(MONEY Magazine) – Discipline. Intense preparation. Experience. Mental toughness.

All the things that you need to make it as an athlete also come in handy as an investor. And lately, some of the biggest names in big-money sports have become obsessed with the stock market.

Consider: At their June mini-camp, when they weren't running button hooks or hitting tackling sleds in the sweltering Georgia heat, members of the NFL's Atlanta Falcons talked anxiously about Judge Jackson's decision ordering the breakup of Microsoft. Defensive end Pellom McDaniels assured everyone that the stock was still a good long-term hold.

About the same time, Tampa Bay Devil Rays designated hitter Jose Canseco sold his $3.5 million home in Florida. Canseco, a rabid tech investor and occasional day-trader, took about 107,000 shares of stock in a money-losing Web company called BarPoint.com as a down payment.

And late last year, Dale Earnhardt, one of NASCAR's winningest drivers, wrote a check for about $2 million. Not for a new boat or plane (he already owns a number of each) but for a seat on the New York Stock Exchange. It's a nice complement to the American Stock Exchange seat he bought a few years back.

It's not news that pro sports are big businesses, and marquee athletes increasingly consider themselves businesspeople. What's less noticed is that many superstars--as well as other athletes across the pay and fame spectrum--are also knowledgeable investors. For every clown blowing his signing bonus on a puce Bentley and a dozen gold Rolexes for his entourage, there is at least one eager student of finance who brings his laptop to practice and talks asset allocation in the locker room. The vast majority of jocks who make serious coin put most of their assets in the hands of professional money managers (some of the best of whom share their investing philosophies and picks on page 70), but the number of athletes who take an active role overseeing their investments is growing.

While some pros are willing to shoot off their mouths about, say, the presence of foreigners on New York City's No. 7 subway line, many of those we contacted--and we contacted a lot--became surprisingly quiet when the subject was investing. Among those willing to talk, we were struck by two things: the unexpected levels of their sophistication and prudence. Maybe we should have expected that; anybody who threw away a fortune on can't-miss penny stocks probably wouldn't be interested in telling us about it. Still, of the dozens of jocks we interviewed in depth, only baseball's Jose Canseco pursues an investment strategy you could call risky. Otherwise, as Gil de Ferran, a top-ranked Indy car driver told us, "I take my risks on the racetrack." De Ferran, who says he has picked up a lot from his current employer, racing legend and trucking mogul Roger Penske, generally shuns mutual funds--he hates fees and loads--but plays it safe with stocks like Home Depot and Citigroup.

None of the people here claim to be investment geniuses, although most have solid portfolios and a few, like the ex-Phoenix Suns center Mark West, are actually financial professionals (see "Pinstripes of a Different Sort," page 76). They are pursuing a variety of strategies, based on their ages, wealth and tolerance for risk--not to mention the differing economics of their sports. The profiles that follow range from mega-rich superstars who can afford the best advice money can buy to more modestly salaried athletes who, like the rest of us, focus on making the most of the money they have. But they all have cool day jobs.

SHAQUILLE O'NEAL Staying rich

Shaquille O'Neal, it will surprise no one to learn, makes a ton of money. His six-year contract with the Lakers pays him $121 million. And since leading L.A. to the NBA championship in June--and becoming MVP for both the regular season and the finals--O'Neal is in an extremely good position to negotiate an extension. Between whatever the team winds up paying him and his numerous endorsement deals, he will no doubt become even richer than he already is.

So what's O'Neal's strategy with all that cash? MONEY caught up with him on a hot, sunny day in L.A. a week after the NBA finals. He arrived at our photo shoot with all the accoutrements of celebrity: a custom car (black windows, Superman emblem on the rear bumper), a cell-phone-toting agent, and an entourage of about six rappers, actresses and others. But talking about investing, he sounded more like a C.F.A. than you might expect from a seven-foot-one, 335-pound, tattooed athlete and would-be hip-hop and movie star. "I'm very conservative," O'Neal says, "I don't like taking risks. If I have $20 million and I'm making 6%, that's okay with me. I don't need to make $20 million into $200 million."

In basketball, hot young stars, generally kids with no financial experience, are often presented with huge paychecks. For most, this is the first real money they've ever seen, and it falls on them as if out of the blue. Some learn how to handle it; others don't. Back in the 1980s, Kareem Abdul-Jabbar, one of the game's most dominant and highly paid players, lost millions via lavish spending and bad investments. O'Neal, the nba's No. 1 draft pick in 1992, says he almost fell into that trap with his first paycheck, which was for $1 million. He spent most of it on a $100,000 Mercedes-Benz with a top-of-the-line sound system for himself, a matching car for his father and an array of superstar accessories, including suits and cell phones. O'Neal knew that there was more money in the pipeline, but he was unnerved by how easy he found it to turn a lot of cash into almost nothing. So he hired business manager Lester Knispel to handle his money--with the emphasis on safety.

