Bryson DeChambeau has stared down pressure in majors. He’s battled Rory McIlroy at Augusta National. He’s faced do-or-die putts at Pinehurst No. 2. Yet according to the LIV Golf star himself, his toughest moment didn’t come in a major championship. It went on the sixth playoff hole at Caves Valley, where a missed five-footer still haunts him years later.

During the recent Break 50 episode that aired on October 15, 2025, DeChambeau opened up about this intimate loss. The wound remains fresh. “When I lost to Patrick Cantlay at Caves Valley,” he revealed during the show. “I remember missing a five-footer to win, and it was one of the toughest moments of my career.”

He previously admitted to Tom Brady the depth of that embarrassment. “That was the most embarrassing I’ve ever felt on a golf course,” he confessed. He felt the crowd’s collective gasp when the putt missed.

In the episode, DeChambeau acknowledged this perspective. “Other people have had tougher moments missing, you know, three-footers and putts for major championships and whatnot,” he said. But this one stuck differently. The loss came at Caves Valley, not Augusta. Yet it hurt more because of how close victory felt.

The 2021 BMW Championship stands out as DeChambeau’s most painful defeat. Both players finished regulation at 27-under par, setting a tournament record. They were four shots clear of the field. Then came the playoff—a grueling six-hole battle that tested every ounce of mental fortitude.

DeChambeau had four chances to end it. He missed from six feet on the second playoff hole. Another putt from 17 feet grabbed the left edge but refused to drop on the third. Each miss felt like a dagger.

Finally, on the sixth playoff hole, Patrick Cantlay buried an 18-footer for birdie. DeChambeau’s eight-footer rolled past. The nightmare was complete. Cantlay walked away with $1.71 million and the FedEx Cup lead. DeChambeau left with $1.026 million and a memory he couldn’t shake.

How Bryson DeChambeau’s resilience mindset shaped his comeback

DeChambeau refused to let that playoff define his career. “This isn’t going to define me. I’m not going to let it define me,” he stated firmly during the episode. Instead, he viewed Caves Valley as a learning opportunity. “I’m going to take this, understand what I did wrong, and go. I’m going to get better next time. That’s it. There’s nothing more you can do.”

That mindset shift proved crucial for everything that followed. The next few years brought challenges—a winless 2022, the controversial transition to LIV Golf, and constant questions about his relevance. But DeChambeau kept grinding. He continued to apply the lessons from that painful August night.

His resilience philosophy began showing results in 2023. He captured two LIV Golf titles, including a historic 58 at Greenbrier. He led Crushers GC to the Team Championship. The wins validated his approach to handling failure.

Then came 2024—DeChambeau’s redemption year. He finished runner-up at the PGA Championship, losing to Xander Schauffele by just one stroke. The sting of close calls continued. But something had changed internally.

The U.S. Open at Pinehurst brought the ultimate validation. DeChambeau faced another pressure-packed moment on the 72nd hole. This time, he got up and down from 55 yards out of a bunker. His bunker shot stopped four feet from the hole. The par putt dropped—victory by one stroke over McIlroy.

The mental framework he developed after Caves Valley carried him through. No panic. No collapse. Just execution when it mattered most.

His 2025 LIV Golf season reinforced this growth. DeChambeau earned over $14 million across 13 events. He captured titles in Korea and Michigan. He currently sits 22nd in the world rankings despite limited OWGR opportunities through LIV.

Great golfers aren’t defined by avoiding failure; they’re defined by overcoming it. They’re defined by how they respond to it. DeChambeau transformed his most embarrassing moment into his most outstanding teacher. That missed five-footer at Caves Valley hurt more than any major championship loss. Yet it built the mental armor that carried him to Pinehurst and beyond.