned to her husband and quietly asked for their hotel key. She pulled her baseball cap over her face, pushed her way through the fans and walked away as quickly, and discreetly, as possible.

Remember the pressure on LeBron James to bring home the Larry O'Brien trophy while he was in Cleveland? That's similar to what Duffy is dealing with -- except she gets one shot every four years, and it's her burden and hers alone.

Duffy has been Bermuda's greatest hope on the world's biggest athletic stage since she made her Olympic debut in 2008. The 31-year-old has won multiple world triathlon championships and is a former world No. 1. Now the clock is ticking toward what she says will be her final Olympics next summer in Tokyo. Bermuda's hopes that she can win its second Olympic medal -- the winner of the first has called himself the island's "dirty little secret" -- seem to grow by the day, even when she's sidelined with injury.

Duffy plans to make her long-awaited return to competition this week at the Olympic test event in Tokyo. The weight of Bermuda's hopes will follow. She doesn't need anyone to remind her of her goals -- or that time is running out.

"It would be huge to get a medal," she said. "Not just for me but for this island."

FLORA DUFFY IS not how you envision one of the best athletes in the world -- nor, for that matter, the face of Bermuda or a recipient of the Officer of the Order of the British Empire (OBE) from Queen Elizabeth herself. At 5-foot-5, Duffy is small in stature, with an unassuming demeanor and a tough-to-place accent that reflects all the places she has lived. She's serious and focused during races but happy to discuss trashy reality television anytime, including her new favorite, "Very Cavallari." She feels the same way you probably do about Jay Cutler. "He's the reality star none of us knew we needed," she says with a big laugh.

Duffy didn't see herself as a future Olympian when she signed up for her first triathlon as a 7-year-old, but then again, she wasn't even sure what the sport was.

"I was in a swim club, and I ran in primary school in the running club," she said over breakfast the day after the 2019 Bermuda race. "I remember thinking, 'Well, I know how to ride a bike. How hard could this be?' And I can't remember if it was me or my parents that found the triathlon, but off I went, and I raced on my old mountain bike with this big foam helmet. I loved it instantly."

Duffy spent her Saturday mornings at Clearwater Beach, a former American military base, training with Tri-Hedz, a newly formed triathlon club. It didn't take long for everyone involved to realize how gifted she was. There were several races scheduled throughout the summers, and Duffy almost always won her age group. She made friends with the other kids in the group and loved the intricacies of the sport, but mostly she had fun with it.

In fact, it was almost an escape for her. As well as participating in track at her school, she was a member of the national swim team, something she said dominated her life. She traveled to the Caribbean on several occasions to compete for the team.

"I remember once when Flora was probably 14," said Steve Burgess, her first running coach. "It's pouring rain outside -- torrential. Rain that you would think of in the Amazon jungle. I'm sitting in my office, and I see her run out of her mom's car, and she looks in the window. She yelled, 'He's in there. Training is on!' and her mom zooms off. I'm thinking, 'She really wants to train in this?' When I realized she was serious, I went out, and we had our normal training session, and she's doing everything like it's not flooding all around us. I didn't know exactly where she was going to go from that point in terms of athletic success, but I knew she was something special."

At 16, Duffy opted to go to boarding school in England. She chose Mount Kelley, in the English countryside, for its strong triathlon and swim programs. She wanted to see how she would compare on a bigger stage.

"The buildings were something straight out of Harry Potter," she said. "We had to wear a long kilt to our ankles and blazers as uniforms and go to chapel every day. The island culture is so different. Even the way I wore my hair made me feel like I stood out. Now I'm fine with being different, but when you're that age, you just want to fit in and be normal."

Thanks to triathlon, Duffy didn't feel like an outcast for long. Competing in a country-wide series for juniors, she placed in the top three in her first several races. Her doubts about being good only by Bermuda standards were erased, and she knew she could compete with the best in the world.

That confidence was tested at the 2005 Junior World Championships, in which she finished in 39th place. During her final year of boarding school, she began her training at 5:30 a.m. and had multiple workouts every day between classes and studying. She went back to the competition the next year and finished second.

