It was only 100 meters. It took less than 50 seconds, 47.02 to be exact. But it changed everything. When Caeleb Dressel touched the wall six-tenths of a second ahead of Kyle Chalmers, the decorated Australian swimmer, in the 100-meter freestyle at the Olympic Games in Tokyo in 2021, he solidified his place at the apex of the sport, writes WWD.

“His legacy is set as one of the greatest, if not the greatest American sprinter in history,” says Rowdy Gaines, the veteran NBC Sports analyst who won his own gold medal in the event at the 1984 Summer Olympics in Los Angeles. “And that’s saying a lot.”

In America, which has dominated swimming on the world stage for generations, the names that transcend the sport, with some notable exceptions (Michael Phelps and Katie Ledecky), have been sprinters who won the 100 free. It requires speed but also strength and superhuman endurance. The start is critical, and so is the turn at the wall. If a swimmer is too long in the turn, it is virtually impossible to make up critical seconds in the second leg of the course.

On land, Dressel, who is 6 feet, 2 inches, can jump more than a meter off the ground. When swimmers are milling around their starting blocks at the top of a race, Dressel can often be spotted executing a series of standing vertical jumps with elevations that rival the jump height of NBA players. That vertical leap, off of a swimming block, is one of Dressel’s defining skills. By the time he surfaces, he’s already ahead of the field.

“It feels like he’s going to pull the block out of the concrete when he takes off on a start,” Gaines adds. “He just destroys his competition.”

Dressel has practiced his start hundreds of thousands of times. Honing his foot placement, his reaction time, the swoop of his 74-inch wingspan. A swimming nerd, he dissects his underwater race videos, filling dozens of spiral-bound notebooks with details from each. But he is also a preternaturally gifted athlete, able to contort his body in the water in ways that seem to defy human limitations. When he is on the starting block, and the arena is still and quiet, the water becomes his destiny.

“There’s nothing there,” he says, closing his eyes. “It’s the quietest place in the world. Once I hear, ‘take your mark,’ everything fades out, everything just goes away.”

“And then actually hitting the water is one of the most special feelings,” he continues, his blue eyes open wide now. “You’re entering a whole new atmosphere. You’re no longer in breathable air. You’re in a very intimidating force of nature that you’re trying to have this dance with.”

Dressel’s gold in the 100 free was his first individual Olympic medal. He would win a total of five gold medals at the Tokyo Olympics—delayed a year and bereft of spectators due to the coronavirus pandemic. (His family watched the Games at one of the many Orlando Studios watch parties set up by Olympic broadcaster NBC.) With subsequent gold medals in the 50-meter freestyle, 100-meter butterfly and the 4×100-meter freestyle and medley relays, he became only the fifth American (after Mark Spitz, Matt Biondi and Phelps and speed skater Eric Heiden) to win five gold medals in a modern Olympic Games. He has two gold medals from the 2016 Rio Olympics, in the 4×100 freestyle and 4×100 medley relays. And he holds world records in the 100-meter butterfly (both the long and short course), the 50-meter freestyle (short course) and the 100-meter individual medley (short course).

His performance in Tokyo made him a star (and earned him endorsement deals with Omega, Speedo, Toyota and Nobull). He will enter the 2024 Paris Summer Olympics, which begin July 26 with a first-of-its-kind opening ceremony along the Seine, as the face of U.S. men’s swimming—and the man to beat.

“There’s so much riding on a moment that comes every four years,” says Dressel, 27, during a recent interview between morning and afternoon practices. “It takes everything. It takes an obsession. It takes every bit of you, every ounce of you to just qualify for the Games.”

Three years later, he still finds it difficult to watch the replay of the Tokyo race or the medal ceremony and post-race interviews with his ecstatic family.

“I have to pause the video as soon as my hand touches the wall so it doesn’t go to the interview with my family because I will cry. It takes me right back to that moment. You have to constantly keep that dial turned down, and when it’s time to race you turn it up. And that’s what comes with the sport. I’m not designed to handle parts of this sport. But I’m working on it.”

For many athletes, the mental challenges of their sport are a hidden—and potentially devastating—opponent. And after Tokyo, the intrusive glare of the spotlight, coupled with years of performing at the highest level, exacted a heavy price on Dressel’s psyche. So in 2022, during the world championships, he stepped away from the sport. “It was blatantly obvious that I needed to get help if I wanted to live a healthy, happy, joyful life,” he admits.

His hiatus stretched on for eight months. He returned to training in February 2023. But that summer, he failed to qualify for the 2023 World Aquatics Championships in Fukuoka, Japan, a stunning fall for the 13-time world champion.

