
via Getty
DORAL, FLORIDA – APRIL 04: Captain Bryson Dechambeau of Crushers GC reacts from the first tee during Day One of LIV Golf Miami at Trump National Doral Miami on April 04, 2025 in Doral, Florida. (Photo by Lauren Sopourn/Getty Images

via Getty
DORAL, FLORIDA – APRIL 04: Captain Bryson Dechambeau of Crushers GC reacts from the first tee during Day One of LIV Golf Miami at Trump National Doral Miami on April 04, 2025 in Doral, Florida. (Photo by Lauren Sopourn/Getty Images
What started as a playful, two-week stunt has now spun out of control. Bryson DeChambeau’s ShotCup Challenge: a daring trick-shot contest where he attempted to chip a ping-pong ball from the ground floor of his home into a tiny shot glass on the second floor, had captured the attention of fans worldwide. Completing the nearly impossible shot was one thing, but the stakes were raised even higher for his audience: anyone who entered the challenge’s fan giveaway stood a chance to win a $325,000 Bentley Continental GT. But when he finally landed the shot, instead of celebration, he only had an apology and a promise to offer.
The response was so massive that the giveaway rollout didn’t exactly go to plan. As fans rushed to enter, the system was overwhelmed, leaving many unable to access the site at all. Within three hours, DeChambeau jumped on his Instagram Story saying, “I didn’t expect this. You guys crashed the site! We’re gonna make sure you have a chance to enter. Stay tuned.” And so, he extended the deadline by another 24 hours: “Site will be active shortly, going to extend the entry period until 12 pm CST tomorrow.”
And he stuck to his word. “Giveaway is now back up and live again,” he announced by the next hour. He reiterated his apology to fans for the inconvenience and promised that the website would be up and running again.“Sorry about the technical difficulties, appreciate everyone who showed out to the livestream! Link in bio to enter! We are gonna give this thing away!” he added, emphasizing that this wasn’t a gimmick given how trick-shot looked simple on paper but was almost impossible in practice.
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For days, DeChambeau had been trying to chip a ping-pong ball from the ground floor of his home onto a second-story catwalk, aiming for a tiny red plastic shot glass—basically a target the ball barely fit into. To make it even tougher, he started with just 10 shots on Day 1 and added 10 more attempts each day. By Day 12, he had 120 tries in a single session but managed to land the shot on his 15th try only.
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He had landed the ball a foot or two behind the target. But with just the right amount of backspin, the ball’s momentum shifted. It bounced twice behind the cup before moving closer on the third bounce, and before a fourth bounce could even occur, it dropped cleanly into the shot glass. Bryson DeChambeau had finally completed the challenge. His reaction, captured in the video, was priceless. “NO WAY! ARE YOU KIDDING ME! OH MY GOD,” he immediately shouted, sprinting up the stairs in his home to see the proof. He then confirmed that he would be giving the Bentley away on his Instagram Live on Saturday. “SOMEONE IS GOING TO WIN A BENTLEY TOMORROW,” he shouted, before giving fans more composed instructions on how to enter.
That’s when the buzz intensified. One lucky fan would finally get their Bentley via the giveaway hosted on his Instagram live, with support from the sponsor Underdog Sports. All fans had to do was head to the linked website to enter for a chance to win the luxury car. However, the overwhelming response from fans led to the website crashing, causing a delay in the giveaway.
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Is Bryson DeChambeau the king of fan engagement with his jaw-dropping challenges and giveaways?
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Is Bryson DeChambeau the king of fan engagement with his jaw-dropping challenges and giveaways?