With British parents who hold citizenship, Duffy was offered the opportunity to compete for Great Britain and train with its federation in world-class facilities. But she wanted to compete for the only place she considered home and the place that developed her love for the sport. The financial assistance she received from Bermuda at first was minimal compared to what she would have received from Great Britain. Bermuda reimbursed her for travel and entry fees for just six races a year. She was fortunate that her parents could front the rest of the money.

"Getting lapped at the Olympics is a pretty tough thing, and it made me question everything." Flora Duffy

Bermudian officials were unsure if a then-17-year-old Duffy would be able to hold her own at the 2006 Commonwealth Games because she had little experience competing at the Olympic distance, which is a 1.5-kilometer swim, 40-kilometer bike and 10-kilometer run. So they made her do a qualifying race during practice with her coach in England. She needed to complete the course in 2 hours, 20 minutes. She did it in 2 hours, 12 minutes, and she was off to Melbourne, Australia, during her school break to compete against women she still describes as her idols.

It was her first race against elite athletes, and she was the youngest in the field. She finished in eighth place, in 2 hours, 35 seconds. She put the world on notice.

"I was expecting people to be like, 'Is this little Bermuda girl supposed to be here?' But instead everyone was like, 'Who's this, and where did you come from?'" Duffy said. "It was freaky. It went amazingly well. And then I went back to England to finish school."

After graduation, she competed regularly on the elite scene around the globe and notched two top-10 finishes in World Cup events. She was named Bermuda's Young Athlete of the Year in 2006, just months after her 18th birthday.

She made her Olympic debut in Beijing in 2008 as one of six athletes representing Bermuda. She felt run down and fatigued entering the race and was lapped during the bike. Duffy recorded a rare DNF (did not finish). She left China dejected, broken and uncertain.

"It was just a disaster," she said, the hurt still apparent in her voice. "I just felt like I'd hit rock-bottom. ... Between that 18 and 20 age, your body changes a lot, you go through a lot, and for me, I was in this spotlight and had to race at this high level, and I just didn't know how to deal with that.

"I was like, 'I can't do this anymore.' I didn't want to race again. Getting lapped at the Olympics is a pretty tough thing, and it made me question everything."

ALONE IN A tiny touristy store in the basement of a Bermuda hotel, Flora Duffy sat at the cash register. She was 21 and a has-been. She had no pressure, no strict training regimen -- and no window. The lingering smell of mold in the building was more consistent than customers.

She had quit triathlon and picked up the "Twilight" series, along with selling the occasional novelty T-shirt. For months, she read, and sat, and didn't think much about what might have been. But after Bella became a vampire and went off to start her eternal life with Edward, Duffy realized that she, too, was ready for a new beginning.

In January 2009, she enrolled at the University of Colorado Boulder, a school she picked because it had a triathlon program that she could join if she wanted. Instead, she joined a sorority and embraced life as an anonymous college student. She lived in the dorms and went to Lake Havasu in Arizona on spring break.

She joined the cycling team to stay in shape and make friends. She took the competitions seriously, but she found the atmosphere more relaxed than what she was used to. For the first time in a long time, she was happy. But she found herself reluctantly missing triathlon.

After her first semester, Duffy stayed in Boulder for the summer. She started swimming again and cycling with a group every week, and then she started working with a coach.

"It happened organically," she said. "Classes were over, so I had more time. I liked being back in a training routine, but it wasn't at the expense of my social life. It wasn't me going to bed at 9 p.m. and getting my 10 hours of sleep and blah, blah, blah. I still had this other life where I hung out with my friends and went to parties and burned the candles at both ends. I didn't really care too much if I had bad workout. It was just a great balance."

But it wasn't for her. Not for long.

By 2010, she had left the sorority and joined Colorado's triathlon team. That June, after two years away, she entered a World Cup race in Des Moines, Iowa, and finished 20th against the best in the world. She was back.

It was during that 2010 summer training in Boulder that Duffy met her husband, Dan Hugo. The South African triathlete was competing on the XTERRA tour and knew right away who Duffy was and what she had accomplished. He was impressed, if not slightly intimidated, and the two were friendly for several years before they started dating.

Hugo watched in awe as Duffy notched several top-10 finishes and claimed her first victory in 2011 at the Mazatlan ITU Pan American Cup.

