How the 16th Hole at Cypress Point Was Made l The Hole At l Golf Digest

Welcome to ‘THE Hole At’, where Golf Digest’s Derek Duncan (our go-to for all things golf course architecture) breaks down the hidden histories behind the most famous holes in golf. In this episode, Derek dives into America’s Greatest Golf Hole, the famous long Par-3 16th hole at Cypress Point Club. From its original routing by Seth Raynor and Marion Hollins, to the final execution by Alister MacKenzie, to remaining one of the most daunting and majestic holes in the world, Derek explores the fascinating history behind one of the game’s most iconic golf holes.

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Host: Derek Duncan
Producer: Ben Walton
Editor: Robert Phillips-Knight
Audio: Tony Leonardo
Executive Producer: Christian Iooss

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Chapters:
0:00 Intro
0:34 The Hole Today
4:03 How To Play It
6:00 The Origins of Cypress Point
7:30 Seth Raynor & Marion Hollins
8:15 Par-3 or Par-4?
9:30 Enter Alister MacKenzie
12:15 Minimalism Construction
13:30 Changes to the Hole
14:15 How Pros Stack Up
15:13 Whatever It Takes
16:15 Final Verdict

Picture this. You’re standing on an exposed outcropping of land looking toward the Pacific Ocean. On the horizon, across the roar of pounding waves, is an archipelago of a rock. And on it, a golf green perched above the water and framed in sand, the flag stick bent in the wind. It could only be one place. Hello, I’m Derek Duncan, the architecture editor at Golf Digest. And today we’re going to be taking a look at one of the most sensational, beautiful, and difficult holes in golf, the par 316th at Cypress Point Club on California’s Mterrey Peninsula. For golfers, there are few things more exciting than playing holes along and over vast bodies of water. The challenge of hitting a shot from one edge of land over the ultimate hazard of the ocean to another edge of land. It’s as thrilling as golf gets. Cypress Points 16th is the world’s most extreme example of this experience. It has everything we desire in a golf hole. Drama, sensory overload, majestic scenery, tension. Let’s take a look. The hole as we know it was designed by Alistair McKenzie in 1926. Though it’s a little more complicated than that. It’s more accurate to say the hole was discovered that it had been waiting there for the arrival of golf to this westernmost point of Montterrey Peninsula for eons. Then in the summer of 1928, this hole in all of Cypress Point opened for play. As you come off the 15th green, which is also one of the world’s most spectacular oceanfront par 3es. Yes, Cypress Point has backtoback par 3es, and for that matter, backto-back pars. You travel on a foot path 120 yards through a forest of twisted cyprress to emerge into the vast amphitheater of the 16th hole to what the late Sandy Tatum called the cyine chapel of golf. [Music] The one-of-a-kind arena of golf explodes before you. There’s a crescent of low cliffs that bank around the far side of the cove circling to the right out to the point on a rocky ithmas directly across where the green is set. Below is the Pacific Ocean crashing against the coastal rocks and a sandy beach to the left of those TE’s. The TE’s are set on rocks. The back tees are elevated and from there it’s a shot of 230 yd to the center of the green and just over 215 yd to reach the front. From the next set forward, farther out on the rocks, the shot is 215 yards to the middle and about 200 yd to safety. Another set of T’s to the left shorten the distance to the center of the green to about 205 yards. The green is the largest on the course, 35 yd deep and about 7,500 square ft. While that may seem to be a big green for Cypress Point, it’s not that particularly large overall. The average green size for courses in the United States is around 6,000 square ft. So considering the length of the incoming shot at 16, 7,500 ft actually feels pretty small. The putting surface is surrounded by six bunkers. Two of them flank the front and three sit behind it, banked into the UPS slope. These bunkers set up the green visually and also protect the T’s for 17 which are leveled above them on the high point. And we’ll talk more about this small little bunker in a minute. Because of the long and heroic nature of the T-shot, the green is fairly flat and receptive all things considered is tilted slightly toward the ocean with the land behind providing a back stop. Bill Kr who along with partner Ben Krenshaw consults with the club describes the green as a flat pancake at first glance. But within the oval shape are all kinds of subtle twists and turns that can make balls do unexpected things. The green also putts a little different than the others at Cypress Point. Since the poanua grass on it is growing under some, shall we say, unusual conditions. That’s what happens when you put a green on essentially an island in the sea. It evolves its own distinct character. The real danger of the green is the rolloff on the front right. Shots that don’t get all the way up and over it can easily dip back off the green and could even tumble down onto the beach below the protecting seaw wall. Going for the green with all the scenery, length, pressure, and emotion swirling around is one of the most daunting shots imaginable. It’s an all or nothing carry that can be next to impossible when the wind is blowing against the tea. Penal par 3 shots like this can be terrifying and controversial. There’s a long storied history of famous or infamous palm sweating holes where your ball either finds the green surface or you’re in a world of hurt. Think of the island green 17th at the stadium course at TPC Srass. The posted stamp at Royal Trune. The short 10th at Pine Valley, the 17th at Seol ringed in a necklace of sand, and even the 12th at Augusta National where the shot has to clear raise creek. Cypress Point’s 16th just happens to be a much longer version of this kind of par 3. It’s asking you in no uncertain terms if you have what it takes to make the shot. But that’s not all there is to the hole. Yes, you