Caeleb Dressel and the Obstacles Awaiting His Olympic Showcase

caeleb dressel
Caeleb Dressel during the 2020 International Swimming League season -- Photo Courtesy: Mine Kasapoglu / ISL

Caeleb Dressel and the Obstacles Awaiting His Olympic Showcase

After winning a record-tying seven gold medals at the 2017 FINA World Championships and then a record-breaking eight total medals at the 2019 version of the meet, Caeleb Dressel had to wait out the pandemic-induced 12-month delay of the Olympic Games, just like everyone else. But in 2021, Dressel gets a shot at taking his signature steamrolling to the Olympic level.

The accomplishments Dressel could reach at this summer’s rescheduled Tokyo Olympics are significant, even if there’s no realistic path for the 24-year-old Floridian to match Michael Phelps’ eight gold medals from the 2008 Beijing Olympics. But seven? That’s definitely a possibility. Dressel enters the Olympic summer as gold medal favorite in the 100 free, 100 fly and 50 free, and he figures to be a key member of the American men’s 400 free relay, men’s 400 medley relay and the newly-added mixed 400 medley relay. He could make an appearance on the U.S. men’s 800 free relay, as well.

The other piece of history Dressel could accomplish is becoming just the third man to win three individual gold medals at one Olympics. The others, of course, are Mark Spitz, who won four events in 1972, and Phelps, who won four events in 2004 and five in 2008. (Nine women have won more than two individual golds at one Games).

But that’s all hypothetical right now. Winning races in real life is a lot different than projecting based on best times and previous accomplishments. And in real life, Dressel will face a series of difficult challenges this July.

1. Caeleb Dressel vs. Kyle Chalmers

This one will be no surprise to anyone who has followed the men’s 100 free over the past four years. In 2016, Kyle Chalmers was just 18 when he shocked the world and came from behind to win Olympic gold in the 100 free. A year later, he missed the World Championships after undergoing heart surgery, and Dressel took advantage. Showing his abilities on the global level for the first time, Dressel swam a 47.17 to win by a massive margin of six tenths.

caeleb dressel, kyle chalmers, 2019 fina world championships

Caeleb Dressel and Kyle Chalmers congratulate each other after the men’s 100 free final at the 2019 FINA World Championships — Photo Courtesy: Becca Wyant

But when Dressel returned to defend his title in 2019, Chalmers was waiting for him. Dressel went out a half-second ahead of his Australian rival, but Chalmers stormed back and almost got back to dead even at the finish. Dressel won gold in 46.96, but Chalmers was right behind in 47.08. Dressel got the American record and improved to third-fastest all-time in the event, and Chalmers moved to sixth all-time.

Chalmers underwent arthroscopic shoulder surgery in November, but the surgery was minor with a prognosis for a quick return to swimming, and he was back in the competition pool in January. When the two reach their inevitable 100 free rematch in Tokyo, even if Dressel takes another shot at Cesar Cielo’s 12-year-old world record (46.91), Chalmers should be right there at the finish.

2. Watch Out for Kristof Milak

At the 2017 Worlds, Hungary’s Kristof Milak took the silver medal behind Dressel in the 100 fly. Two years later, Milak won his first world title in the 200 fly in stunning fashion, smashing Phelps’ decade-old world record and stopping the clock in 1:50.73. Milak was expected to give Dressel a run in the 100 fly, as well, but he finished a disappointing fourth place as Dressel broke the world record in the semifinal and cruised to gold in the final.

Kristof Milak

Kristof Milak at the 2019 FINA World Championships — Photo Courtesy: Patrick B. Kraemer

In Tokyo, don’t expect the same outcome. The 21-year-old Milak will surely present a threat to Dressel’s gold-medal hopes in the two-lap fly race. His performance at the recent European Championships should put fear into his competition. His 200 fly time of 1:51.10 gave him the top three performances in history, and his 50.18 100 fly ranks him as the fourth-fastest performer ever. Like Chalmers in the 100 free, Milak will be churning and chasing after Dressel down the stretch of the 100 fly.

Also worth watching in the 100 fly is Russia’s Andrei Minakov, who took silver at the 2019 World Championships. Minakov, 19, is heading to the United States to swim at Stanford this fall, and he ranks 14th all-time in the 100 fly at 50.83. Teenagers can drop time quickly, but his window of opportunity may not open until the next quadrennium.

3. The Schedule Dilemma

Excelling at the Olympics requires intense training, mental toughness and killer instinct, but balancing a multi-event program requires a friendly schedule. Phelps took advantage of a good lineup in four straight Olympics, while Ryan Lochte had to deal with all three rounds of the 200 back and 200 IM occurring concurrently. At both the 2008 and 2012 Olympics, he had already competed in the 200 back final when he faced off against Phelps in the 200 IM.

