This guy paid $75,000 to caddie for Tiger Woods — here’s what he learned

December 6, 2019

NEW PROVIDENCE, Bahamas — “The three ‘ups’ to caddying,” Tiger Woods told David Gilbert with a grin early in his pro-am round on Wednesday. “Show up, keep up and shut up.”

Gilbert was in a rare position: a civilian caddying a full round of 18 holes for Tiger Woods. He’d bid $75,000 for the opportunity to do so at Tiger Woods’ annual charity event, Tiger Jam, in Las Vegas earlier this year.

“We like to support the organization and we’ve done so for a few years,” said Gilbert, the founder and CEO of National Funding, a company specializing in small business loans. “Growing up in Orange County (Calif.), Tiger went to Cypress, I went to Esperanza, so I’ve been following him since I was a kid,” Gilbert said. Gilbert played JV golf when Woods competed against his high school. “When I saw this opportunity, I knew it was something I had to do.”

Woods said he took his umbrella and rain gear out of his bag, and resisted the urge to pull any pranks on the caddying rookie. “We played one trick on a gentleman who was being a little mouthy,” Woods told GolfTV. “And so every hole, unbeknownst to him, we put an extra soda can in his golf bag. By the end of it he was like ‘Why am I struggling so bad? My back’s hurting.’ … We just kept throwing soda cans in his golf bag, so by 15, 16 he’s got 16 soda cans in his golf bag.”

Gilbert said the job was hard enough without any soda cans added to the mix. “I’ve gotta say, it was exhausting. I’m impressed with the physical stamina,” he said. He’d been preparing the job with a rigorous routine of diet and exercise. “I dropped 30 pounds this year for this,” he said. “I did actually work out for the last two months to make sure I didn’t collapse. I didn’t want to be that guy.”

Woods’ day-in, day-out caddie Joe LaCava was on hand to walk Gilbert through the paces and prepare him for Woods’ expectations.

“You’d better have a fresh glove ready for the start of every round,” Gilbert says LaCava told him. “He was unbelievable, he’s a great person and he taught me a lot. We had some good jokes between us and I really got some insight into the connection between the two of them.”

Two things surprised Gilbert about Woods’ approach: First, that he makes sure to pick up his tee on every hole. He definitely re-uses the tees, there was a big focus on the tees,” Gilbert said. “I think that’s just a habit, traditional golf.”

Second was Woods’ emphasis on getting the yardage to the front of the green rather than the pin itself. “He always wanted to know where he could be below the hole,” Gilbert said. From there, it was easy.

“Once you’ve got the club selected? Boom. It’s a machine factory,” Gilbert said.

Tiger Woods sits T5 at the halfway point of the Hero World Challenge.
Tiger Woods sits T5 at the halfway point of the Hero World Challenge.
Getty Images

In all, he said, it was a great day to meet two living legends — Woods and LaCava. “That’s a real craft, that’s a dedicated field,” he said. “And for Joe to be hand-picked, to see the camaraderie between them, that was really something.”

He added that Woods was cheery throughout the round, focused on preparing for the event but also making sure Gilbert was enjoying the process. “I think he’s at a good period in his life, he’s had an unbelievable year and he’s at his own event and he’s got a big next week, so he was in good spirits,” Gilbert said.

“People win the lottery every day. How often does something like this come along?”

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