The Story Behind the Infamous Caddie Who Lived at Cypress Point in a Tent

Cypress Point is one of those courses golfers dream about. It’s beautifully situated along the cliffs on the Monterey Peninsula and is annually ranked among the best in the country, right up there with Augusta National Golf Club and Pine Valley.

But the problem is getting on.

Not many people get the chance to tee it up at the Alister Mackenzie masterpiece—imagine having Cypress AND Augusta on your resume, that’s just ridiculous—but we know a few guys that have.

Pro Shop boss Chad Mumm and Wells Adams, the co-hosts of Skratch’s newest podcast Vanity Index, were lucky enough to play Cypress and Wells told his favorite story on this week’s episode.

“My favorite thing about Cypress was the story of this guy named Ray Sterbick,” Adams said. “There was a Cypress Point caddie who famously lived on the golf course. So this was years ago, he was down and out, I guess. He set up a tent between 15 and 16. He would sleep in a tent, and then he would go into the clubhouse in the morning and shower and get some food or whatnot. And now one knew he lived there, for years.”

“He ended up getting married and I’m sure moving out. His wife ended up getting cancer, and he couldn’t afford to pay for the treatment. One of the members—who I’m sure Ray was like his normal guy—was like, I got it. Took care of the entire thing. Which I think is fantastic.”

“When you’re walking by where his tent was, you have to ask a caddie if it’s okay to go visit it and if the caddie is cool with you he’ll be like ‘Yeah, come on I’ll show.’ You go through the cut and all of a sudden it opens up and it’s one of the most amazing views you’ve ever seen in your entire life. And he’s got a little bench there and there’s a sign that says ‘Ray’s Place’ or ‘Ray’s Spot.’ And then there’s a little box that’s got tequila in it and you can have a shot of tequila if there is some. You gotta pour one out for Ray.”

*Course Images via USGA/John Mummert

“Granted, I’m going between 15 and 16, 16 is the most iconic par-3 in the world. And to me, the shot you have right beforehand at Ray’s Spot, I think, is cooler than the shot.”

“It’s just such a perfect example of what golf has in its old ghosts, that I find so fascinating about golf,” Mumm said.

Mumm and Adams covered a bunch of topics during this week’s episode on top of that incredible story about Cypress.

They discussed Chad playing Pine Valley with Justin Thomas, Nick Taylor winning the WM Phoenix Open the same week that he signed on for Full Swing, Rory McIlroy working on his swing without seeing the ball flight, how the Full Swing crew impacted Sahith Theegala’s of making the TOUR Championship and much more.

You can listen to the second episode of Vanity Index on Apple, Spotify, and wherever you get your podcasts.