Caeleb Dressel of the United States of America (USA) walks in before competing in the men's 50m Freestyle Semifinal during the Swimming events at the Gwangju 2019 FINA World Championships, Gwangju, South Korea, 26 July 2019.

Caeleb Dressel walks out before a race at the 2019 FINA World Championships — Photo Courtesy: Patrick B. Kraemer

This year’s Olympic schedule will definitely present Dressel with some challenges as well. The Tokyo Olympics will feature evening prelims and morning finals over nine days (prelims Saturday, July 24 through Friday, July 30 and finals Sunday, July 25 through Sunday, August 1). If all goes as expected, Dressel would barely compete over the first three days, with just the 400 free relay finals on his schedule prior to the fourth evening of prelims. That’s when he would get his individual program underway with the 100 free.

The potential issues come over the last few days. On July 31, Dressel would likely compete in the 100 fly final, the 50 free semifinals and then as part of the mixed medley relay, and then on August 1, Dressel would have the 50 free final and the men’s medley relay. While that triple would be grueling, he wouldn’t have to swim in three finals in one session as he has at the World Championships. That’s also a major improvement over the version of the Olympic schedule used in from 2004 through 2016, where the 100 fly and 50 free finals were in the same session, with just the women’s 800 free final in between.

How about the 800 free relay? Dressel actually qualified for that relay back in 2017, finishing sixth in the 200 free at U.S. Nationals, but he has never actually swum the relay at Worlds because he already had two rounds of both the 50 free and 100 fly that day. But he could certainly take a shot at the 200 free at Olympic Trials. That event occurs early in the event schedule, before his sprint events. The 800 free relay would fit with Dressel’s Olympic schedule better than his World Championships schedule, with the final scheduled for about 90 minutes after the 100 free semifinal. So maybe he takes a shot and see what happens. Why not?

So if Dressel were to compete in his three individual events and on all four relays, that would be 13 swims total, with 12 of those swims scheduled for a five-day period. Not ideal but certainly manageable.


Since 2016, Dressel has swum in many high-pressure meets, between World Championships, Short Course World Championships, NCAA championships and the ISL, and he’s come up big with marvelous performances on almost every occasion. The only exception was the summer of 2018, when he missed significant time in training after a motorcycle accident. And even when he does break world records and win world titles, he still finds room for improvement.

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Caeleb Dressel (right) with younger sister Sherridon at the 2020 ISL in Budapest — Photo Courtesy: Mine Kasapoglu/ISL

Days after the 2019 World Championships, Dressel said, “There’s certainly a lot of room to improve on that meet. I was happy with it but not completely satisfied.”

Considering the big picture of what he wants to accomplish in swimming, Dressel gave a thoughtful, introspective answer. “I just really want to try to be the best person I can be, and I feel like my swimming as a way to get me there. I just want to inspire some people, maybe just give some people some hope,” he said.

“I’m not satisfied with what I’ve done in the sport as of right now. I want to keep going. I just want to see how far I can push myself in the sport, and I know it’s going to be tough, but I just want to see. Maybe I can conquer a little bit more of my mind and just keep pushing myself for years to come in this and do something special in my own mind, and that’s really just up to me what I consider that to be. I do enjoy the challenge, and swimming certainly does bring that to me.”

Dressel has been to the Olympics before, but 2016 was just a preview. He got to swim with legends like Phelps and Nathan Adrian as part of a gold medal-winning 400 free relay, but he was never in the mix for any individual medals. This time, he will be the preordained star of the Games, with all the cameras zeroed in on him. This will be his chance to inspire some people and push himself to some special accomplishments.

Yes, he will have some serious challenges to manage—competitors like Chalmers and Milak, the schedule of events and, of course, the one-year delay. But this is a special athlete with a learned ability to step up his game when needed. Come Tokyo, expect Caeleb Dressel to be ready.

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2 years ago

Chalmers had only just turned 18 when he won gold in 2016.

2 years ago

Charmers was 18 in Rio, and had a famous
Slow start.. beware the time drop over that front end speed. If Chalmers turns within 0.2 seconds of anyone, it’s all over. Also, don’t rule out Chalmers in 100 Fly- nothing has been said about him entering this event….. just saying…

2 years ago

Until Dressel wins individual gold all else is a sideshow. The pressure and stress of the Olympic 100 Free final is like nothing else in sport. He can do whatever he likes but he knows in his heart that Chalmers has the right stuff and slayed the beast.
The more relevant question in this article is whether Dressel has it. The Americans are masters at pumping up their own in the media. Keep at it, means nothing.

2 years ago
Reply to  Steve

Calling dressel a sideshow is ridiculous.
Sounds like someone is jealous the best
Swimmer in the world is american

2 years ago

Can’t wait!