can choose to go for the green, but you don’t have to. We haven’t yet examined all of this area to the left. This broad expansive fairway blending into the 17th hole gives golfers the option of laying up if they’re not comfortable taking on the long carry. And it’s this choice that turns an otherwise severely penal hole into a highly strategic one. Depending on the wind and the player’s ability, the T-shot to the fairway could be anywhere between 135 yd to 175 yd. McKenzie recommended that players who couldn’t reach the green aim at the lone leaning cypress in the fairway, which is now more of a memorial trunk left over from the original tree, and let the natural fade carry the ball into a garden spot short of the green. From there, they could try to pitch on in one putt for a three or two putt for a four at worst. This is where that sixth bunker left of the green comes into play. It creates a narrow gateway in the neck, so approaches from the left usually have to fly all the way onto the putting surface. Even before a course was built there, Cypress Point was being talked about as one of the country’s greatest places for golf. People would mention hearing about the site to McKenzie during his travels across the country, even back on the East Coast. He later called it the best golfing terrain he’d ever had to work with. It had some of the most astonishing ocean frontage anyone had ever seen. But it also had natural variety. The land rose and fell gracefully and moved through distinct ecosystems, including interior foothill forests of Monterey Pine, open dunes of white sand, and finally the rugged rocky coastline. Developers had been fascinated by the lucrative potential of the site for years. But it wasn’t until 1924 that Marian Holland, arguably the best female player of the era, began working with Samuel Morris to develop the site into something more than just real estate. Morse, who created Pebble Beach in 1919, owned over 18,000 acres of Delmonte forest on the Monterey Peninsula through his Del Properties Company, including 150 acres that would eventually become Cypress Point. In February 1925, Hollands optioned the property from the Delmonte Properties Company and began developing the golf course and club. And by 1927, she had secured enough members for the club to be officially incorporated. So, it’s absolutely correct to say Cypress Point and the 16th hole would not exist as we know it without Marian Holland. She was the brains and muscle behind the club. The architect she selected to design the course was Seth Rener, one of the hottest architects in the US at the time and a man whom she knew from a previous project back in New York. Rener, the surveyor and understudy of Charles Blair Macdonald at National Golf Links of America way back in 1911, had recently remodeled Chicago Golf Club and was in the midst of building masterpieces like Fischer Island in the Creek in New York, Kamargo in Cincinnati, Yale, Yaman’s Hall in South Carolina, and Lookout Mountain near Chattanooga. Rainer was also tapped to build the two courses at another Morse Delonte venture, Montterrey Peninsula Country Club, just up the coast from Cypress Point. In fact, the first course at the Country Club had already begun construction in 1925. During one of his visits that year, Rainer explored the Cypress Point property with Hollands and developed an initial routing for the holes, including the original plan for the 16th. Like any architect worthy of his business card, Rener identified the spot out on the Rocky Peninsula as the ideal location for a green, but his hole was intended to play as a par4 from the tea back in the Cyprus closer to the 15th green, driving out to the broad basin of fairway to set up the short approach and from the side. It’s a pity the green is too far away for the hole to be a par three, he said to Hollands as they stood looking out at the arrangement of rock and ocean. Hollands insisted it would not be too far of a carry for the members, but Rainer was dubious. So, she set a ball on the ground, pulled out of her bag what was allegedly a brassy, the equivalent of a two or threewood today, and promptly stroked it over the water where it landed in the area where the green would eventually be. Problem solved. The 16th would work as a par three. Now, there were no other witnesses to observe this shot, so there undoubtedly could be some degree of mythmaking in the story. But remember, she was one of the most accomplished women players of the day and also one of the longest. So, there’s little doubt she could execute the shot. What Rener thought exactly is moot because he passed away from pneumonia the following January. It remains one of the great unknowns in architecture. Rainer had never gotten beyond figuring out where the holes would go, but in all of his other designs to that point, he built versions of the holes he and Macdonald developed at National Golf Links, including templates like the Redan, the road hole, the Alps, a cape, and so on. His shaping on these templates was angular and geometric, a look that was usually intriguing in inland or park-like settings. But how would that style have fit on a rugged, sandy, windswept site like Cypress Point? Could he have made those sharp shoulders work? Or would he have adapted the design to the naturalism of the land? We’ll never know. What we do know is that Holland needed to find a new architect. Enter Alistair McKenzie. In February 1926, Hollands met with McKenzie and impressed with his international resume and confident Scottish disposition, Holland hired him to complete Cypress Point. It began a working relationship between the two that would last the rest of the architect’s life, leading him directly and indirectly to the jobs at Augusta National and Posato. McKenzie tinkered with Rainer’s rudimentary routing, but kept the holes generally occupying the area where they were. This was largely because there weren’t many options giving the preferred location of the clubhouse, the rocky coast, the home lots on the periphery, and the other property boundaries that