“Some people just have a better skill set to deal with the pressure,” Dressel says. “Quite honestly, mine’s not that great. It’s not something I was born to deal with, which sucks to say, considering that there are millions of people watching the Olympics.”

He’s been seeing a therapist at least once a week for the last two years and also limits his social media engagement, resisting the temptation to doom scroll on his Instagram account, where he has 630,000 followers. “I throw up a post and then get the heck out of there.

“I can handle the physical elements of the sport,” he continues. “The water’s never hurt me. I’ve always had a great relationship with the water. The sport and water are two totally different things.”

A new focus on mental health throughout society has destigmatized an issue that for many has been a lonely and silent struggle. And in recent years, athletes have begun to speak publicly about the pressures and psychological challenges of competition. U.S. gymnast Simone Biles pulled out of the team finals at the Tokyo Games, citing stress. Tennis player Naomi Osaka abruptly withdrew from the 2021 French Open after disclosing her battle with anxiety. And Phelps, who has said his depression began after his first Olympic Games in 2004, struggled publicly for years before getting help, enduring multiple suspensions from governing body USA Swimming for DUI arrests. After his Olympic career he became a celebrity spokesperson for online therapy service Talkspace.

“The mental side of the sport has been the biggest difference for me this year,” says Dressel, “tuning into my mental chatter, welcoming it, whether it be negative or positive. It has helped me deal with pressure and media and outside forces I can’t control.”

Among the many aspects of the sport he can’t control are the internecine issues that have periodically cast a pall over the Olympics. Chief among them, for the athletes and the future of the Games, is the specter of systemic doping. In April, The New York Times reported that 23 Chinese swimmers on the country’s women’s team tested positive for the same powerful performance-enhancing drug months before the Tokyo Olympics. They were allowed to compete after Chinese officials secretly cleared them and the World Anti-Doping Agency responsible for policing the use of banned substances declined to take action. The Chinese women won the team gold in Tokyo, with the U.S. women’s team taking silver.

Russia, meanwhile, has been caught operating a long-running, state-sponsored doping scheme that has resulted in the rescinding of 48 Olympic medals. In 2019, WADA banned the Russian federation from all major sporting events, but the toothless punishment allowed athletes to compete under a neutral flag. And in 2020, the international Court of Arbitration for Sport reduced the ban to two years after Russia mounted an appeal.

“You would like to think that everyone’s doing what you’re doing and it just boils down to hard work,” Dressel says. “But the cheaters are out there. There are people I have raced against who have probably been doping and not been caught. I would like to be able to put more of my trust in the organizations that are supposed to be protecting us,” he says, citing WADA and the Fédération Internationale de Natation (FINA), the world governing body for aquatic sports.

“I’ve never understood how someone can fail a drug test, do their time and come back. If you’ve ever failed a drug test, you should not be able to compete ever again. There’s such a thing as muscle memory when you’re taking illegal drugs. When I’m done swimming, I will be a lot more vocal and active. Right now, it’s not worth my mental energy; I have practice in a couple hours.”

That Dressel may harbor a desire to someday take on a broader advocacy role in the sport is not a surprise to Anthony Nesty, his coach while at the University of Florida and the U.S. men’s team coach for the Paris Olympics.

“People seek him out for advice. At this point in his career he’s been there, seen it all, and to have him around our athletes in that capacity, it’s a big plus for our program,” Nesty says. “The reason we get paid is for performance, but he’s the perfect package. He’s a good kid, he comes from a good family, he’s got a great character, and he’s of course a great athlete. He goes above and beyond to help the person next to him.”

“What he’s done outside the pool with his mental health quest will leave a much bigger legacy in the long run,” Gaines says. “Caeleb is [speaking out] as he’s competing at the highest level. When I was a swimmer, it was suck it up or else because you don’t want to give any of your rivals the least bit of advantage. When you’re talking about mental health and the peaks and valleys that you go through, he has a lot of people pulling for him, that’s for sure.”

Of course, to get to Paris, Dressel first has to qualify at the U.S. Olympic Team Trials, which begin June 15 in Indianapolis, Ind. And this year’s meet is shaping up to be a unique spectacle. For the first time, the trials are being staged at a football stadium, with three temporary pools installed at Lucas Oil Stadium—home of the NFL’s Indianapolis Colts. There are fan activations, music and merchandise pop-ups, all while about 900 swimmers vie for 50 spots—some decided within hundreds of a second—over nine days in front of a 30,000-capacity crowd. Dressel is expected to easily make the team. And how he performs in Paris has the potential to cement his Olympic legacy and bolster his marketability beyond the sport.

