When Ray Sterbick lived in the trees between the 15th and 16th holes at Cypress Point, caddie life was different. Golf bags dangled from a craggy cypress tree behind the clubhouse. Pickup games of 5-on-5 broke out on a hoop that hung next to it. Burgers and dogs sizzled on a hibachi between loops. Twelve-fifty a bag was fair.
But, even in 1982, it was still Cypress Point. The course that former USGA president Sandy Tatum dubbed “the Sistine Chapel of golf,” on par with Augusta National and Pine Valley in terms of rankings and exclusivity. It was well established even then that someone couldn’t just pitch a tent behind one of the most recognizable holes in golf and work there all summer. It was still Cypress, for God’s sake.
Unaccompanied guests at Cypress Point Club tee off between 7:30 and 8:30 a.m., Monday through Friday. Due to its international membership, the club provides this unique window for guests to play without their sponsor. The first tee box at Cypress—which sits about a mile from its more famous (and, some say, less beautiful) cousin, Pebble Beach—rests a short pitch away from a modest, one-level white clubhouse complete with green shutters. Every weekday of the year, a gaggle of the world’s most excited golfers await their name to be called and their caddie to be assigned. Nervous chatter bounces through the cool, damp fog. They pace anxiously back and forth, digging deep into their bags to find the luckiest coin and crispest white ball to charm their special day.
For the caddies, it’s just another morning. They sit quietly in the green-pewed bullpen parallel to the first tee. They stand only to help guests unload their clubs and when the caddiemaster calls their name and says, “OK, let’s get you going.” They’ve seen thousands of eager faces over the years, and they do their best to remember every one; in the caddie universe, relationships are often greater currency than a post-round tip.
“Which one of you is Ray?” I sheepishly ask them on a frigid March morning. In unison, several point toward the first tee. “The big tall guy,” I hear one say. Standing roughly 6-foot-4, with wispy white hair and double-brow-bar eyeglasses, Ray Sterbick shouldn’t be hard to miss. Yet I’m still not entirely sure it’s him. I’m looking for a scruffy 70-year-old caddie, and this guy’s holding court in the center of a growing circle of enraptured golfers, gesturing wildly and howling with laughter like a man half his age.
One after the other, repeat customers introduce themselves, all saying something to the effect of, “Ray, I played here a while back and you caddied for me. I just wanted to say thank you; it was one of the best days of my life.” Ray has a self-deprecating bullet in the chamber for every one of them: “Oh, no, must’ve been a different Ray.” “I’m sorry your life turned out that way.” “Hey, go in the pro shop and ask them for anybody but Ray today.” He keels over in laughter with each one.
As 7:30 nears, Ray gives me a Cypress 101 primer. The first two caddies off the board are an ace pairing: Vincey has been here 51 years, and Louis McIntyre started two months before Ray, in 1977. Once you find a place here, Ray tells me, it’s tough to carry anywhere else. And it’s not only the caddies. The current head pro, Casey Reamer, is just the fourth in Cypress history since the club opened in 1928. Greg, who worked in maintenance and the kitchen before his current gig in the locker room, has been here for 34 years. “It’s a family,” Ray says. “A dysfunctional family, but it’s a family.”
I’m just catching on to Ray’s funky, almost Canadian accent when his name is called. We make plans to walk the course later that afternoon and check out “his spot.” As his group embarks on one of golf’s most sought-after walks, he turns back to me and demands I head down the coast to take in “one of the most beautiful places in the world”: Point Lobos.
Someone says it every year on the Pebble Beach telecast: The coast along Monterey, California, is “the most felicitous meeting of land and sea in creation.” Most, including Sports Illustrated in 1999, attribute the quote to prolific Scottish author and Monterey resident Robert Louis Stevenson. Well, he may have said it, but he wasn’t the first. Francis McComas—a Tasmania-born landscape artist who settled in Monterey near the turn of the 20th century—originally described Point Lobos State Natural Reserve as “the greatest meeting of land and water in the world.”
While McComas was an original member of Cypress and led the committee that oversaw design and construction of the clubhouse, very little is known about his life outside of his art. From what scholars can gather, he left Australia for San Francisco in 1898 and quickly gained traction in the local art scene for his subdued style of what became known as California Tonalism, before reinventing his technique with bold colors and sharp geometric patterns. In 1910, Bay Area press speculated that he was the most expensive watercolorist in the world. By 1920, he was off the grid. It stayed that way until his quiet death in Monterey in 1938. Until 2017, nobody even knew where he was buried.
