I Lost $4,000 to Wayne Gretzky's Wife on a Golf Course

The Setup

Keith Zubchevich is a Bay Area tech executive who spent years working in sales and business development, but his real credential is the Rolodex of Hall of Famers he has played golf with. Through a previous marriage and a standing weekly tee time that lasted years, Keith found himself on the course with Marcus Allen, Alonzo Mourning, Richard Dent, Ronnie Lott, and Lawrence Taylor. He has walked inside the ropes at Castle Pines with Tiger Woods, eaten lunch next to Phil Mickelson in the players’ locker room, and lost more money to Janet Gretzky than most people spend on golf in a year. He lives in Foster City, California, with his wife Jess — who happens to be a left-handed golfer who plays right-handed, hits her driver 240 yards, and once beat him straight up at Harding Park.

The Format

Keith’s golf life is built around two principles: look the part, and play with people you like. He owns over 50 pairs of Jordan golf shoes, matches his bucket hats to his outfits, and personalizes every Titleist Pro V1 with his wife’s initials. His trips range from local Bay Area rounds at Harding Park to bucket-list weekends at Pebble Beach and Spyglass Hill. Group formats are simple — automatic presses, skins, and occasional charity scramble events where he poses as the “Beat the Pro” ringer.

The Hot Takes

• Pebble Beach is worth the price — if the weather cooperates. Keith’s weekend at the Lodge with Spyglass on Saturday and Pebble on Sunday cost “crazy money” but delivered a magical experience. His wife’s only complaint on the 15th hole Sunday: “I don’t want this to end.”
• Paso Tiempo is possessed by demons. Despite looking manageable on the card, the course left Keith exhausted, frustrated, and convinced he would never return. “It doesn’t look hard, but when you’re done, you’re exhausted and you’ve shot 105.”
• Janet Gretzky will take your money. A $50 automatic press, $500 for fewest putts, and a stroke-and-a-half handicap at Sherwood resulted in a $4,000 loss. Michael Jordan reportedly refuses to play her for money. Now Keith knows why.
• Tiger Woods was just a kid — until he wasn’t. The Castle Pines International story: Keith flashed a practice pass, walked three holes inside the ropes with Tiger and Fluff, then bluffed his way into the players’ locker room for a photo that still hangs in his bedroom.
• Lawrence Taylor shoots 71-69 from the tips. At Angelus National, chain-smoking cigars and cigarettes for 36 holes with no lunch, LT played a course he had never seen before and shot 140 total.
• Look like you can play — even if you can’t. Keith’s philosophy: great Jordan shoes, cool slacks, Tiger Woods or Nike shirt, bucket hat. “If you see me in the clubhouse, I look like a player. It’s only three people who know I can’t play.”
• The two rules of golf nobody teaches you. Play with people you like, and lower your expectations. That is the entire secret to enjoying the game.

The Run-It-Back

Keith’s golf life is proof that the best stories do not always come from the lowest handicaps. They come from showing up, looking the part, and saying yes to the tee time with the Hall of Famer. For anyone planning a bucket-list trip, his advice is simple: go to Pebble Beach on a perfect weather weekend, stay at the Lodge, walk both courses, and do not — under any circumstances — bet Janet Gretzky.