The Long Shot Tiger Woods may be great at golf, but his timing in business could use some work. Can the greatest name in sports survive a stumbling economy?

Tiger Woods, dressed for a crisp autumn day, walks confidently down an uneven slope among trees ablaze with fall colors at their peak. High in the Blue Ridge Mountains outside Asheville, North Carolina, he stops at a white pole that marks the site of what will be the 18th green of his first golf course in the United States. Earlier, a helicopter whisked him from his private plane to this isolated mountaintop, where he is about to shovel some ceremonial dirt. The course itself won't open for at least two years-probably a good thing given the dismal state of the economy, which has led to the worst golf market in decades.

Yet Woods is all smiles in front of a select crowd. He faces a clutch of photographers, public relations people, and developers, as well as a select group of buyers who would later admit that this moment, this chance to spend time with Woods, was what lured them into the deal in the first place. (View a slideshow about other top athletes going into business.)

"Okay, left foot on the shovel," a photographer shouts, focusing the crowd's attention on Woods' left knee, which is still questionable from surgery. Woods' career, and possibly the success of this particular patch of dirt, hinges on that knee. If it heals sufficiently, he'll be able to continue playing at the top of his game, building his legend and thereby increasing the allure of his courses. If not, his marketability will take a ding.

On cue, Woods pushes his left foot down onto the shovel and loosens some dirt. He flicks it forward and flashes a cheesy grin. He switches to his stronger leg and digs two more times, then grips the shovel like a golf club and mugs for the camera. Finally, Woods hands the shovel to an assistant, shakes a few hands, and slides into the Range Rover that will shuttle him to his next commitment.

Woods sketched his first golf course when he was 11. Twenty years later, he founded Tiger Woods Design, which is handling the project in North Carolina. "I don't do anything quickly," Woods tells me when we sit down in the clubhouse of a nearby course designed by Jack Nicklaus, the golfer to whom Woods is most often compared. "I think through it. That's one of the attributes I think that golf has allowed me to learn."

The course near Asheville is one of three that Woods has under contract. The design and marketing efforts for those courses give the first indication of what his eventual post-pro-golf career may look like, in addition to his exceedingly lucrative endorsement business. "I made a note that I wanted to play all around the world before I got into the business," he says. "I've played every different style of golf course you could possibly imagine."

What Woods is now undertaking is on a scale unlike anything that he or any other athlete has attempted before. Uncharacteristically, his timing is terrible. He is entering the real estate business just as the economy seems moribund-and if anything, the golf business is in a worse state. The National Golf Foundation, an industry trade group, reported that 2008 was the worst year in two decades for opening new golf courses, with the sluggish real estate market as the leading negative factor. It also noted that 2008 was the third year in a row with "zero to slightly negative net growth in supply"-meaning that more courses went out of business than opened.

Home prices in Hilton Head, South Carolina-among the country's top golf getaways-fell 10 percent in October, while the number of rounds of golf played there fell between 5 and 20 percent.

But Woods isn't designing courses at Hilton Head or anywhere near it. His first course in the U.S. will be in the high-end project outside Asheville, the eighth development by Cliffs Communities. He is also designing Punta Brava, a course in Mexico. And his course in Dubai is expected to open later this year, even as declining oil prices have caused a real estate slump there too. All three were conceived in better days but are now sprouting amid massive economic shifts.

For Woods, the collapse of the global golf economy is nothing more than a bad break. Neither he nor his backers will be drawn into hand-wringing over the state of their ventures. But the economic pressures have nevertheless injected an unexpected element of uncertainty into Woods' business plans, which have shifted from a sure thing to a riskier bet.

Even Nicklaus, an admirer of Woods' talent on the course, is skeptical about the new projects' timing. "He's on his third golf course contract," Nicklaus says, emphasizing the last word. "He hasn't done any yet. I don't think he's finished any golf courses."

