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Hole With a View

From the elevated tee on Cypress Point’s 17th hole, above Pacific waves roiling against the rugged shore of California‘s Monterey …

From the elevated tee on Cypress Point’s 17th hole, above Pacific waves roiling against the rugged shore of California‘s Monterey Peninsula, Ken Derr can look north and on a clear day see as far as Santa Cruz. To the south is Carmel and Pt. Lobos. Back east, a treacherous piece of ocean and then dog-legging to the right is a 382-yard par 4 that, to Derr, is a work of unmatched splendor and an ever-changing test of golf. “I’ve had lots of birdies there and maybe that’s why I consider it my favorite hole,” says the 61-year-old chairman and CEO of the San Francisco, CA-based Chevron Corp. “But I’ve put up my share of big numbers, too. What strikes me most about the 17th is the scenery. It’s also great because it plays so different each time around.”

The sentiment captures what’s drawn Derr to a sport that’s humbling, exhilarating, “and at times can just plain drive you nuts.” A varsity tennis player at Cornell, he didn’t take up golf until the mid-1970s. “Tennis is great, but if you’ve seen one court you’ve seen them all,” he observes. “Every golf course is different and most are in gorgeous settings.”

Lured into golf by playing at business-related events, Derr got completely hooked when his wife Donna took up the sport. “About the last thing I want to talk about on a course is business,” says Derr, who has a 14 handicap and usually plays “couples golf” with Donna and their friends, and occasionally with other CEOs. “But the game does bring out the best and worst in people. After a round you’ve got a good idea if this is the kind of person you’d want to do business with.”

Cypress is among the most outstanding of Alister Mackenzie’s fabled designs. “You have a variety in the topography, in the holes, and those ocean views,” explains Derr. “From the 9th you can see most of the course and how Mackenzie made use of the natural terrain.”

Though not the most difficult hole at Cypress, the 17th is no cupcake. “The carry over the ocean isn’t bad,” says Derr, “but if you try to cut the dogleg too tight and slice, you’re in the water. From the middle of the fairway you face several big pine trees about 100 yards from the green, which can block your approach. After a good drive I like to cut a mid-iron past the left side of the tree. If I can go over the right side of the tree I’ve got a shorter shot, but that means I got lucky with a bad drive that stayed out of the ocean.”

One of Derr’s finest golf moments came at the 17th during the 1990 AT&T pro-am. “My second shot hit the tree and dropped straight down,” he recalls. “But my pro partner, Duffy Waldorf, airmailed his second into the ocean. Now he’s counting on me, and my nerves are jingling.”

Derr somehow got on, two putted, and walked off with a bogey that yielded a net par. It may have been the only time, he concedes, “that I didn’t look around and appreciate that the 17th at Cypress just might be the most beautiful spot on earth.”

Cypress Point Golf Club



Location: Pebble Beach,

Hole: 17th, par-four, 393 yards from the blue tees, 382 from the whites.

Hole Description: From an elevated tee the drive must carry an ocean inlet to a wide fairway with a dogleg right. Second shot must pass strategically located trees to an away-sloping green flanked with bunkers and ice-plant. Wind is often a factor.

Course Architect: Dr. Alister Mackenzie       

Club Description: Designed in 1928 and widely considered MacKenzie’s best work, Cypress Point is frequently ranked among the world’s top five golf courses. Sand, sea, forest, and the varied terrain of a stunning locale make Cypress a sacred temple of golf.

San Francisco-based journalist Jay Stuller writes for numerous national magazines, including Smithsonian, Senior Golfer, and Men’s Journal. 

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