For most Olympic athletes, endorsements are a critical stream of income. (There is prize money in swimming, but it’s relatively paltry. Top finishers at the swimming world championships earn $20,000 for each gold medal, with a $30,000 bonus for setting a new world record; the U.S. Olympic and Paralympic Committee only began paying medal winners in 2017—$37,500 for gold, $22,500 for silver and $15,000 for bronze.) Dressel’s partnership with luxury watchmaker Omega (the company’s relationship with the Olympics dates back to 1932) is the brass ring of Olympic endorsements. But even for star athletes in the most popular Olympic sports—swimming, track and field and women’s gymnastics—endorsement opportunities are largely confined to the four-year cycle of the Olympics.

“No one really tunes in except every four years,” Dessel concedes. “That’s just part of the sport.”

Household-name status is conferred on only the most charismatic and decorated athletes. And even when an athlete achieves celebrity cachet, their ability to remain in the public eye can be fleeting.

“The opportunities are few and far between,” Gaines adds. “I hope in the future, our sport will do a better job of helping athletes post-career, because the Olympics is not for the faint of heart. You have to win a gold medal or multiple gold medals and then you have to have the characteristics that will drive you to bigger and better things outside your sport.”

Phelps (the most decorated Olympian ever with 28 Olympic medals, 23 of them gold) and snowboarder Shaun White (who’s post-Olympic career has included a video game franchise, investments in several California ski resorts and an activewear line) are recent outliers among male athletes. In general, women have been more adept at pivoting to fashion and beauty industries. Freestyle skier Eileen Gu—who won three medals at the 2022 Beijing Winter Olympics—has become a sought-after model, making her runway debut with Louis Vuitton resort 2023, and appearing in campaigns for Tiffany & Co. Track and field star Allyson Felix launched her own women’s-targeted footwear line in 2021, after revealing that Nike, her longtime sponsor, cut her endorsement pay by 70% when she became pregnant.

Dressel has the sun-kissed good looks and straight-arrow persona that lends itself to a certain caliber of brand endorsements. In person, he is deferential and polite, peppering conversations with “yes ma’am” and “yes, sir.” Even the copious amount of tattoo ink covering his left arm and right leg has a wholesome vibe: a bald eagle, an alligator (an homage to his alma matter mascot), the black bear native to his home state, an American flag and, on his right forearm, the Olympic rings. He listens to pop-punk (Blink 182, Driveway), and likes to bang away on the drums. But he also has a collection of ukuleles.

He’s cerebral when it comes to the sport, but he also has a sense of humor. And the challenges he’s faced down outside of the pool only enhance his relatability for marketers, says Victoria Brynner, who has brokered numerous celebrity brand deals including between Johnny Depp and Dior and Catherine Deneuve and Louis Vuitton.

Athletes, note Brynner, “are heroic. And because of the physicality of what they do and how much they have to practice in order to be at the top of their field, there’s a certain assumption of purity. In terms of endorsements, the athletes’ values are very important.”

Dressel recently signed a new deal with pet food company Nulo. Caeleb and wife Meghan’s Tabby cat Rems and especially black Labrador Jane feature prominently on their Instagram accounts. (The Nulo campaign also features Biles, sprinter Gabby Thomas, and track and field thrower Ryan Crouser.) There are other deals in the works, and if he wins more gold medals in Paris, he can expect another Olympic-timed endorsement windfall.

Dressel’s earliest memory of being in the water was on his dad’s back. Mike Dressel swam in college as an undergrad at the University of Delaware, relocating to Florida to attend veterinary school at the University of Florida. In the Dressel household, swimming was not pushed onto Caeleb and his three siblings. Rather, in a state known for its beaches, canals and the most backyard pools in America, learning how to swim was a matter of safety. And it became an outlet for four energetic children.

“We had to do a sport,” Dressel says. “That was the family rule.”

Caeleb and his siblings—Tyler, Kaitlyn and Sherridon, now 32, 31 and 25, respectively—all swam on youth teams and Sherridon swam at the University of Florida with her brother. A natural athlete, Caeleb also excelled at flag football and soccer. He earned the sobriquet “rubber leg” because of his talent for sending a soccer ball sailing down the field. He may have taken to swimming early, but it wasn’t without its traumas. “I cried when I first learned butterfly. It was so hard. There’s so much rhythm and timing to it. It was brutal. I was like, when am I ever going to need to do this?”

By the time he was in middle school he had a love-hate relationship with the sport. “I would get to a point where I hated swimming,” he says. “It was boring. It wasn’t really the cool sport. Middle school is brutal and you don’t want to be telling everyone you’re wearing a Speedo.”

