Some moments stick with you forever. For broadcaster Jimmy Roberts, it’s a 1996 exchange with Tiger Woods that perfectly captured his competitive fire and surprising thoughtfulness. Roberts shared the story with Trey Wingo on January 22.

“I do this long sit-down interview with him. And then I say, Yeah, listen, I got to go. “I’m leaving, you know; I have to go back home,” Roberts explained, remembering their sit-down interview before Tiger Woods’s U.S. Amateur finals appearance.

Tiger Woods didn’t hold back as he playfully told Roberts, “I don’t know, am I crazy, or isn’t it usually customary to stay for the actual competition?”

Roberts had to leave the U.S. Amateur finals early as his wife faced pregnancy complications. Woods won that amateur title. The following week, he turned pro at the Greater Milwaukee Open with the iconic “Hello World” announcement. Roberts showed up among hundreds of media members, and the 15-time major winner’s first words to him showed how thoughtful he actually is.

“Hey, is your wife okay?” Woods asked him, revealing the man behind the competitor.

“I thought that was kind of like this guy’s sharp,” Roberts told Wingo. “It was a very thoughtful thing to say.”

That Milwaukee week proved prophetic.

At the age of 20, Tiger Woods made his professional debut at the Greater Milwaukee Open in 1996 at Brown Deer Park Golf Course. He came in 60th place, which earned him $2,544. The 50-year-old made a hole-in-one on the 14th hole with a 6-iron from 202 yards in the last round. This was his first professional hole-in-one.

Roberts built his reputation on moments like these. He is a well-known NBC Sports and Golf Channel host who is known for his golf coverage and storytelling. He is married to television producer Sandra Mayer and has three sons. Roberts started as a caddie in golf and worked his way up to become one of the sport’s most respected voices. He has a long history of interviewing Woods, including after he won the Masters for the first time in 1997.

One of the most notable moments between the two came in March 2001, following his victory at The Players Championship. A while before this victory, the media had posted the exaggerated narrative that Woods was in a slump. He had gone winless in 8 events from late 2000. So, when Roberts asked what winning The PLAYERS meant to him, a serious-faced Woods replied, “It means my slump’s over.”

Now, their professional relationship has evolved into mutual respect. Roberts once told SBNation in 2013 that Tiger was “playing as well as I’ve ever seen him play,” praising his all-around game before that year’s Masters.

Fast forward to now, the guy who has won it all has lingered with injuries, keeping him off the green for more than a year. The fandom believes he could play in the PGA Tour Champions next, as soon as in May.

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When will Tiger Woods tee it up?

Fans are more curious than ever about when or if Tiger Woods will show up on the PGA Tour Champions after he turns 50 on December 30, 2025. Tommy Gainey has a theory.

Gainey told SiriusXM PGA Tour Radio’s Gravy & The Sleeze that he thinks Woods will tee it up as early as May. He noticed the Insperity logo on Woods’ sleeve. This is the deal: Insperity is the sponsor of a Champions Tour event in Texas from May 8 to 10.

“He signed a deal with Insperity. You could see it on his sleeve, so that’s good news,” Gainey explained. “I will let people think maybe what they want to think on that, but that tells me that if he’s able to play, he’s going to play in that one.”

That statement has a big “if,” though.

In October 2025, Woods had his seventh back surgery. In March, while training, he also tore his Achilles tendon. He couldn’t play on the PGA Tour in 2025 because of those injuries. He said in December at the Hero World Challenge that he had just been given the green light to chip and putt, which meant he wasn’t quite ready for the tournament. He even missed TGL action in January, and he hasn’t said for sure whether he’ll play in Champions Tour events.