Of course, Woods has played with Phil Knight, CEO of his megasponsor, Nike. But missing from the Tiger Club are CEOs of companies with strong golf connections, including ConAgra, MasterCard, Travelers, Gatorade, Coca-Cola, Verizon and Wyndham Worldwide, although Wyndham CEO Stephen Holmes gladly recounts walking with Woods at the Presidents Cup tournament in Montreal in September. "Tiger's a legend, not only in the golf community, but as a marketing phenomenon," Holmes says. "If I was invited to play a round with him? I don't know how anyone could say no."
"I've heard stories of people paying $1 million to play with him," says CEO Dan Warmenhoven, one of three Network Appliance executives and a doctor who together paid $660,000 at a charity auction to play in private with Woods in Orlando. The 2001 round was in a gated community at Woods' home in Florida. Plus, the caddy was Warren Buffett.
Buffett says Woods challenged him at the 18th hole for $5, no strokes, which caused Buffett to practically faint, partly because he considers $5 serious money. Buffett says he made good on the $5 but requested 50 cents for the caddy's 10% cut.
Warmenhoven's recollection is different. He says after Buffett rode around in the cart cracking jokes for 17 holes, Buffett challenged Woods on the 18th. Borrowing a club, Buffett hit a nice drive more than 200 yards uphill. Woods moved to the back tees, got on his knees and hit the ball 240 yards, 20 yards beyond Buffett's ball.
Buffett's second shot sliced into the lake. Warmenhoven says Buffett told Woods he wanted a mulligan, golf slang for a do-over. Woods scoffed at the request, hit a 3-wood from his knees that went 210 yards uphill and just off the green. The pitch from his knees put him 5 feet from the hole, from where he putted in from his knees for a par.
Later, Warmenhoven says he heard Buffett on his cellphone telling someone: "Tiger beat me on the 18th, but I took him to his knees." While accurate, the implication was that the two played even through 17 holes, Warmenhoven says.
Buffett says he made a funny video that day giving golf instructions to Woods. But he doesn't remember placing such a call. He agrees that he hit the ball into the lake but denies requesting a mulligan. Woods had trouble putting from his knees and did not par the hole with a 4, scoring either a 5 or a 6, Buffett says.
"Tiger wrote me a letter, saying next time he would play on his knees and blindfolded," Buffett says. "I'm not sure if that would even the match."
McNealy, one of the best golfers to have ever been a CEO, met Woods through McNealy's sister-in-law Laura Ingemanson, a friend of Woods' at Stanford University. On Labor Day weekend in 2000, she and Woods showed up unexpectedly at his door.
When McNealy told Woods that he sometimes tried to hit a distant rooftop from his backyard but had never succeeded, Woods wanted a try. Without a practice swing, he hit a drive into the late afternoon dusk. No one could see the ball, but Woods told them that it would hit about 10 yards right.
Everyone got quiet when he hit his second ball. "Kaboom! It went right off the roof," McNealy says. "He dropped the club, and we ran into my game room laughing."
Soon, Woods was asking for a third swing, and they went back outside. "Kaboom!" McNealy says. "It was an impossible distance with someone else's driver in running shoes and no practice swings. It was easily the two most amazing golf swings I've seen."