What’s it like to caddie with Tiger Woods? Incredible, but also unexpectedly complicated

Over the years, we’ve heard plenty of players recount the unforgettable sensation of playing golf for the first time alongside Tiger Woods. But what’s it like to caddie alongside him? For one man, it was the opportunity of a lifetime — and then it got a bit complicated.

Two weeks ago, Derrick Payne, who owns and operates a Miami-area golf academy, got a call from his friend and business partner Alex Fernandez. Fernandez had a packed teaching schedule coming up and wanted to know if Payne would caddie for his son Jonah, who was hoping to play in his first event as an 11-year-old. Payne doesn’t often caddie for his students — he doesn’t want to appear to be playing favorites — but helping Fernandez is different.

The nine-hole tournament was scheduled for Saturday, Aug. 15. When the field list came out that Tuesday, one name jumped out at Payne: Charlie Woods. That was cool.

Then on Thursday, the pairings came out: J. FERNANDEZ was listed under the same tee time as C. WOODS. At his academy that afternoon, Payne’s mind started to race. What if Tiger would be there? It wasn’t just that Payne was excited about proximity to a celebrity athlete. Tiger Woods, very simply, had changed his life.

Growing up in a small town on the eastern shore of Maryland, Payne had never picked up a golf club. But he got to college (at the University of Maryland) right around the same time that a red-shirted, black-trousered golfer was starting to make waves on the professional level. Payne and a few of his friends, swept up in Tigermania, started spending time at the golf course — and Payne himself had a real aptitude for the game. He looked into teaching and the rest was history.

“My entire career, you know?” he said. “And not just mine, but you look at a lot of kids that I’ve taught, kids that have gone to college to play golf or just wound up loving the game, I know for a fact it’s the same thing for them.”

Two decades later, Payne, 42, has kept rooting on Woods, though he’d never imagined meeting him. Payne had seen his idol before when he came to town to play events at Doral. But that was like going to the aquarium. This? This would be like being in the tank itself.

(An aside: Let’s take a moment to recognize the first feel-good parenting moment from this story. Rather than swooping in to caddie alongside Woods, Alex Fernandez prioritized his son’s comfort level instead, telling Payne that he thought Jonah would be more at ease with Payne on the bag. Junior golf tournaments can lend themselves to parental horror stories, so it’s always nice to highlight the opposite.)

Game day arrived, and Team Jonah and Team Charlie each arrived at the course. Payne and the elder Woods each approached the 1st tee wearing blue shirts, light shorts and double-strap carry bags. Woods introduced himself. Payne kept his composure enough to say his own name. Then he did his best to focus on Jonah.

“This is his first tournament in this age division,” Payne said of his young boss for the day. “I can only imagine what’s going through his brain.” On the 1st tee, Payne had just one hope for his player: Make contact. That part was a massive success.

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At that moment, Payne realized that he’d been feeling some lingering uncertainty about interacting with Woods.

“There’s a reason people say you don’t want to meet your heroes,” he said. “But it became clear right away that this was the exception to that rule.”

Payne struck up a brief conversation on the 1st hole, asking if the Woodses had played the course — The Ocean Course at The Breakers in Palm Beach — before.

“It was just a little question and I knew I’d be able to tell from his response if, okay, maybe you just don’t want to talk,” Payne said. “But he wasn’t like that. He said they hadn’t played there before either and engaged me with a few questions; he wanted to know where we played out of, things like that. It just made it so much more comfortable.”

After just a few holes, though, walking the fairways alongside Woods started to feel — normal. On some basic level, Payne is used to parents eagerly watching their kids play golf. That’s what Woods was there to do.

“It really just didn’t seem like he was Tiger Woods there,” Payne said. “This was just Tiger, dad.”

So what’s Tiger like as a caddie? Did he say anything memorable? Payne said it wasn’t anything Woods said that stuck out — it was how he acted.

“Look, with what I do, I’m around kids who are playing tournament golf all the time,” Payne said. “We’ve got kids who are 6 years old playing in world championship events. And I’m dead serious when I say that Tiger was the poster child of what I tell my parents to do.

“He let Charlie play. He didn’t get in Charlie’s way. He wasn’t over there arguing about what club Charlie was choosing, he wasn’t lining him up, saying, ‘Hey, let’s do this or that.’ He stayed back, enjoyed it and let him play golf.”

