Charlie Woods made headlines earlier this month at the 108th Florida Amateur Championship, impressing many with his poise and potential. The 16-year-old son of Tiger Woods opened with rounds of 74 and 72 at BallenIsles Country Club in Palm Beach Gardens, Florida, making the cut and showing flashes of brilliance. While a tough weekend saw him finish T66 after rounds of 77 and 83, the experience marked another key step in Charlie’s development.

But off the course, another storyline involving Woods Jr. has captured attention—thanks to golf content creator Bob Berger, better known online as Robby Berger or Bobby Fairways of Bob Does Sports. On a recent episode of The Brilliantly Dumb Show, Berger revealed a call he got from Charlie just days before a key qualifier. “Also, I do want to say—we’re at the weigh-ins, me and my dad, and I get a call from Charlie Woods,” Berger began.

“I answer the phone and I’m like, ‘What’s going on, Charlie?’ He goes, ‘Hey Bob, are you free on Monday?’ I said, ‘Well, I’m going to be flying home from New York.’ He goes, ‘Would you be able to caddy for me…’ in whatever qualifier—so I can’t make it in time.” His co-hosts couldn’t believe it! To caddy for Charlie Woods and get a chance to meet the golf legend left the hosts stunned,

Berger continued, “It’s Monday morning at, like… he’s like— I was like, ‘What time is it?’ Monday morning at like 8:00 a.m. So, imagine seeing Charlie… me on the bag. Like, if Tiger sees me on the bag and picks my brain…” Berger clearly sounded regretful about missing the chance, calling the scenario “insane.” Even co-host Mike V. chimed in: “So sick. He would have been like, ‘What? Just do not talk to him about golf.’” After all, who wouldn’t want the chance to walk inside the ropes with Tiger Woods’ son—and maybe even catch the eye of Tiger Woods himself?

While Berger didn’t confirm which qualifier Charlie was referring to, Woods Jr. last played in the Florida Amateur Championship. Earlier in May, he competed in a local U.S. Open qualifier but didn’t advance past that stage. The story has resonated with fans, offering a rare look at the younger Woods’ growing independence and the playful dynamic forming around him. It also highlights how seamlessly Charlie Woods is building his own network and experiences in the golf world, one phone call at a time. Just weeks before this missed opportunity, Charlie made headlines for all the right reasons by delivering the most impressive performance of his young career.

Charlie Woods joined the family legacy with first AJGA title

Charlie Woods officially stepped into the winner’s circle on the American Junior Golf Association (AJGA) circuit, capturing his first title at the prestigious Team TaylorMade Invitational in Bowling Green, Florida, in May of 2025. The 16-year-old surged past the competition with a final-round 66—eight birdies, two bogeys, and a cool composure that mirrored his father’s Sunday swagger. His 15-under-par total earned him a three-shot win and a place in AJGA history alongside his legendary dad.

What makes the victory even more impressive is how quickly Woods Jr. has risen in the junior ranks. Before this win, his best AJGA finish was 25th. But with poise beyond his years, he handled the pressure like a seasoned pro. “Being able to say to myself that I won an absolutely amazing event and to say I performed under some high‑pressure situations is just huge going forward,” he said. “Now I can say I have one, and Dad can’t say I don’t.” Tiger Woods, who won a record-tying eight AJGA titles, now sees his son follow in his footsteps—quite literally.