Knispel farms O'Neal's millions out to two money managers whose primary instructions are less to grow their client's capital than to preserve it for his two children--and their children. Knispel says he compares Shaq's portfolio with those of his other celebrity clients: If O'Neal's managers underperform their peers for two consecutive quarters, they're out. Generally, O'Neal is invested in U.S. Government bonds and blue-chip stock funds. He also owns annuities due to pay off when he's 35, 45 and 55.

All that prudence, however, doesn't mean that Shaq is unwilling to take the occasional flier on individual stocks, especially tech stocks. "The digital world is taking over," he says. O'Neal says he'll hear about a tech company--sometimes from market enthusiasts and fellow Lakers Rick Fox and John Salley--and then have Knispel look into it. Knispel says that such investments are a tiny part of O'Neal's portfolio: If a stock doesn't take off as expected within a few weeks, Knispel will dump it.

O'Neal holds a number of tech blue chips like AOL, Microsoft, Lucent and Oracle for the long haul. He also often takes equity positions in companies that he does endorsements for, such as Internet service provider Freeinternet.com and Dunk.net, an online athletic-wear store. O'Neal says he's interested in the market without being preoccupied. "I'm not the kind of guy who reads the Wall Street Journal or looks at my portfolio every day," he says. "I don't really worry about [money]. I'm blessed obviously to have it; now the thing I need to do is keep it and make it grow for my kids."

DALE EARNHARDT Racing a car is running a business

There are plenty of people in NASCAR racing who don't like Dale Earnhardt, but there aren't any who think he's dumb. Earnhardt, 49, is tied with Richard Petty for the most NASCAR Winston Cup Championships. And he's famous for playing rough. He stole a race on the final lap last autumn by bumping leader Terry Labonte at something like 190 miles an hour. Labonte lost control, and Earnhardt passed him to win. Accordingly, Earnhardt's nom de track, emblazoned on official caps, T-shirts, toy cars and countless other items, is "The Intimidator."

Sitting in his mobile home parked at the Daytona Speedway before the Pepsi 400 one rainy Saturday in July, Earnhardt seemed mild-mannered. And despite his insistence that he's just a car nut with an eighth-grade education, he speaks authoritatively about a range of investments and businesses. Some of Earnhardt's financial sophistication comes from having been immersed for most of his life in the economics of NASCAR (his late father Ralph was a champion before Dale was old enough to drive). Big money is at the heart of all pro sports, but NASCAR is refreshingly candid about it. Corporate logos are in plain view on everything from the cars to the uniforms on the pit crews. Drivers must negotiate with the team owners and the corporate sponsors whose cash makes the cars go. Agents are still rare. Most drivers make all their own deals, and tough guys of the old school like Earnhardt would sooner die than give a percentage of their take to some guy in a suit.

NASCAR winners make a lot of money, but drivers generally don't encounter enormous, sudden wealth. "We deal with a little less money at one time than a football player or basketball player who might get a $20 million contract for two or three years," he says. When Earnhardt was a rookie 21 years ago, he got a $60,000 salary from the owner of the team he raced for, plus a share of any of the purses he won. As he started winning, his salary and share of the purses went up. Product endorsements began to come his way. His face has been on the Wheaties box. Now, if you want to put a sticker on his car with your company's name on it, prices start at $1 million.

He and his third wife Teresa ("I've been down the aisle three times but only married once") manage a business empire that includes two racing teams (sons Dale Jr. and Kerry both drive for him), a Chevrolet dealership, a North Carolina chicken and cattle farm and an air transport company, not to mention real estate and securities.

Earnhardt's most unusual investments, though, are his stock exchange seats. The idea, he says, came from his adviser at Salomon Smith Barney. Earnhardt bought his Amex seat about four years ago and closed on his NYSE seat in December for about $2 million. "I think the bid is at one eight right now and the ask is two five," he says. Earnhardt rents their use back to SSB. But he regards them as long-term, dividend-paying investments, so fluctuations in price don't bother him. "It's like owning a big house and then leasing it," he says, "except you don't have to put a new roof on it."

