Cypress Point is, among golf courses, perhaps the ultimate enigma. It is one of the most famous, has been called the most beautiful and is widely considered to be one of the greatest golf courses in the world. Yet relatively few play it, there is no practice range or high-end logo-filled pro shop, the 1928 vintage, Monterey Colonial-style clubhouse, although comfortable, is quite modest and there isn’t even the refuge of what most golfers consider an adequate 19th hole.
On average, 30 golfers play Cypress Point on a given day, easily making it one of the most exclusive courses in the world. Its members come from the highest echelons of corporate and political arenas, along with a celebrity or two like Clint Eastwood and Bob Hope. All this does make a statement, however: Cypress Point is in a class unto itself, and that’s the way its estimated 200–250 members like it. Membership and golf are matter so privacy in a most conservative sense. Because we can’t see behind the veil, we want to that much more.
There is not, however, an affected aloofness at Cypress Point. There’s a dry sense of humor in the old, discarded golf bags that hang suspended from branches in a towering cypress tree behind the pro shop. Cypress Point Club, which was organized in 1926 and saw its first play on August 11, 1928, is a product of the Great Depression. That might explain some of its conservatism.
The club was the idea of Samuel F.B. Morse, founder of the Del Monte Forest enclave that today includes Pebble Beach. But ironically it was a woman—1921 U.S. Women’s Amateur Champion Marion Hollins—who charted the club’s history when she recommended Dr. Alister MacKenzie as the course architect. Hollins sold real estate for Morse and because of her success in sales and obvious connections in golf, Morse chose her to sell the Cypress Point concept.
Hollins, tremendously enthusiastic over the course site, first began to work with Seth Raynor, who had designed and built the Yale University Golf Club with C.B. Macdonald in 1926. Cypress was part of a golf course and real estate development plan that also included two courses at nearby Monterey Peninsula Country Club; Raynor had been brought in by Morse to do all three layouts.
When Raynor died of pneumonia in 1926, only his preliminary plans for Cypress had been completed. It was then that Hollis hired MacKenzie; Raynor’s plans were never used.
Of course, MacKenzie’s most famous hole is the 16th. Long celebrated as one of the most visually stunning golf holes in the world, the 233-yard par 3 is a blueprint for heroic design. Both tee and green are perched just yards from the cliff-crashing Pacific, offering no margin for error. A direct path to the pin is nearly impossible into the wind, thus most players temper their bravado by aiming for a broad bailout area to the left, and attempting a deft up-and-down. It comes as no surprise that MacKenzie originally designed it as a devilish short par 4.
Recognizing his layout could be nearly unplayable for the amateur, especially in the wind, MacKenzie made some concessions without compromising the integrity of the design. He gave golfers the option of going for broke and being rewarded if successful, or taking the safe but longer route to the green
Ed “Porky” Oliver may have seen but ignored MacKenzie’s reasoning. Playing in an early Crosby Pro-Am, Oliver took 16 strokes to finish the 16th. But the hole also has been aced six times—including one by Bing Crosby in 1947. Oliver would probably have agreed with O.B. Keeler, the biographer of Bobby Jones, who said, “the whole place resembled the crystallization of the dream of an artist who had been drinking gin and sobering up on absinthe.”
While the 16th is the most notorious, the 17th has also taken its toll on golfers. In 1990, the last year the AT&T National Pro-Am was played at Cypress, the National Weather Service reported winds up to 40 mph. Scores soared, and Ed Dougherty posted an 88, including a 14 on No. 17. Doughtery putted 11 times on the hole and later said the ball just wouldn’t stop rolling in the wind.
The 346-yard 18th has been shuffled off to obscurity by the critics, one of whom described Cypress Point as “the best 17-hole course in the world.” This dogleg-right par 4 can be a welcome oasis—uphill and partially blind in its approach and banded by a handsome cypress grove that pre-dates even the earliest golfer.
The course, which plays from extreme difficulty to relative ease depending on the weather, is not all about those famous oceanside holes, however—all of Cypress provides great golf. In fact, more than anything it’s Cypress Point’s exciting variety of terrain and golf holes that make it the grand golf course it is. Its array of hillside and wooded inland holes, open seaside holes through sandy dunes and dramatic cliff top, ocean holes make it one of the most magnificent playing fields in all of golf.
The 421-yard 1st hole is played down to a valley bending to the right and is a severe start. The second, at 548 yards, is the longest on the course and has demanding tee shot requiring a heroic diagonal carry.
After the second the course heads for a wooded hillside, the setting of the 5th through the 11th. The course then turns toward the rocky shoreline, The layout and the weather —the “beauty and the beast”—make Cypress what it is. But the greens also leave an indelible impression. Tom Kite once said, “They say everything breaks to the ocean at Cypress Point. Probably the Atlantic Ocean.”
Perhaps the most lasting—and most appropriate—description of Cypress Point came from Bobby Jones. In 1929 the U.S. Amateur was about to be played at neighboring Pebble Beach when he was invited to play a couple of rounds at the new Cypress Point Club. “Pebble Beach is more difficult, but Cypress is more fun.” Jones said in his typically diplomatic manner. His assessment rings true today for anyone fortunate to play to play this course—unless, of course the wind is howling at the 16th.
Year founded: 1928
Architect: Alister MacKenzie