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That night we had the rare treat of dining in the Cypress Point clubhouse, which is somehow both elegant and informal. There was a rush at the bar for the famed Sam's Special—a fizzy, blended rum drink that is dangerously delicious. I was excited to be seated at Ueberroth's table for dinner. He's known to most folks as the former baseball commissioner and TIME's 1984 Man of the Year for his stewardship of the Los Angeles Olympics, but in my part of the world he is celebrated as the most influential managing partner of the Pebble Beach Company. Over dinner Ueberroth confirmed my long-standing belief that raising the $820 million needed to buy the company in 1999 basically boiled down to calling his Swallows buddies and asking each of them to kick in a few million dollars' worth of loose change. "It's because of the people in this room that the deal got done," he said.
Talking about business is subtly discouraged at the Swallows, so the conversation centered on Tiger Woods's travails and the upcoming U.S. Open. For the latter topic, it was helpful to have at the table venture capitalist Geoff Yang, whose impeccable golf résumé includes memberships at Cypress and Augusta National and a spot on the USGA executive committee. Interestingly, Ueberroth was most animated when he discovered that my lineup of kids consists of three girls and a boy as the youngest, which is the same as his own brood. "I can tell you everything that's going to happen to you in the next 20 years," he chortled. I refrained from inquiring whether that would include future Swallows invitations.
The second day of golf brought a spin around Pebble Beach, which was shut down for the day to outside play. C.O.D. and I continued our disconcerting tendency of blowing up on the same hole, and we mustered a round of only one under par, dooming us to a middling finish. But it turns out that most of the guys at the Swallows don't really care about their score, more or less by design.
The winning and second-place teams get gorgeous bronze trophies and a cash stipend, but that's it as far as prizes go. Since third place and 46th place pay the same, there is a notable absence of grinding, so the golf is fun and relaxed.
The morning shotgun was followed by a cookout at a house owned by the Pebble Beach Company on the 1st fairway. Then came the most cherished part of the Swallows: an afternoon during which Pebble is a private playpen, and anything goes. (Last year O'Donnell crammed in 54 holes, the final 18 a Zen round all by himself played in under an hour.) I wound up in a twelvesome that raced to the 3rd hole to jump ahead of the other marauding golfers. Joe Mayernik, a Cincinnati raconteur, showed up on the tee with a case of Silver Oak cabernet, which retails at the Pebble Beach Market for $85 a bottle. It was gulped at a rate of about one bottle a hole. For our game, each guy kicked in $50—I can expense that, right?—and we were paired in two-man teams. Jerry Yang and Geoff Yang are not related, but they turned out to be a formidable duo of trash talkers. They routinely credited their good shots to "a thousand years of superior breeding." On each hole partners had to "simul-blast," teeing off at the same time as everyone else hooted and hollered a 3-2-1 countdown, a stressful scenario that wreaked havoc with my tempo. Each hole was played with a different format: alternate shot, better-ball, etc. For the diabolical par-5 14th a worse-ball scramble was in effect. When Mayernik's partner, Davis Sezna, foozled a shot into a fairway bunker, someone shouted, "They're leaking cab!"
After 12 strokes Mayernik and Sezna still hadn't reached the putting surface, and a mercy rule was invoked, allowing them to pick up. This sloppy, giddy afternoon at the Beach was probably the most fun I've had on a golf course.
The golf concluded the next day at Spyglass Hill, the third round in a row with absolutely perfect weather, and then everyone jumped in their jets and winged home. But first there was one last steak dinner, on the preceding night, and for me it was a highlight.
George Roberts was seated next to me. He's a soft-spoken guy with a gentle manner who offers no hint that he's worth $3.8 billion. We talked about golf—what else? For both of us it's a favorite topic, and the chitchat served as another reminder that at its core, the Swallows is simply a gathering of guys who love the game.
It is a Swallows tradition to have an open microphone at the final dinner for storytelling and occasional blue humor. There is also a history of hazing the rookies. First-timer Jackson Hsieh, global head of real estate investment banking at UBS, was called to the front of the room and asked to sing the fight song of his alma mater, Cal. He was barely on the second line when he was booed off the microphone.
Residing as master of ceremonies was Paul Spengler, a majordomo in the local golf scene. Spengler helps vet the list of the invitees for both the Swallows and the Pebble Beach National Pro-Am, making him more powerful than many senators. When I was a cart boy, he was an executive overseeing Pebble Beach Company's golf operations and therefore my de facto boss. I was squirming in my seat throughout dinner, knowing that Spengler was going to single me out. But first he called up Danny Sullivan, who gave a detailed recounting of his famous spinout during his victory at the 1985 Indy 500. Next to speak was Tom Siebel, a Swallows regular who couldn't play this year because he's recuperating from severe injuries suffered when he was stomped and gored by an elephant while on a safari in Tanzania. He offered a harrowing recounting of the attack. Finally, Spengler called me up. I couldn't match Sullivan or Siebel for drama, and there was no use trying to be funny, because I knew the next guy on the mike was going to be Sezna, a legendary joke teller. So I went for sincerity, explaining how meaningful it was for me to have gone from a lowly cart boy to playing in the Swallows.