If you had to tag any golfer unpredictably funny, wouldn’t you think of John Daly? Let us tell you a story to prove the point. Back in 2022, Caleb Pressley, a former UNC walk-on QB, had just joined the Barstool Sports. Then, being a rookie in the line, he was searching for some content to cover and that’s when he thought of Jon Gruden, the former Tampa Bay Buccaneers head coach in the NFL was also at the Barstool Sports. When he went to get some ideas from him at his office, funny-enough, located at the Hooter’s corporate office near Tampa, Florida, he had a surprise waiting for him. 

Asking at the reception, he learned that Jon wasn’t in his office at that time, but Caleb still got a tour of the office. And as he recalls Gruden’s assistant’s words, “They were like ‘This is John Daly’s room.’ And I was like ‘What do you mean John Daly’s room?’” Hidden behind a book shelf that can open like a secret door into what Pressley called “Chronicles of Narnia,” was a small room with just a mattress on the floor and “a little putting thing.” And that’s how Caleb remembers concluding, “I guess John Daly lives in there, in Jon Gruden’s office inside the Hooter’s headquarters.” Surely, they don’t call Daly the Wild Thing for no reason. But this was just one story.

Apparently, Gruden and John did not just become friends over some Hooters beer. They’ve had some adventures. And yet another one has returned from the past to give us some amusing insights into how unpredictable John Daly is, so much so that it can put the former NFL HC into some humorous troubles. This one comes from Jon Gruden himself, sharing a crazy story from the 2008 PODS Championship on the Pardon My Take podcast.

“I was at the Owl’s Nest they call it. I was just having some beers. I was coaching Tampa, relaxing. Lightning bolt… They suspend play… So Daly comes up with his caddie and this rain delay goes on and on and on. And it gets cold, and it’s wet. It appears like the tournament’s over. So the caddie had a couple of cocktails I guess, and he was off. I had Daly’s bib on. I was wearing his bib, we were meeting fans, taking pictures, and the tournament director came back and says, ‘Mr. Daly, you got 15 minutes to get into the position, we’re gonna play four-five more holes before it gets dark. So, we go up and hit balls and Daly looks at me and he says, ‘Well, you’re wearing the bib, let’s go.’ So I carried his bag.

“And I had been in this Hooters Owl Nest drinking a few beers. I had to pee like a rhinoceros. I got this bag, and there’s like 14 Diet Cokes in there. The umbrella thing weighed like a 100 pounds. We’re on like the 16th, I only did it for three holes. I’m at the 16th hole like ‘Do caddies pee on the course?’ I don’t know. ‘Are there bathrooms out here?’ So I had to go pee and then we come up at the 17th hole where the Owl’s Nest was. That was one of the holes we played. And all my friends had stayed around, everybody was gone, there was no fans left. And the friends started going ‘Caddy, Caddy’. I said, ‘I’m going to get ripped for this.’ And sure enough, on the golf channel, they destroyed me for not having any etiquette,” recalled Jon.

When the host asked how Daly shot on those final holes, Gruden had a simple reply, “I don’t know, I was nervous. But I did not get near the green. I just stayed over there by the bag. I didn’t try to go up there and read putts or anything like that.”

As for Gruden, he must have returned to his day job the next day. But surely, Daly is a man who can turn a rain delay into an unforgettable adventure, and John’s story adds to that mythology. But as of recent, the funny stories have turned into concerning ones as the 2-time Major champion continues to struggle with his health.

From laughter to concern: John Daly’s health takes center stage

Daly’s antics have amused fans for decades, but recent events have clouded his name. Daly, 59, declared he will not be attending the PGA Championship due to health issues after undergoing an emergency hand procedure earlier this year, which was his 16th surgery. “Waking up is a win for me,” he disclosed, underscoring the gravity of the situation.

Despite being in remission for four years, Daly’s body has suffered from bladder cancer, which he has been fighting since 2020. He has been playing poorly lately, especially at the Insperity Invitational, where he shot 27 over par. Daly expressed his annoyance at the schedule problem that required him to pick between the PGA Championship and the Regions Tradition, a senior circuit tournament, even though he had a lifetime exemption to the latter.

Resilient by nature, Daly asserted, “I’ve only been dead 11 times,” and compared himself to Lazarus to maintain his resolve to compete. His indomitable spirit and openness about his ailment continue to win him admirers all over the world. Whether it is transforming NFL coaches into caddies or tackling severe health concerns with humor and tenacity, John’s unconventional ways are both inspirational and stories you could share for ages. Since Daly’s next chapter is always unpredictable, fans can only watch in wonder as he continues to manage the challenges that lie ahead.