"It was clear right away that she was gifted with this incredible engine and has an amazing work ethic, but what really stood out was how she was able to respond and react in challenging situations," he said. "She just is able to rise in those moments and stay calm and focused and execute what she needs to do."

Hugo's words didn't ring true in London, where Duffy returned for the 2012 Games. As part of Bermuda's eight-athlete contingent and among the triathletes to watch, Duffy finished in 45th place. She was within striking distance after a sluggish swim, but she crashed at the start of the bike leg. Her highlight? Carrying Bermuda's flag at the closing ceremonies.

Unlike after Beijing, this time Duffy was determined to improve. Within a few years, she was considered among the world's best. Hugo retired from competition in 2015 and essentially became operational manager for Team Flora, doing everything behind the scenes to ensure that Duffy could focus on training and competition. The partnership has worked. Duffy was the 2016 and 2017 ITU World Triathlon Series champion, the 2015 and 2016 ITU Cross Triathlon World Champion and the champion of four straight (2014-2017) XTERRA world championships.

"I just kept thinking, 'Me? I'm doing this?'" she said. "I had such a happy-go-lucky attitude about it. I was so excited to be racing like that. I had never been a favorite before, and it felt like I was accidentally in that position, which was nice and less pressure than if I had always been in that spot."

She knew she was considered a contender for an Olympic medal in Rio in 2016 but says she didn't think too much about it. What she didn't know until later was how many Bermudians were watching her from home and cheering her on. There was a viewing party at Docksiders, a popular bar in Hamilton, and hundreds came out to watch her compete on the small screen.

But a medal eluded her again. She was among the leaders during the swim and the bike, but she fell behind during the run. She finished in eighth place, 2 minutes, 9 seconds behind gold medalist Gwen Jorgensen and 1 minute, 25 seconds out of medal contention. Bermuda's 40-year Olympic drought continued.

"I came back after the Rio Olympics, and so many people told me, they were like, 'Flora, there wasn't a car on the road when you raced. Everyone was sitting in front of their TVs watching you.'"

CLARENCE HILL WAS 25 years old when he won a bronze medal for Bermuda in boxing's heavyweight division at the 1976 Montreal Olympics.

In the Olympics in which Sugar Ray Leonard struck gold for the United States and in the year when "Rocky" ruled the box office, Hill became the first athlete representing Bermuda to win a medal.

Hill, who is black, returned to an island in the midst of racial strife that had been centuries in the making.

"I felt on top of the world," Hill told the Royal Gazette, the island's only daily newspaper, in 2016. "But then I came home, and the hype and the high dropped because I wasn't represented in my own country. To this day, I don't feel represented in my own country, and I still don't get the credit I deserve."

Bermuda is a small place with big ambition. Its natural beauty and financial wealth sometimes mask the ugliness of racial tension and inequality. Sitting 22 miles long and about a mile across in the middle of the Atlantic Ocean, Bermuda is closer to North Carolina than the islands of the Caribbean. It is 665 miles from the next-closest piece of land.

Spanish explorer Juan de Bermudez discovered the island in 1505 on his way back from Hispaniola, and it was used by sailors as a stopping point during their travels to the new world. In 1609, a British boat called the Sea Venture, destined for Jamestown, Virginia, shipwrecked near the island, and the first settlement was formed. The British claimed the island as their own, and it has remained part of the British Empire since, despite occasional talks of independence.

Much like in Virginia, slaves from Africa helped develop the new territory. The United Kingdom abolished slavery in 1833; Bermuda freed its slaves in 1834, but systematic inequality persisted. Bermuda was desegregated in 1959, but racial strife remained. In 1973, the (white) governor, Sir Richard Sharples, appointed to represent the British monarchy on the island, was assassinated by a man who was a member of a radical black power group. That man was sentenced to death in April 1976, months before Hill's triumph in Montreal.

The governor's assailant, along with another black man found guilty of other killings, was hung in 1977 in the last execution in any British territory. It resulted in violent protests and widespread unrest. Although race relations have improved in the four decades since, the island (in which 54% of the population identified as black and 31% as white in the 2010 census) still has problems.

It was a precarious place for Hill to return to, although he has publicly dismissed the role of race in regard to his reception. He has struggled with a drug addiction and homelessness over the years and spent time in prison for robbery. There have been conversations by those in the community about honoring him in a formal way, but nothing has come to fruition.

