Four Hackers and Caddie Named Bobby

Learn How Caddy Time Can Improve Your Golf Score!

Download on iOS Download on Android
Single Golfer With Caddie Bobby at Medalist Golf Club

Four Golfers With Caddie Bobby at Medalist Golf Club

Four Hackers and Bobby

It was the summer of 2009, and I was approached by my boss to ask if I’d like to fly into Orlando and drive over to Hobe Sound to play golf at Medalist. Now I was just a guy shanking a hundred on any 18 back then, but I did know that, with only a year of golf under my belt, I was going somewhere most would never have a chance to go. I also knew that this was happening on my birthday.

And what a day! We saw Jesper Parnevik, we saw all the amazing animals, either land or sea, that Greg Norman hunted, we sat in the same chair Tiger sat in, and we even wore the famous hat worn by the Shark himself.

“Oh man, what’s this guy gonna think when he sees us worm burning and hosel rocketing the ball all day”

Most all of it was overshadowed by our first experience with a caddie though. Here we are, four guys having a complete stranger following us around all day. We were told we had to have one since we were not members. We had won a charity event, so our trip was free; we weren’t too worried about the rest. Well, that was before we got to the range and met Bobby. He had coolers with water, wet towels, and already had yardages for all pins. Suddenly our whole conversation turns to “Oh man, what’s this guy gonna think when he sees us worm burning and hosel rocketing the ball all day.” We were wrong.

Bobby was OUR caddie. He made it clear that his only intent was to make our round more relaxing and fun. We were amazed at how he always seemed to be standing beside each of us when it was our turn to hit. If we were in the bunker, he was there, rake in one hand and wet towel in the other for our club. He had yardages for the ones hitting and the ones waiting. As we would spot our balls on the greens, there he was holding all our clubs, handing us cleaned balls back, and showing us the break, the run of the grain, and making the final shot of each hole more confident than ever. It was truly a game-changing experience.

Towards the end, we asked him if we could buy him a beer, but he stated, “I’d love that, but caddies aren’t allowed inside.” So we all took a picture, hugged, and thanked him for a forever memory.

“Thank you Bobby! Cheers!”

Looking back, our only regret was not having that beer with him. Since then, I’ve had many caddies, all unique in their own way, all allowing the game to be played as it should, and all leaving different, but great, memories and reminders of just how no strangers exist on the grass and no game has ever been so greatly paired as that of an 18-hole round with a caddie.

— Chris Ray, Tennessee

What People Are Saying

What Makes Us Different

  • On-Demand Talent

    Access a network of vetted, reliable caddies with just a few taps.

  • Frictionless Experience

    For golfers, caddies, and courses — our UX works for all users, not just one.

  • Zero Overhead for Courses

    Courses offer full-service caddie programs without hiring, training, or managing.

Recent News & Announcements

Stay up-to-date with what's happening at Caddy Time.

Greg Norman partners with Caddy Time
Greg Norman Joins Caddy Time

“Partnering with Caddy Time isn’t just about business; it’s about my passion for golf, innovation, legacy, and moving the game forward. I’ve dedicated my career to pushing boundaries both on and off the golf course.”

GolfPairs and Caddy Time partnership
New Partnership with GolfPairs.com

We’re thrilled to announce a new partnership between golfpairs.com and Caddy Time, bringing together the ultimate golfing experience with the most advanced caddy-on-demand platform.

Caddie assisting golfer on course
What Caddies Do for the Game of Golf

A caddie is so meaningful to golf! Not just the round of golf that the caddie works, but the sport of golf—the complete industry of golf. Everything related to golf! Rising tide floats all boats! Nothing is more true than when you take a qualified caddie on a golf round.