McComas is but one in a rich history of poets, artists and boss movers who fell victim to the Peninsula’s devastating beauty. Before Eastwood, Crosby and McComas, there was Samuel Morse. Not the Samuel Morse who invented the telegraph—that was his cousin—though golfers may argue this Morse was more impactful. After ownership of the land moved from the Ohlone tribe to Spanish missionaries to a speculator named David Jack—who named the area’s popular white cheese Monterey Jack—it fell to Morse, a 32-year-old Massachusetts native who was the first to realize the golf potential of the 5,200 heavily forested acres that sat between Monterey and Carmel.
Having seen the economic boost Donald Ross’ course had given Pinehurst, North Carolina, Morse was certain golf was America’s next big thing. After commissioning Pebble Beach and Monterey Peninsula Country Club as his hotel’s first two offerings, he still wasn’t satisfied. So he turned to his company’s savvy athletic director, Marion Hollins. A decorated amateur player, Hollins knew what was required for great golf and suggested he build on a gorgeous 150-acre plot just north of Pebble that the Spanish called “La Punta de los Cipreses.”
Morse agreed, but he wanted to build a tame resort course. Looking at the landscape, he was sure whatever they built there would kick his hotel guests in the teeth. Hollins knew what she had found was special, and lobbied hard for Morse to turn it into the most exclusive club in the world. Morse agreed, and helped to finance her plan. Nearing completion on his work at nearby MPCC, Seth Raynor was Hollins’ first choice to execute her vision. But as Raynor was sketching out Cypress routings in 1926, he died suddenly of pneumonia.
Just a short drive up the coast, Dr. Alister MacKenzie had recently landed in America in search of work. The British front-line surgeon turned defensive camouflage specialist had only recently resumed his career as a golf architect following World War I, and, through a chance encounter with famous author Robert Hunter, had found a few commissions in San Francisco. Impressed with his work, Hollins brought MacKenzie to see the property. MacKenzie realized immediately what he’d been handed.
“I do not expect anyone will ever have the opportunity of constructing another course like Cypress Point,” reads a MacKenzie quote on the back of the Cypress scorecard, “as I do not suppose anywhere in the world is there such a glorious combination of rocky coast, sand dunes, pine woods and cypress trees.”
Before 17-Mile Drive was slapped on headcovers and whispered by Jim Nantz between Kenny G swing breakdowns, it was a sightseeing trail that ran from Pebble Beach to Carmel. As part of their stay, Morse’s hotel guests would pile into a horse-drawn carriage and ride south along the sea. Eventually they’d arrive at “The Loop,” where a thin strip of land gave way to a jutting rock formation that offered an unparalleled, fully exposed view of the coastline. It was here that Hollins was certain she’d just discovered the world’s most spectacular par 3.
Raynor and MacKenzie had their doubts. By all accounts, both men believed that it should have been a par 4; the 200-plus-yard forced carry would be too much to ask of everyday members. Legend has it that, to prove her position, Hollins dropped a ball in front of Raynor and, while wearing a tweed blazer, flushed it through the wind and into the heart of the green. It stayed a par 3. Today, whether you play it in 3 or 4 or 5 or 6, there’s no debating that No. 16 at Cypress is no longer a leisurely carriage tour.
Nearly a century later, just behind where Hollins struck that famous shot, another shocking discovery was made. After years of searching, art scholar Robert Pierce had narrowed his hunt for McComas’ grave down to the thickly wooded cliffs overlooking Cypress Point’s 16th hole. After getting permission by the club, he stumbled across a pale boulder some 20 feet from the cliff’s edge. On it, a faint carving read, “Francis McComas 1874–1938.”
Next to the rock sat two redwood benches, some scraps of old, damp plywood, a bottle of tequila and a freshly carved wooden sign.
Ray was struggling to make ends meet as a caddie on the PGA Tour, and he was willing to do anything to caddie at Cypress Point. He would do anything to caddie, period. Since he was 8 years old, it was all he’d known.
Ray picked up his first loops as a boy at Fircrest Golf Club in his hometown of Fircrest, Washington. Back then, a day’s work earned him a bacon cheeseburger and a milkshake. As he later found out, the Tour didn’t offer much more if you weren’t cashing top 10s. Ray’s father, a prominent lawyer and community figure in Fircrest, had sponsored a promising young player from the local club named Ken Still. Ray was assigned to his bag part-time, and was quickly hooked by life on the road.
Ray grew up the third of eight siblings—six boys and two girls. Five of them would follow in their father’s footsteps, becoming lawyers. The others founded nonprofits helping battered women and the homeless. Ray was drawn to the golf course, but by the time he got to Cypress, he was also searching for a roof over his head.