"Bermuda has stuck me in a corner and put a blanket over me," Hill said recently. "They don't want people to see who's there. I should be shining. After all, I did something special for my country."

Plans were unveiled in 2017 to name a boxing gym in Hill's honor, but it has yet to open.

In contrast, pictures of Duffy, a white Bermudian born to British parents who participates in a sport that is overwhelmingly white, line the walls of storefronts, the sides of buildings and even the desks at customs in the island's airport. When Duffy is back home, Bermudians of all demographics approach her with open arms. She seems to transcend all boundaries. Duffy has never met Hill; she had never even heard of him when she was a kid.

"It seems like because a few of his life choices, he never got the recognition and stuff he should have," she said. "There are no statues of him or anything like that anywhere, and it's never been, 'Whoa, there's our one Olympic medalist!' Especially when you see how everyone is with me now, it's just strange and very different."

When asked if Hill's status adds pressure to her quest to win an Olympic medal, Duffy didn't hesitate.

"Yes. It feels like everyone wants to have someone we're really proud of."

IT WAS THE day after the race, the race she couldn't compete in, and Duffy wanted to show her husband Admiralty House, a small park on the island's north shore with spectacular turquoise water, a small inlet beach protected from waves, underground tunnels, limestone cliffs -- perfect for jumping -- and a cave with the most Instagram-worthy view.

Hugo and Duffy have been together for six years and married since 2017, but Hugo estimates that he has spent fewer than 30 nights on the island. Duffy can't train here because it lacks elite facilities, so they split their time between Boulder and his hometown of Stellenbosch, South Africa.

"I was born in South Africa during apartheid and saw it end as a child," Hugo said. "As a result, I will never not see color. It is the environment in which I was raised. I know Bermuda has had its issues with this as well, so it's amazing to see Flora be a person that unites everyone."

A young black girl rushed out of the water and up the dock, excitement building with every step. She wanted to take a photo with Duffy. Next came a white couple from California whose son had recently moved to the island. He had told them all about Bermuda's famed Olympian. (Now, they didn't know what sport she competes in, but they recognized the name). A boat, complete with a cooler filled with rosé and rum, pulled up with a gregarious family. It turned out Duffy knows the captain's son.

Many celebrities have that quality that makes fans feel as if they know them, but with Duffy in Bermuda, they usually have some connection. And if Duffy doesn't actually remember running cross-country with someone's granddaughter in 1999 or going to primary school with someone's brother, she hides it well. She handles every encounter like she's seeing an old friend ("I just say, 'Oh, of course!' when they say who they are."). Sometimes when she notices someone staring at her, she preempts any hesitation they might have with a greeting and a smile.

After Duffy won the Bermuda race in 2018, airport officials, fearing she would cause a stir, hid her in a room reserved for high-ranking political figures while she waited for her flight to Colorado. It was a relief for her to land for her connection in Philadelphia and blend in as she made her way through the terminal.

As Duffy and Hugo headed over to jump off the cliffs, the family on the boat offered to take a photographer out on the water for a better view for pictures. "Anything for Flora," they insisted before listing all of her accomplishments and offering snacks and beverages.

On top of the cliff, Duffy stood on the edge and looked down. She bent her knees as if to jump, but it was almost like she needed to convince herself first. It was an obvious sign, one of the boaters pointed out, that she doesn't spend as much time on the island as she once did. After a few moments, she took the 30-some-foot plunge into the water. A few other triathletes, who also happened to be at the park, watched as she jumped. They all followed.

Duffy climbed up the rocks and jumped again. They all did. Everyone else watched in awe. "That's Flora," another young girl said breathlessly.

It's these interactions and these moments that remind Duffy of just how much she means to the island and how much it means to her. While her own ambitions are enough to fuel her to Tokyo, she knows it's about more than herself when she competes with "BER" across her chest. A medal would make every sacrifice, every missed holiday and family wedding, worthwhile.

"It's kind of weird when you get to a level where it's actually possible," Duffy said. "I don't know what it would be like if I actually won one. Everyone seems to feel like they have a connection to me and helped produce this. And it's true in a way -- they have."