For one thing, Payne was excited by watching Woods parent so responsibly because it gave him all the more reason to believe in the superstar. For another, seeing Woods practice the sort of caddying that Payne preaches was validating. “If Tiger’s doing it, maybe I am saying the right things to parents,” he thought to himself.

Payne insists that striking the right balance is no easy task.

“You see it so often in youth sports but especially in golf, parents trying to live vicariously through their kids. It leads to arguments; we see tears all the time. You see dads working on their sons’ or daughters’ golf swings while they’re walking down the fairway, arguing about decisions on the last par-3. And I’m just like, Let them hit the ball! Go find it! Hit it again until it gets in the hole and then be supportive, say great shot. Great effort.”

Payne was reluctant to expand on the specifics of the conversations he had with Woods, but called the entire day a dream come true.

It’s no secret that Charlie has game; he had beaten a similar field in a tournament a week earlier. This time, to the entire group’s disappointment, the event actually got cut short about halfway through due to lightning (to be rescheduled at a later date).

Still, Payne was ecstatic after the round. Woods had exceeded his expectations, as a friendly co-caddie and as a model father, too. Better yet, Jonah had acquitted himself well. “I was so proud of him because he just played so well,” Payne said. “I don’t mean like, scores, I’m not going to talk about that. But I can’t imagine being 11 and trying to play golf in front of Tiger Woods. It was awesome.”

Before they retreated to the parking lot, Woods happily posed for a photo alongside Payne, the two caddies together.

That’s when things started to get a bit more complex.

Payne posted a few photos of the day on his Instagram page. The one of him and Tiger, for starters, but he was so excited for Jonah, too: he added some of Jonah walking alongside Charlie. With just 600 followers, it never occurred to him that those photos would spread.

“I mean, this was the coolest thing that had ever happened to me,” he said.

But then one of his friends shared an article with him that featured one of the photos he’d posted: Jonah and Charlie walking in front of him and Tiger. Another article popped up. Then another. ESPN. CNN. The Washington Post. The Today Show. Sports blogs. News blogs. He knew there was general curiosity about Tiger’s son’s game, but this?

“Somebody took it off my page,” he said. “I never had that thought of, ‘Wait a second. This might not be something Tiger wants shared publicly.’ I wasn’t intending to show it publicly.

“People kept asking me, ‘Can we have your picture to use?’ I said, ‘No, no, no.’ I didn’t get Tiger’s permission, after all. But it didn’t matter.” The stories were also inaccurate; almost all of them conflated the photos of the day with a different event, on Aug. 9, which Charlie won by five shots at Hammock Creek in Palm City. (Woods was playing in the PGA Championship that day.)

Payne changed his account from public to private, and his page was flooded with new follower requests, some 4,000 or more. He declined them all. He took down the initial post, which included the now-viral photo of the four of them. He reposted just the photo of him and Tiger, expressing his mixed emotions in the caption.

“I want to apologize to Tiger and Charlie for not being more respectful of their privacy. I just wanted to share with my followers how WONDERFUL and down to Earth people you BOTH are,” he wrote.

This was a harsh lesson of the internet; there was no putting this genie back in the bottle. The photo continued to spread. Payne couldn’t sleep.

“It was the best day ever,” he said. “And you know, I felt awful about that part of it. I just teach so many kids, and I’ve been in this game for a while now. The last thing I would ever want to do is have people think I’m trying to exploit someone else’s kids.”

It was hardly the first photo of Woods caddying for Charlie to surface, of course, and it won’t be the last. Highlighting the youngster’s golf accomplishments is hardly negative, and nobody from Woods’s camp said anything to Payne afterward. But he couldn’t shake the feeling that a private moment had gone public outside his control.

“You know, I got to meet my idol in the most intimate settings you could you could possibly imagine,” he said. “It just turned into something else, and I haven’t known how to feel about that.”

Over the course of a recent interview, though, Payne said he was starting to feel better. By talking it out, he felt like he was regaining some control over a story that had far outpaced him. Talking about the joy of the day, he said, was an important reminder just how incredible it was.

If there’s an enduring memory Payne has from the day, it’s the sight of a father watching his son play. And he’s thankful for the photo he got with Woods, too. No matter where else it spread, that one’s going on his wall.