After making the 1969 Ryder Cup team (famously ending with the Nicklaus-Jacklin concession) and notching three wins between 1969 and 1970 (none with Ray on the bag), things slowed up for Still. By 1977, he had his eye on the Senior Tour and played sparingly throughout the year. Looking for a steady gig, Ray made his way to Monterey in hopes of picking up a job at the area’s PGA Tour event that was then known as the Bing Crosby National Pro-Am.
He managed to get an amateur’s bag that week—since this was the height of the Crosby Clambake, his amateur just happened to be Alan Shepard, the astronaut who in 1971 famously hit the first golf shot on the moon—and, like so many before, fell for Cypress Point. He loved the ocean more than anything—the sound, the smell, the feeling of freedom. Following the tournament, Cypress’ then-caddiemaster, Joe Solis, approached him: “You want to stay in that zoo out there or you want to come caddie for me?” Ray readily agreed. But with seniority dictating the work at Cypress, loops were scarce. Ray knew he needed to make an impression if he wanted to make this opportunity work.
Richard Kehrer, or “Coop,” as they called him in the caddie barn, was the first to show Ray the ropes. His first lesson: You didn’t need a big house to live like a king. Coop would park his car down by Monastery Beach, just north of Point Lobos, and pitch a tent made of plywood and plastic to keep the drizzle away. Back then, as long as you moved your car 6 inches once a week, you could stay forever. Camping on the beach, however, was not allowed.
“Don’t you see the ‘No Trespassing’ sign there?” Ray asked.
“Have you ever looked at the back of the sign?” Coop responded. “It doesn’t say a word.”
Ray bought in. He tried cutting out the seats of his 1955 Dodge and laying plywood down to sleep on. He tried building Coop’s “hobo huts.” Slowly but surely, he started inching his way farther up the beach toward Cypress, eventually camping close enough to where he’d run to work each morning and hitch a ride home.
“You can’t live like this, with no insurance,” his mom would tell him when he returned to Fircrest in the winter. “I have God for insurance,” he’d reply. “God’s not going to pay the premiums,” she quipped. But every spring, Ray would make his way south.
Together, Coop and Ray started the Hobo Society. Coop was El Presidente and Ray was A-1 Hobo. Fellow caddies took part. There was Mark Toole, Sergeant-at-Arms, and Louis McIntyre, Vice President. While Cypress members would carry on with stars and moguls during the tournament, “hobos and hobe-ettes” from far and wide would gather down on Bird Rock, just between Cypress and Monterey Peninsula Country Club. The bonfire would roar; drinks would flow; Ray would sing along as Coop strummed guitar to one of the 200 songs he’d written.
Skipping stones across the river Skipping stones across the sea Skipping stones across this mighty country To see what I can see
By 1982, Ray was living in the bed of a truck outside McIntyre’s dad’s house. He was working part time at Cypress and taking jobs on Tour whenever he could for extra cash. One day, as he made his way from the par-3 15th to the par-3 16th (which Ray calls “the most beautiful” and “the most incredible” golf holes in the world, respectively), years of avoiding No Trespassing signs caught up to him. The trees to the right of the path were so dense, and the limbs so thick, that nobody would ever be able to tell if someone was living in them, he thought. That night, in the pitch dark, he wandered down behind the clubhouse to check it out for himself. He heard the waves crashing beneath the cliff and took a deep breath of the fresh sea air and cypress bark that surrounded him. He looked back toward the clubhouse. All he could see were tree limbs.
The idea was either downright crazy, MacKenzian in its camouflage or both. Either way, Ray was home.
The next night, he gathered up some spare wood and a handsaw from the ongoing clubhouse renovations. He put Coop’s lessons into practice, fashioning a hobo hut that would keep the rain out and insects away. He’d still need to watch out for raccoons, but it was a small price to pay for waterfront Monterey property.
The following night, McIntyre helped Ray move the mattress out of his truck and into his new crib. “Of course I thought he was a little crazy,” McIntyre says after another day’s work at Cypress, 45 years later. “But he’ll probably tell you he had the best sleeps of his life right there.”
For the next eight months, that’s exactly what Ray did. He slept like a baby to the sound of waves crashing off one of golf’s most famous holes. When everyone left for the day, he ran up to use the employee shower behind the clubhouse (technically off-limits for caddies), then returned home. He fashioned meals using some stolen cutlery from the caddie barn. He made omelets and sandwiches on the hibachi after his first 18 of the day. And, with a much shorter commute, he was first in the bullpen every morning.
“How’s Ray here first all the time?” other caddies would grumble. “Where does he even live?”
“He doesn’t even have a phone number; how does he know when he’s supposed to work?”