It's always foolish to bet against Woods, who won the U.S. Open in June despite two stress fractures and a torn ligament in his leg, solidifying his status as a sports legend. And in the short term, Woods stands to gain no matter what happens to these projects. While precise numbers are a closely guarded secret, Golf World estimates that for Punta Brava alone, Woods' firm will be paid $25 million. If that figure is even close to correct, it is unprecedented, given that a backer of one of the courses puts the cost of the entire Punta Brava venture at about $100 million. Top course architects like Tom Fazio rarely earn fees of more than $2 million.

When Nicklaus opened his first golf course, Glen Abbey, in Oakville, Ontario, at age 36, the difference between his earnings on and off the course was not so great. Today, Woods' growing business interests account for seven times his winnings on the PGA Tour. In addition to owning Tiger Woods Design, he is paid to endorse Accenture, Electronic Arts, Gatorade, Gillette, and Nike. In all, he earned $769 million between 1996 and 2007, according to Golf Digest. Only $100 million of that came directly from playing golf.

On the course, Woods has a reputation for beating his opponents before they even tee off. His very presence has a ripple effect that unsettles the rest of the field. An economist at the Kellogg School of Management at Northwestern University has shown that when Woods competes, other golfers in the tournament shoot nearly a stroke higher-a remarkable statistic considering that the difference between the second-ranked player on the PGA Tour and the lowest-ranked member, No. 125, is only two strokes.

Woods seems to have a similar effect on investors in his golf courses. When doing business with Woods, many of them suspend their normal skepticism. Red McCombs, a Texan who made his fortune with some 50 car dealerships before co-founding radio giant Clear Channel Communications, is a backer of Woods' new venture in Mexico.

McCombs, 81, whose net worth is estimated at $1.7 billion, is not one to swoon, but the prospect of working with Woods was tantalizing. When Punta Brava's developers approached him seeking an investment, McCombs was initially reluctant. "I wasn't turned on by the whole thing," McCombs says. "Then they said, 'I think we can get Tiger involved in designing this.' I said, 'Forget it. It's over. I'm in.'?" Woods, he adds, "has such an impeccable background."

The developers of the Cliffs project near Asheville were similarly starstruck. Jim Anthony, founder of the privately held Cliffs Communities, says that he would not have even included a golf course at the Asheville development if Woods hadn't agreed to design it. After Woods announced his intentions to design his first course, at a resort in Dubai, Anthony reached out to him through Beau Welling, who built two courses at the Cliffs for Fazio and was the lead designer for Tiger Woods Design. "I said, 'Let's get Tiger,'?" Anthony says. "He knew what an incredible property it was. Beau said he'd try to set up a meeting with Tiger."

Even Daniel Brazinski, the burly vice president of golf course construction for the Cliffs, gushes about meeting Woods. "I was tongue-tied the first time we met," he says. "After an hour, he realized that and just gave me a hard time about it. Now we get along great."

For his part, Woods and his advisers know that it's critical to the golfer's business reputation that these deals work. "We don't sign contracts right away," Woods says. "We're in this together, through thick and thin."

At age 33, Tiger Woods is the biggest sports star on the planet, eclipsing even David Beckham in global renown. Like Barack Obama or Madonna, he is one of the few people who are recognized anywhere. His time is doled out as deliberately as dollops of beluga caviar. Woods' golf course backers know this, and they are hoping that his iconic power will boost club memberships and home sales. In short, they are hoping that Woods can do for them what he did for Nike.

When the sporting-goods company signed Woods in 1996, it didn't even make golf clubs or golf balls. Still, Woods earned $40 million. Two years later, Nike started a golf-equipment division. Then, in 2000, the company introduced a golf ball that Woods was willing to use full-time in competition. He was rewarded for his support with a reported $100 million for an additional five years-a record-setting endorsement deal for Nike.

With Woods' help, Nike's golf division has gone from zero to an estimated $600 million in annual sales for 2007, ranked fourth behind Acushnet (the parent of Titleist), TaylorMade-Adidas, and Callaway Golf. Unlike most of the other athletes Nike has signed, Woods receives a percentage of sales, so his interests are aligned with the company's. "I've not gone necessarily into endorsements per se but into building a brand and having ownership in some of them," Woods tells me.

