Who’s caddying for Tiger Woods at the Hero World Challenge? Here’s the audacious story of his big break

NASSAU, Bahamas — Rick Rielly, the longtime director of golf at Wilshire Country Club, still remembers the first time Rob McNamara showed up to work for him.

“He was 13 or 14 years old and 80 pounds sopping wet,” he said. “He shows up with a towel, he might’ve had a ball retriever and I had him sit on the bench outside the golf shop until something opened up for a single because the caddie yard was a bit gruff in those days.”

Thirty-five years or so later, McNamara has a single bag for the next four days at the Hero World Challenge – the one and only Tiger Woods.

With Joe LaCava, Woods’s caddie since 2011, having moved on to Patrick Cantlay last year when Woods was sidelined following surgery to his right ankle in April, Woods was in need of a bagman this week – and likely at the PNC Championship and beyond – and turned to his right-hand man in McNamara, who has been one of his closest confidants for more than two decades.

“He’s seen me hit a few shots,” Woods said, underselling the value McNamara has brought to his game since he went without a coach beginning in 2017.

All those years ago, McNamara’s father, who had a thick Irish brogue and lived in the neighborhood, talked his way past the gate at Wilshire, a private club not far from Hollywood, and charmed Rielly into giving his son his start in the game. McNamara was shy with a goofy laugh and a thick head of curly hair, but before long members took a liking to him and he worked his way into the bag room while also developing into a decent stick. He went off to Santa Clara University in Northern California and played on the golf team, graduating as a physics major in 1997, just as Tiger was getting started as a worldbeater. But it was golf not science where McNamara eyed making his mark.

After college, Rielly’s father, Pat, moved into the picture as an important figure in McNamara’s career development. Pat was a former PGA president and director of golf at Annandale Country Club in Pasadena, and hired McNamara as an assistant pro, working in the shop. It wasn’t long before McNamara realized the club pro ranks wasn’t the path for him.

He did a stint at a start-up golf web site but when that company went under, Pat assisted on his next big break. When McNamara showed an interest in working as a sports agent, Pat asked his other son, Mike, who worked at IMG –the sports marketing giant founded by Mark McCormack – to arrange an interview. Pat was a good judge of talent, and McNamara got hired in 2000 as an account manager. Shortly after he moved to Cleveland and started at the firm that represented Arnold Palmer, Annika Sorenstam and Woods, one of the company’s top executives, Alastair Johnston, invited McNamara to his office for a get-to-know meeting. 

“It took only a few minutes for Alastair to explain that in all his years Mr. McCormack had never weighed in on a hire at my level before, but after one short call with Pat that all had changed,” McNamara told Golfweek in 2022. “Pat somehow managed to convince Mark, a power-broker attorney and sports-marketing pioneer, that I was the only possible candidate that could handle the job and that it would be a massive mistake for IMG to miss out on this random ex-college golfer who at 24 years old had little to no experience.”

The curly hair is long gone but McNamara has gone on to become Woods’ right-hand man, with an official title of executive vice president of TGR Ventures.

In his early days at IMG, new media was new and he was a digital native, who helped protect Tiger’s rights.

“None of us knew what it meant, and Rob figured it out,” Mike Rielly said.

He became part of Team Tiger with the likes of Kathy Battaglia and Chris Hubman, later leaving IMG altogether when Woods formed his own company. Outside of Mark Steinberg, who has served as Tiger’s longtime agent, McNamara’s been one of Tiger’s most loyal and longest-tenured associates through thick and thin, a contemporary who speaks the same language and a second set of eyes and ears he depends on. It’s a remarkable trajectory from teenage caddie to being in the inner circle with the greatest golfer of his time in a relationship where the respect goes both ways.

“Seeing Robert on TV today, it’s pretty cool to see a kid who started out being overwhelmed and look where he is today,” Rick Rielly said. “He got his break and he took it.”