Winning and losing are part of the game. When you win, you celebrate the victory. When you lose, you celebrate the lesson—or at least that’s how Bryson DeChambeau sees life on the course. With an impressive resume in both the PGA Tour and LIV Golf, it’s no surprise he takes defeat in stride. But there’s one loss that still stings, and maybe always will.

The 2021 BMW Championship at Caves Valley is the nightmare DeChambeau can’t shake. He looked like the winner long before it was over, even tipping his cap to the crowd as he walked up to the 18th green in regulation. He had holed a dramatic 12-foot birdie on the 16th, clenched fist raised, a one-shot lead in hand. But Patrick Cantlay had an answer—a clutch 8-foot par putt that was only the beginning of what would become one of the season’s most memorable duels.

Recently, in a conversation with NFL legend Tom Brady on Break 50, DeChambeau didn’t hesitate when asked which moment he’d take back.“The 2021 Caves Valley against Patrick Cantly,” he said. Recounting that horrifying moment, DeChambeau recalled missing a 5-foot putt that could have closed the door on Cantlay in the six-hole playoff. “That was the most embarrassing I’ve ever felt on a golf course,” DeChambeau admitted. “I thought everybody was kind of behind me and I missed the 5-footer, and everybody was like, oh, and I remember hearing that, feeling that. And it was just the biggest embarrassment that I’ve had on the golf course.”

It wasn’t just any missed putt—it was the missed putt. DeChambeau had been in control all week at Caves Valley, looking like the formidable winner. Even after Cantlay hit into the water on the 17th, DeChambeau couldn’t close it out. That final miss inside 10 feet sealed the deal. “I’m never missing this putt again,”  he swore, with frustration etched into every word.

Indeed, when a win is so close yet slips through your fingers, the sting is hard to forget. But it’s not all heartbreak for DeChambeau, he’s got plenty of incredible stories from his remarkable career, too.

Bryson DeChambeau paid tribute to his father

DeChambeau’s journey back to the top has been nothing short of remarkable. After a few years of doubt and the switch to LIV Golf, many wondered if his best days were behind him. But then came 2024, when he delivered some of his finest golf, including a runner-up finish at the PGA Championship and a breakthrough victory at the U.S. Open at Pinehurst No. 2.

For Bryson, the win was about much more than just a title. It was a way to honor Payne Stewart and give back to his father. During the same interaction with Brady, DeChambeau explained how deeply the victory meant to him. “Going back to the U.S. Open, you couldn’t have written a fairy tale story better than that one for me,” he said. “I mean, getting up and down, looking up, knowing my dad was watching—that was really cool. It gets me emotional every time.”

From watching the 1999 U.S. Open with his father and idolizing Stewart, to winning at the same venue, it truly felt like a dream come true. Bryson proudly showed off his trophy, but it was the emotional celebration after his 72nd putt went in that really stood out. He added, “I just wish he would have seen it.”

From the tough times that still linger in his memory to the unforgettable moments that felt like a dream, Bryson DeChambeau has seen it all. And yet, through it all, this golf star keeps pushing forward, proving that the hustle never stops.