That, however, is not the way he has structured his golf-course-design deals. Woods is earning a flat fee to design and promote the courses. That money will be paid regardless of whether the associated real estate deals survive the economic downturn.

The setup is remarkably risky for investors, given that Woods has never completed a course design and that all the projects have built-in knocks-from out-of-the-way locations to high costs. But Woods shows no signs that he's daunted. "I've learned so much in these few months," he says. "The amount of meetings I've been in-you'd be shocked by the number of meetings I've been in, but that's how you gain the knowledge: being in the meetings and participating. You learn and you grow."

The two-year-old company Woods has created is run by people loyal to him. Its president, Bryon Bell, is one of Woods' oldest friends. The pair have known each other since seventh grade. Woods hired Bell as operations director at his foundation seven years ago and put him in charge of the design company when it launched in November 2006. "My job is to help Tiger execute his vision," Bell says. "We probably get 20 to 30 legitimate opportunities each month. I spend a lot of time going to these sites and finding the right owner."

Trained as an engineer, Bell is an average golfer with no experience running a global design firm, but he has worked for Woods for most of his career. In 1999, the golfer, struggling with his game, asked Bell to caddy for him at the Buick Invitational. Bell had caddied for Woods before, at the U.S. Amateur in 1996. This time, Woods' selecting him was meant to send a message to his regular caddy, Mike "Fluff" Cowan, a big man with a walrus mustache who had been carrying Woods' bag since he turned pro. But Cowan had begun capitalizing on his association with Woods to endorse products, much to the pro golfer's chagrin. A few weeks after the Buick, Woods fired Cowan and hired a new, more discreet caddy.

Bell is Robin to Woods' Batman, and he's clearly comfortable in the role. But with limited knowledge of course design, Bell sticks to running the business. Beau Welling oversees course design.

Woods recently hired Glenn Greenspan to handle his public relations. Little known outside the golf world, Greenspan is regarded as the ultimate pit bull by golf insiders. For the previous 12 years, he worked as the director of communications for the Augusta National Golf Club, which hosts the Masters, where he shut down a media storm over a campaign to admit women as members.

"Tiger's well advised," says Bill Woodson, managing director and head of family-wealth planning at Credit Suisse. "If you can hire the right people, they'll take on these responsibilities and do it well. You can stay focused on what you're doing."

Yet the Cliffs and Punta Brava people I spoke to have been surprised by how involved Woods has been. "I don't think I expected the intensity," Cliffs V.P. Brazinski says. "When Tiger shows up, he puts on his boots, gets a bottle of water, and says, 'Let's go.' When some of the other designers come, they just want to see it by helicopter."

McCombs had a similar experience in dealing with Woods on Punta Brava. "He has spent three times as much time on the property as I have," McCombs says. "He was interested in far more than just putting his name on it."

What is now the 12th hole at Punta Brava, a beautiful expanse along the Pacific Ocean, was originally slated to become a cluster of prime homesites. "Tiger said no way," McCombs says. "He was absolutely right. Structurally, it was the right decision."

Woods has been planning his new courses for the past two years. His managers at IMG began brokering the deal for the project in Dubai in 2006. In December of that year, a month after taking the helm of Tiger Woods Design, Bell was approached by Punta Brava backers about involving Woods in the project. Bell toured the site in January 2007 but took another year to commit. A few months later, in April 2007, Woods was approached by the Cliffs team.

With Woods now ramping up his work off the links, some golf fans are concerned that his game will suffer. The history of professional sports is littered with players who have lost focus while pursuing riches. "All that money that comes from sports comes in quickly, and it goes out just as quickly," says George Foreman, the heavyweight boxing champion turned entrepreneur. "I don't care if they sign you for $100 million-that's just your start into business. That's not your nest egg. You could lose that in a second."