Rumors circulated. Ray didn’t care. He continued to show up first every morning and soon became a part of Cypress’ DNA. He endeared himself to head pro Jim Langley, who in time became a father figure to him. Members fell in love with his witty one-liners, yarn spinning and sunny disposition. He was part of the family. Had anyone found out where he was living, Ray would have been fired on the spot. McIntyre too, for his part in aiding and abetting.
When the insects finally broke through his hut and the coastal winds turned frigid, Ray went home to Fircrest for the winter. When he returned the following spring, he met a woman and moved in with her. “I was domesticated,” he prefers to say.
Until McComas’ headstone was discovered, the story of Ray Sterbick in 1982 lived in folklore among a handful of caddies and trusted members and guests. Why nobody turned him in is anybody’s guess. Maybe they didn’t believe anyone could be that crazy. Maybe they knew and didn’t care. Or maybe they knew exactly why he did it: Ray would do anything to caddie at Cypress.
“I have the greatest commute in the world,” Ray says after picking up lunch at his Pacific Grove home five minutes down the road. “And then I get here and I have the greatest office in the world.”
After his morning 18, Ray’s 70-year-old body is somehow ready to walk the course again. He’s shed his bib for a brown Nanea Golf Club quarter-zip and a shamrocked hat with “Live Lucky” underneath the bill. He smiles wide, showing the slight gap in his two front teeth, telling me that everything he’s wearing came from generous members. We set off down the first hole and pass through the 10-foot hedge that blocks a thin strip of 17-Mile Drive from nervous tee shots. The hedge wasn’t there when Ray first started, he tells me. It was a small white fence. One day, Mrs. Dart, whose husband, Justin, was the famed drugstore magnate and chairman of Dart & Kraft Inc. in the 1980s, shanked one off the first tee and nearly clipped the driver of a white Cadillac convertible. The next day, a hedge appeared.
As we walk the course, Ray’s stories tumble out like an erratic range session. Like the time when Tiger came to play and went for the green on the par-4 13th, only to push it right into the window of a Maserati passing by Fanshell Beach. Which reminds him of the Hobo Society gatherings he had there with Coop. Which reminds him of the time he hitchhiked from Alexandria, Virginia, to Fircrest. Which reminds him of Langley, who tied the course record—63, a distinction he shares with Reamer and Ben Hogan—before getting hit by a car and nearly losing his left arm.
Each memory sparks a new story. Every thought bleeds into the next. He doesn’t stop other than to shovel in a handful of peanuts he’s brought in a lime-green plastic bag. His mouth has been moving for nearly a half-century.
“Don’t you ever stop?” Cypress member and Seminole Club President Jimmy Dunne once asked in the middle of a round. “Are you getting paid by the word? Are you Charles Dickens?” The next day in the mail, Ray received a package from Dunne. Inside was a Dickens novel and a note: “Read more, talk less.” “Most people don’t understand the New York humor,” Ray laughs. “I like it.”
Banter is one of the things Ray loves most about his job. To him, humor is the great equalizer, especially with new guests. Playing a place like Cypress for the first time can feel like walking on golf history’s eggshells, and sometimes pulling out a good line on a first-timer is exactly what’s needed to break the tension.
“I like going to the edge,” he says of his jokes. “If you’re going to have fun, you might as well go over the edge and look at the view to see how far you’re going to drop.”
Ray’s first and only professional win as a caddie came on the Senior Tour in 1989 at California’s Ojai Valley Inn, where he picked up a job for Walter Zembriski, a short, mouthy former steelworker from New Jersey. The week before, Ray had been working for a different player in Las Vegas when, on the opposite fairway, he saw a caddie pick up the bag over his head and heave it at the notorious hothead. When Ray got to Ojai and linked up with Zembriski, caddies were taking side bets on how long he’d last.
“I made him laugh,” Ray remembers. Zembriski shot a final-round 65 and Ray collected $5,600 for his work.
Ray believes there are two types of caddies. There are golfing ones—the sort who read greens well, club their player properly and abide by the old axiom of shutting up and staying out of the way. Then there are tour guides, whose job is to create the best possible experience for their player in hopes they remember it for the rest of their life.
“When people go into the pro shop after a round and say, ‘I had the best time ever today,’” Ray says, “that’s what makes me happy. That’s what I live for.”
Part of that experience includes taking players by his old home, where he’s stashed a bottle of Don Julio and a few shot glasses. He built those wooden benches that offer players a jaw-dropping view of the 16th green and a nice place to take a break and listen to stories from the summer of ’82. Tom Watson once asked if he could see it. Steph Curry stopped to take a picture there. The club brass has quietly accepted Ray’s tour as part of its unique culture. Andy Delhamer still can’t believe word ever got out.