Nevertheless, in high school he joined the prestigious Bolles School Sharks swimming club in Jacksonville, although he attended the public high school near his home in Green Cove Springs, Fla., a picturesque suburb on the St. Johns River, about 45 minutes south of Jacksonville. (He first met Meghan at the Bolles swimming club. They married on Valentine’s Day 2021 and this February welcomed a baby boy, August Wilder Dressel.)

I want to swim as long as I can, if I’m still enjoying it. But I also want to be good at it. I don’t want to be getting dead last every meet. I don’t think that’s fair to myself or the sport. I truly believe the water tells you when your time is up.”

His dedication and relentless work ethic led to a slew of records and championships. At the 2011 Junior National Championships he broke the 13-14 national age group record in the 50-meter freestyle; the following year, he bested the 100-yard freestyle record in the 15-16 age group. At the Junior World Championships in Dubai, he broke the 17–18 age group record in the 100-meter free. The previous record holder in the event? Phelps. When he was a freshman at Florida, he was selected All-SEC for 2014-15. He won two national titles as a sophomore. And between his sophomore and junior years, he was swimming at the 2016 Rio Olympics.

“Just to make the [U.S. Olympic] team is a milestone,” he says. “You go to trials, people are crying because they just made the team, people who have missed qualifying are crying. It is such a saturated moment a month out from the Games. And then you make the team, you get your cap with the flag on it and your last name, and you have imposter syndrome because you know there are people who are fast enough to take your spot. I had that feeling in Rio. I was a 19-year-old looking around at Nathan Adrian, [Ryan] Lochte, Phelps, all these huge names. I’m like, ‘What am I doing here?’”

After two Olympics, Dressel no longer feels like an imposter on his sport’s biggest stage. And he’ll arrive in Paris in a much different, healthier, psychic space. He’s hyper competitive, but he’s also gracious and humble. He’s quick with congratulations for rivals and he thrives in a team atmosphere. “I need teammates,” he says. “I would not have made it as long as I have in this sport without them.”

He’s also learned how to be more comfortable in his own skin and enjoy his time away from the pool. He and Meghan live on a farm in Micanopy, Fla., south of Gainesville and a little over an hour from where he grew up. They have five cows (Regina, Gretchen, Bambi, Sookie and Peaches) and eight chickens (“all sweethearts,” Dressel says). The latter provide him with his breakfast: five or six eggs, over medium. Dressel extols Meghan’s cooking: “She’s past the point of me calling her a good cook, she’s an excellent chef.” But he’s somewhat sheepish about the amount of food she has to prepare. “Every time we eat dinner, she’s pretty much cooking for four people,” he says. (When they go to a restaurant, he orders two entrees.)

He spends four hours a day in the pool and another two to three hours in the weight room. He’s out the door in the mornings by 5 a.m. for the first training session, then he returns home, eats his eggs with some bread and fruit and takes a nap. He returns to the gym in the afternoon for weight training and more pool time. It can be a slog, and getting his endorphin high with activities outside of swimming has helped; he has a pickleball court and basketball hoop at his house.

He’s not sure if the Paris Games will be his final Olympics. He would like to compete on American soil in the 2028 Los Angeles Summer Olympics. He’ll be 31 years old at that point.

“I want to swim as long as I can, if I’m still enjoying it. But I also want to be good at it,” he says. “I don’t want to be getting dead last every meet. I don’t think that’s fair to myself or the sport. I truly believe the water tells you when your time is up.”

Whenever that time comes, he would like to stay close to the sport, and muses about someday coaching, the path of many former competitive swimmers. (Nesty won a gold medal in the 100-meter butterfly at the 1988 Olympics in Seoul.) And although he is a student of the sport, he seems to have ruled out becoming an on-air analyst.

“I have trouble sitting still. I have to be moving. I don’t know if I can be up in the booth with Rowdy, I feel like I would explode.”

He also still has trouble watching races—that goes for his own (especially his gold-medal winning 100-meter free in Tokyo) and even races in which he’s not participating. “I feel out of control,” he says. “It’s really tough.”

His mom Christina says her son’s emotions have always been very close to the surface. “He’s emotional at home and he’s emotional in public. But I love that. I think it’s authentic.”

For Dressel, understanding the origins of those emotions, and sitting with inevitable failures, is obviously still a learning process. Maybe the answers are in the water, or maybe it’s somewhere else.

“I don’t see myself being able to step away from the water, or get a job where I don’t get to interact with people on deck, getting to hear the water, smell the water, get splashed by it. I need to be around the water,” he says.

Then he pauses, an idea forming in his head.

“I think right after, like the day after I’m done with my last race, I am going to hike the Appalachian Trail. That’s a good five, six months if I’m keeping a steady pace. And maybe out in the woods, I’ll have an epiphany. I feel like the trail will give me give me some of the answers I’m looking for.”