Caeleb Dressel was left in tears on Friday night after failing to defend his Tokyo Olympic gold medals in both of the individual events he’d qualified for in Paris.

The Florida native, who turns 28 next month, finished sixth in the 50m freestyle final before coming in 13th in the 100m butterfly semi-finals after winning gold in both events three years ago in Tokyo. After finishing both races within the span of roughly 40 minutes, Dressel could be seen in tears off to the side of the pool, embracing a member of Team USA’s swimming staff.

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“It was very obviously not my best work,” Dressel said. “But the racing has been really fun here. Walking out for the 50 and the 100 fly, it was special. I don’t want to ever forget that. I’d like to be quicker, obviously. Not my week, that’s all right.

“I’d like to be performing better, but I’m not. I trained to go faster than the times I’m going. I know that. So, yeah. It’s tough, a little heartbreaking. A little heartbreaking for sure.”

The road to Dressel’s third Olympics has been anything but straightforward. In 2022, less than a year after his five-gold breakout in Tokyo, he withdrew in the middle of the world championships and took eight months away from the pool to address his mental health.

When he returned at the next year’s US national championships, Dressel didn’t come anywhere close to qualifying for worlds, failing to make the A-final in either sprint freestyle race.

Having been deemed the successor to Michael Phelps since racking up a record-tying seven golds at the 2017 world championships, Dressel admitted to struggling with the weight of expectations. “I get it, trying to find the next guy,” Dressel said at last month’s US Olympic trials. “But I have said multiple times I’m not Michael, at all, and I’m fine with admitting that. I think I’m pretty damn good at what I do. And I’ve exceeded a lot of my expectations in the sport, and I have drained the talent that I have, and I’m still continuing to do that.”

Australia’s Cameron McEvoy took gold in the 50m free, becoming the first Australian man to win gold at these Olympics.

It’s hasn’t all been bad for Dressel. On Saturday, he anchored the Americans to a third consecutive 4x100m freestyle title on the opening night of the swimming program to win his eighth medal at the Summer Games, all of them gold, extending one of the great records in Olympic history.

Only two other men or women, Usain Bolt and Ray Ewry, have won as many Olympic medals without any silver or bronze.

Earlier on a gruelling Friday, Dressel raced for Team USA in the mixed 4x100-meter medley relay heats. That will give him another shot at his ninth career Olympic gold when the final goes off on Saturday night in the west Paris suburbs.

Australia’s Kaylee McCown chased down Regan Smith of the United States to win the 100m backstroke in a time of 2min 3.73min, breaking Missy Franklin’s 12-year-old Olympic record set at the London Games.

Smith touched in 2min 4.26sec for the fifth silver medal of her career, to go along with a single bronze.

“If I had gotten a silver medal and I had been a second slower, I think I would have been really disappointed in myself because that wasn’t putting my best foot forward. That wasn’t what I was capable of doing,” Smith said. “That’s one of my fastest times ever. I think I really gave Kaylee a run for it and I made things really close and exciting. So I’m thrilled with it.”