Foreman, who says he admires Woods, retired in 1977 at age 28 and thought he was set for life. Ten years later, out of shape and nearly broke, he was forced to return to the ring to raise money. "I went back into boxing the second time just for business," he says.

In 1993, a year before he regained the heavyweight title, Foreman was contacted by the appliance maker Salton, which asked him to serve as its pitchman for a new grill. "They said, 'We don't have any money,' so they gave me 45 percent of the thing," Foreman says. In 1999, Salton bought out Foreman's stake in the George Foreman Lean, Mean, Fat-Reducing Grilling Machine, paying him a reported $127.5 million, plus $10 million in stock for the right to use his name and image in perpetuity.

Woods emphasizes that he is going to design, as he puts it, a limited collection of courses. He will not put a number on how many, but the implication is that it will be fewer than Nicklaus' 337. This may be an acknowledgment that Woods realizes he can't commit to designing a dozen courses a year while continuing to play golf at the highest level.

A couple of days after winning the 2008 U.S. Open, with much of the sports world focused on the state of his knee, Woods was in Mexico to vet Punta Brava's new layout for the 22nd time-more than five times as many site visits as most brand-name golf course architects do.

Woods limped across the slick rocks to the 17th tee, the Pacific Ocean spraying up around him. Once he made it across, he could survey what he had been looking for: a stunning piece of land with a peak in the background and water all around.

Brady Oman, one of McCombs' partners, says that Woods stayed at the site of the future golf course for three and a half hours. "I was either next to him or behind him the whole time. His knee was buckling. He would twist and turn, and it would sound like a toolbox," Oman says. "After about two and a half hours of this, I turned to Tiger and said, 'We don't have to keep walking this. We can get into a Suburban.' He said, 'The hell with it. I'll get it fixed.'?"

After walking the course and shooting a video for potential home buyers, Woods left Punta Brava. He flew directly to Park City, Utah, and early the next morning underwent the knee surgery that has sidelined him ever since.

"I have to shield him, but I don't have to shield him so he can maintain his focus," Mark Steinberg, his longtime agent, says.

If Woods wants to keep his business partners happy, he will also have to help sell the high-end homes that surround his planned courses. Punta Brava is aiming to be ultra-exclusive, with an international clientele. The entry-level price for one of its 90 homes is expected to be $3.5 million; the most expensive site is $12 million. The golf club will have fewer than 400 members, including the 240 people who are expected to pony up $1.6 million for 90 days of fractional ownership in one of 60 villas. And if you don't have your own plane, getting to Punta Brava will be tough.

For Woods, the most draining part of his new ventures may be knowing that their success or failure depends entirely on his image. Watching Woods at a marketing event for Punta Brava at the Hotel Bel-Air in Los Angeles, I remembered a story I'd heard about a network newscaster whose family jokes that they have to roll out the "show pony" whenever someone wants to meet him.

Woods is the show pony. No one at the Bel-Air would be especially interested in paying $12 million for a homesite in the middle of nowhere in Mexico on its own merits, but the chance to buy into a club associated with Woods is another matter. That's why the developer of Punta Brava stresses that Woods will have a home there. The Cliffs' developer touts the same claim. (Woods' representatives say that details of those arrangements have yet to be worked out.)

"I introduced him to every single person at lunch," Oman says. "Then he went into the press conference and did one-on-one interviews afterward. I had a V.I.P. reception in my suite at 6:30, and then he went into the reception at 7:15. I introduced him to every single person that night-250 people. It went past midnight. He stayed way past the end."

Midway through that day, I watched Woods walking alone past the hotel's outdoor bar. For a rare moment, the guests were too wrapped up in their own conversations to notice him. He looked lost in thought. His expression was somewhere between pained and distracted. In an instant, he collected himself. He smoothed his jacket, touched his temple, and kept moving.

At the end of the night, a Bentley Continental GT pulled up to the valet stand. As its owner climbed in, he called back to the attendant, "It's not every day you get to meet Tiger Woods."

Right now, several hundred million dollars is riding on whether that sentiment will translate into home sales.