Grant Holloway was supposed to roll through the 2025 outdoor season, right? After a dominant indoor season, where he bagged his third national title in the 60m hurdles and added to his already impressive count of five U.S. championships (three indoors, two outdoors), expectations were sky-high. Add that shiny Olympic gold from Paris, and it felt like no one could touch him. So, when the outdoor season kicked off on April 19 at the Tom Jones Memorial Invitational in Gainesville, Florida—his turf—everyone figured it’d be just another Holloway highlight reel. But instead of the usual victory, we got a huge shocker.

In a massive upset, 26-year-old Trey Cunningham—yep, the same guy who snagged silver in the 110m hurdles at the 2022 World Championships—came out of nowhere to defeat Holloway in the 110 m hurdles. Cunningham crossed the line in 13.09 (world lead), just edging out Holloway, who finished in 13.18. Dylan Beard took third in 13.33, and Orlando Bennett rounded out the top four in 13.39.

But here’s the kicker: this was Holloway’s first loss on U.S. soil in the 110m hurdles in 11 years. Remember the last race he lost back in 2014? Back when Grant Holloway was just 16, he had a major wake-up call. It was February 15, 2014, and he was a sophomore at Grassfield High School in Chesapeake, Virginia. During an indoor hurdles race, he was completely outpaced by Isaiah Moore, who ended up winning by a pretty big margin.

Grant, being the competitive guy he is, didn’t take it well. He straight-up admitted, “I’m a sore loser, and I know it.” But here’s the thing—instead of letting that loss drag him down, it lit a fire under him. That defeat pushed him to work harder and get better. However, the biggest loss wasn’t that race—it came at the Tokyo 2020 Olympics, where both fans and the country were left disappointed.

Grant Holloway’s Tokyo Olympics heartbreak

Back when Grant Holloway went into the Tokyo 2020 Olympics as the clear favorite in the men’s 110m hurdles? All spectators expected Holloway to win, yet he ended up finishing with silver instead. Holloway competed at 13.09 seconds during the August 5 event but failed to secure the victory that is a gold medal. Rather, it was Jamaican Hansle Parchment who sent a shockwave with his gold win.

Arriving at the finish line with a time of 13.04 seconds, he shocked everyone. The silver medal-winning performance by Holloway following his series of outstanding victories became a major disappointment for him. But he did prove himself again next time. Three years later, with full energy and determination, Grant Holloway returned to the Olympic stage and did exactly what he was supposed to.

At the Paris 2024 Olympics, he snagged his first Olympic gold in the men’s 110m hurdles, running a blistering 12.99 seconds. This victory was a game-changer, completing his “career Grand Slam” with world championship titles and world records already under his belt. And the U.S. team didn’t stop there—teammate Daniel Roberts grabbed silver with a time of 13.09 seconds. It was the perfect redemption for the U.S. after a medal-less showing in Tokyo, and it firmly cemented Holloway’s place as one of the sport’s all-time greats.