Delhamer started looping at Cypress in 1985 and became fast friends with Ray, eventually asking him to be the godfather to his daughter, Maddy. Over the years, whenever he’d caddie alongside his pal, he’d hear Ray tell the story as they walked from 15 to 16. Finally, a few years ago at the Monterey County Fair, he brought a slab of wood and asked a local artist to etch him a sign: “Ray Sterbick Lived Here 1982.” Every great tourist attraction needs a proper marker.
“Ray has a lot of God in him,” Delhamer says. “Outside of Cypress Point, the only things that matter to him are love and kindness.”
When Ray was 8, the Tacoma school board began desegregating local schools. The decision was unpopular, as neither Black nor white families wanted their children to ride the same school bus. Ray’s father was on the school board, and soon their house was swarmed with protestors. One night Ray’s mother whipped up a plate of chocolate-chip cookies and a pot of coffee and told Ray to take them outside. Ray marched right up to the local Black Panther Party and offered them a warm cookie.
“That’s called killing them with kindness,” Ray says with a smile. “I want my legacy to be that I was kind, I was compassionate, I was generous with whatever little I had and I made people’s day out here.”
He’s collected coins his whole life, and now passes them on to members’ children in hopes they’ll start their own collection. Each year, he makes calendars featuring photos he’s taken of the course and its wildlife. Every winter, he returns from Fircrest and passes them out to the members who’ve kept him afloat all these years. If you ever write Ray a thank-you note, you’ll get a calendar until you or he dies. On the day I’m there, three separate members ask if they’ll be receiving one this year.
To the titans of industry and CEOs Ray regularly caddies for, coins and homemade calendars pale in comparison to what they give him. Over the years, Cypress members have tipped him generously, clothed him, given him places to stay, taken him on 12-day trips to Scotland and offered assistance through the pandemic. Ray is forever appreciative, but looks beyond the financial value.
“I don’t care how much you’re going to pay me, because you can only pay me so much money anyway,” he says. “If I haven’t made my money by now, I’m done. I’m being honest: I’m not going to get ahead. I want kindness and compassion. Because to me, if you show kindness and compassion and are generous, then you are giving. That’s what I want.”
When we arrive back at the clubhouse, Ray stops to stare at the flagpole just behind No. 18. It’s at half-mast today, signaling that one of the club’s roughly 250 members has passed. Somewhere, it’s a sad day. And somewhere else, it’s a glorious one. One of the greatest invitations in golf is headed their way.
Ray knows his time is coming. He thinks about it often. He never moved out of that woman’s place. They’re still together, but never had children. He watched his father pass after a struggle with Parkinson’s disease. Then he watched Langley be robbed of his mind and body by ALS. Before things got too bad, Ray’s dad was able to visit his son’s office and play the course. On the first tee, the caddie barn gave him a standing ovation. Before Langley lost his motor skills, he pulled Ray aside and asked him for a favor: “Keep the family together.”
Ray’s seen countless members, some of the world’s richest and most powerful figures, fall victim to time’s relentless march. His mom and Coop are now gone. Every time, the world keeps going. He shows up for work the next morning. Bag up, bag down. Insert joke here. Older cypress trees thin out. The flag goes to half-mast, then returns to full. Somebody gets a letter. The clock keeps ticking.
For the rest of his days, Ray just wants to walk. He believes walking is the greatest sport in the world, one in which there are no winners or losers, one where very few, if any, die while doing it. He wants to sit on Delhamer’s back porch and drink one of his famous Moscow Mules from a chilled glass. He wants to hear the waves crashing as he falls asleep and breathe in the ocean air as he emerges from inland holes on the back nine. He wants to make people laugh and hear that they remember the day he carried their bag. He wants to pour you a shot and gaze across the water at the floating rock that they say God made for golf. He wants to put on a Cypress bib and call himself a Cypress caddie for as long as they’ll let him.
I read the underbill of his hat and ask if he feels lucky to have been one all these years.
“I don’t believe in luck,” he says. “Luck is a percentage. I believe that I’m blessed. I believe everybody is blessed. That’s a 100% guarantee. It ain’t a percentage. For me to work here every day and be surrounded by nice people, I’m very blessed.”
His eyes leave the flagpole and meet mine, and we say goodbye. He hands me three calendars and makes me promise I’ll give them to people who deserve it. I’m almost out of Monterey when I stop at a red light. An elderly woman with a green-and-red-striped beanie sits on the sidewalk just outside my window. She’s holding a cardboard sign: “At the end, all we have is kindness.” The light turns green.