meant the Gulf had to fit into defined sections of land, much of it long and fairly narrow. McKenzie merged holes together, then broke them apart. New T’s were added and shifted. Par 3s became par4s, and entirely new holes were drafted to better utilize the dune section of the property. He didn’t mess around with the last four holes, which Rainer and Hollands had out on the rocky rim of the Pacific. The opportunity to climax the round over the pounding surf was already an ideal sequence of holes, the kind every architect dreams of, but rarely if ever sees. Curiously, McKenzie and partner Robert Hunter, who oversaw the construction of the course, also thought the 16th should be a short par4 rather than a par three. and early listings of the course actually listed as a par4. But Holland was the founder of Cypress Point and it was ultimately her decision. As he and Hunter examined it and saw enough other people demonstrate the carry across the cove, including professional players like Bobby Krookshank and Tommy Armor, they began to understand the beauty and strategic complexity of the hole as a par three. It had both penal and heroic elements. In fact, in later years, McKenzie gave Hollands full credit for the brilliance of the 16th hole. The construction of Cypress Point was also innovative. Under Hunter’s guidance, they had specialists test the site’s different soils to match them with the ideal grass seeds and fertilizers. They removed hundreds of trees to clear holes and open views of the ocean and pushed the boundaries of the fairways out to make space for McKenzie’s bunkering and different strategic routes. Even in the earliest photos, the course looks nature, like it was already there and just needed grass. Cypress is a trick of early minimalism. Each greenside and all of the fairway contours were created, crafted manually by a team of their best shapers. All the movement was tied together by the sand and the bunkers that were built and edged in great detail. The same windswept motifs carry through the different pockets of the holes, transitioning from the trees to the dunes to the sea. McKenzie’s bunkers surrounding the 16th green miraculously look natural even though there’s no sand out on the rocky point and it had to be covered in top soil. Over the years, those bunker shapes have morphed and evolved as will happen when you place them in the middle of the tumultuous ocean. At times in their life, they become rounded and less defined. But the McKenzie forums have steadily been reclaimed in the last few decades by Superintendent Jeff Marau and his staff. The only change of substance to the hole was the division of a single large bunker at the back left of the green into two smaller bunkers, restoring it to the way it was originally. In early photos, you can see here that the now famous 17-mi drive once went right out to the point. The road was shifted inland when the course was built and now moves behind the 14th green and cuts through the course between the clubhouse and the first fairway. The embankment below the green has also been reinforced. As early as the 1970s, stone pilings were built to fortify the land above the beach. In the late 1990s, a more substantial seaw wall was constructed under the green, saving the land from further erosion. Other than that, the hole is pretty much the same today as it was in 1928. Though it’s one of the most posterized holes in the world, we rarely get to see people play Cypress Point 16 aside from the 2025 Walker Cup. But the course used to be in the rotation at the AT&T Pebble Beach ProAm, formerly known as the Bing Crosby, from 1947 all the way up until 1990. Official tour statistics only go back to 1983, but the course more than held its own against the professionals in the last years it played host with an average score of 74.3 over its relatively short 6,500yd par 72 design. The 16th hole fared even better. The scoring average between 1983 and 1990 was an incredible 3.64 strokes. It was the hardest hole on the PGA Tour five times in that time span and was never outside the top five. Rainer, Mackenzie, and Hunter all wanted it to be a par4, and they kind of almost got it. Cypress Point is a very private club, but if you’re ever lucky enough to play it, you’ll be faced with the major decision on the 16th T. Go for the green across the stretch of ocean or lay up to the left. One word of advice. If you do decide to take your shot, and why not, you only live once, take more club than you think you’ll need. Hitting through the green or even into the back bunkers is a far better outcome than ending up short. The number of balls that end up on the beach or in the water short outnumber the balls that actually do go over the green, probably by a 20 to1 margin. And going over the back edge of the ismas isn’t likely because of the bunkers in the UPS slope. Though, if you do pull your driver too much, the ball could bound through the fairway left and down onto the rocks. If that happens, the ever colorful Jimmy Demerit once observed, “There’s no relief. The only place you can drop a ball from back there is Honolulu.” So, there’s no shame in hitting a three- metal or even a driver here. The mantra should be whatever it takes. If you do hit driver, you certainly won’t be the first. So, let’s put the 16th hole at Cypress Point into context. It’s the most famous and most spectacular hole at the course that’s parentally ranked number three on our list of America’s 100 greatest courses. Golf Digest panelist also voted it number one in our America’s 100 greatest holes ranking. It’s beautiful, original, majestic, and frightening. Alistister McKenzie said that for strategic problems, thrills, excitement, variety, and interest, he didn’t think there was a course in the world that could come close to the old course at St. Andrews. The completion of Cypress Point, he wrote, has made me change my mind. Without the 16th hole, you wonder if Cypress Point clears that bar. Thanks for watching. If there are other great holes you’d like to see us break down, please let us know in the comments below.