Henry McCray is not your typical caddy. He and his family bounced around from state to state for most of his childhood. He eventually attended a boarding school in Connecticut. After his father passed his freshman year of high school, he decided to focus on his passion: Sailing. He had been sailing and racing since he was 6 years old. It’s a big part of Henry’s life. He sailed growing up, in college, for the US Sailing team, and has sailed on 3 different oceans. Sailing is even how Henry was introduced to golf and caddying.
When did you learn about golf?
“Golf came to me as a young adult.” Henry said. At a sailing regatta with no wind, he was sent ashore and told to wait for a minimum of three hours for the wind to pick up. A friend invited him to hit a golf ball back and forth in an adjacent field. His friend grabbed a pitching wedge, and handed him a seven iron. Knowing virtually nothing about golf, he asked "Isn't a seven iron supposed to go a lot further than a Pitching Wedge?". "Yes," his friend replied, "But you've never hit a golf ball before." Standing about 120 yards apart, his buddy hit the ball towards Henry. It was his turn. “I hit that ball 70 yards over his head- into the water. I was hooked.” Henry said.
Luckily for Henry, a family friend was retiring from the LPGA tour and was recruiting him to teach her how to sail. So they made a deal-he teaches her to sail, she teaches him golf.
When did you start caddying?
Most caddies start looping as a kid at the local course, or in college, or once their golf career is coming to a close. Once again, Henry’s story is unique.
“Through luck and circumstance, I ended up carrying a bag on the LPGA for a four event span in the early 2000's. I wasn't very good, I had no confidence. I just didn't want to screw up.” Henry said.
His caddy career began at the highest level of golf: the LPGA Tour. Henry started caddying full time at the Ocean Course after a tough year in 2007. He found out he had cancer, his wife left, and he lost his business and home. “I know, one hell of a year.” Henry said.
After 15 years and “Conservatively” 3500 loops, Henry still loves coming to work at the Ocean Course. At least, most of the time.
What is your commute to work like?
Most caddies at the Ocean Course live in Charleston and have a 45 minute drive to work, but Henry lives right around the corner.
“I live a mile from Kiawah. My drive to the Ocean Course takes 19 minutes, but I usually stop at the store for a Red Bull and some smokes. Before my loop I ask myself- fresh socks? warm enough? Rain? I check my jumpsuit or bib- two scorecards, three pencils, chapstick, Neosporin, band aid, Laser, smokes, lighter. Sunglasses on my head, uniform hat. Let’s go to work”
How do you help your players play better?
Henry told me this was a truly dynamic question, which is the exact response I would want to hear from my caddy. He starts caddying before the first tee shot is ever fired off.
“First, I establish rapport. Earn trust. Determine personality type, athletic ability level, and unlocked potential. I will try to do all of this before offering any ‘swing’ advice.”
Establishing rapport is crucial when caddying for a player for the first time. If the player doesn’t trust or have confidence in the caddy, it will not be a good 5 hour relationship.
Henry also knows the reason why 99% of golfers play: to have fun. “I have had guests laugh their way around the course- because that's what they wanted.” Henry said
For many players, having fun on the course doesn’t necessarily mean shooting a great number. Some golfers play for other reasons-to relax, to enjoy nature or just to get outside. That is one of the greatest aspects of this game-you don’t have to be good at it to have fun.
Player: “Can I reach that bunker?” Henry: “Not unless you’ve been hiding something from me all day, sir.”
Favorite Caddy Story?
“I had a guest tell me he was from New Canaan, CT. I told him I lived there as a child. ‘Where did you live?’ the guest asked and I repeated the address. He dove back into his golf bag and looked relieved to find his wallet. ‘How did you know where I live?’ he asked. I suddenly realized what had just happened, and began to describe the house. It was his house, and my old house. What are the odds of that? We had a great day.” Henry said.
Favorite thing about caddying?
“I find great enjoyment in helping our newer caddies and changing the caddie culture as a whole along the way. I love replying to rhetorical questions. I love watching someone exceed their expectations.” Henry said.
What have you learned from caddying?
“The better question is what I haven't learned. It presents you with an opportunity to learn. When you choose to cherish each opportunity the amount you can learn becomes limitless.” Henry said.