Individual stocks that currently have his attention include General Motors (primary sponsor of the No. 3 Monte Carlo he drives) and Goodyear, as well as a number of tech issues. In the amount of time Earnhardt spends watching the market, he's different from some of nascar's other top names. These guys are businessmen too, but as far as stocks go, they're dabblers. Jeff Gordon, for instance, told MONEY he got a small piece of the Krispy Kreme IPO, and Dale Jarrett says he's made money on DoubleClick. Earnhardt names Sports Image, a maker of NASCAR shirts, hats and other souvenirs, as his best investment. He bought the firm in 1995 for $6 million and sold it a year later for $25 million to another apparel company, the publicly traded Action Performance. And his worst? "Well," he says, "I bought a damn truck one time..."

JIM COURIER From baseline to bottom line

There's something about tennis that makes you think these people ought to be financially astute. Maybe it's the sport's image as the game of patricians, brokers talking money over doubles at the club. But retired men's champion Jim Courier, 30, the possessor of four Grand Slam titles, learned about investing by doing it himself. Courier has had a portfolio since he was 19, and he manages about half of his money on his own. (Goldman Sachs runs the rest.)

Even before Courier was on top of the tennis world--he was No. 1 in the world for 58 weeks in the early 1990s--he knew his earnings peak would be in his twenties. So he became an investor back in 1989, one year after joining the tour. First he focused on mutual funds like Vanguard Windsor II. Now a CNBC devotee, he peppers his conversations with stock symbols rather than company names. "My strategy is that I would like my grandchildren to be selling my stocks," he says. Courier says he owns about 40 stocks, Hewlett-Packard and Intel among them. "My best pick was probably Sun Microsystems, which I bought in early 1994 and is now my top holding," he says. The stock has risen 5,000% and split four times since his investment. Not all have been winners, though. Courier got into Toys R Us at $27 a share in 1995. "Someone told me to buy the stock, but it's turned out to be my worst ever. I sold it at $20 a year later."

Courier has also gotten in on what he hopes will be the next big thing: broadband. "I like it long term as the demand for video content on the Web continues to grow. The need for speed is a big trend. One of these companies, like a JDS Uniphase, could become the next Microsoft or Intel. That's what I'm hoping for, anyway." He's also hoping to cash in on a forthcoming bandwidth play. Courier says that he's "pretty pumped" that his broker at Goldman Sachs has offered him a small piece of an upcoming broadband IPO--Telergy, which filed its S-1 back in May--at the offering price.

INGER MILLER On the right track

Olympic sprinter Inger Miller's current ambition lies in, shall we say, the precious-metals market. She brought back gold from Atlanta in 1996 in the 4 x 100-meter relay, and as America's No. 2 woman in the 100- and 200-meter dashes, she's hoping to pick up more in Sydney. But she's relying heavily on the stock market to get her to another key finish line: retirement by age 35.

At 28, that may seem like a tall order, especially considering her sport. "It's not like being a professional baseball player or a football player," she says. "The millions aren't rolling in each year." But appearance fees and endorsement contracts from the likes of Reebok and Adidas are changing the economics of the sport, and track-and-field athletes of Miller's caliber can make considerable amounts of money.

Influenced by her thrifty dad (a two-time Olympic medalist in the 100-meter sprint), Miller sat down, right out of college, with a financial adviser to create a 10-year plan and a longer-term plan, both of which consisted of high-, moderate-and low-risk investments. The low-risk category includes her IRA (mostly index funds). The moderate category is made up of diversified mutual funds that her consultant has recommended. And the high-risk sector is for stocks, the area where Miller gets most involved.

Miller is a disciple of the Peter Lynch school of stock picking: Buy what you know. And, of course, Miller knows track. Her first buy six years ago was Nike, which she has never sold. And earlier this year, when she learned that a young company named Quokka Sports was teaming up with NBC to broadcast the Sydney Games live on the Internet, she bought the stock, which has been on a steady rise in the past few months. Beyond sports, she's purchased DaimlerChrysler, in part because of her passion for Mercedes cars. Now Miller's thinking about opening her own E*Trade account so she can experiment more. "At this age, this is when you can take some chances," she says.

JOSE CANSECO Swinging for the fences

Perhaps no pro athlete is more market-obsessed than Tampa Bay Devil Rays designated hitter Jose Canseco. Glued to CNBC, Canseco checks his portfolio so often (he says he has 90% of his assets in the market) that his business partner Walter Sollie has trouble getting him to return e-mail messages.

Canseco says his interest was originally born of boredom. "I got interested just by reading certain books about mutual funds, reading MONEY magazine, anything I could get my hands on, because our flights are so long and so tedious." Recently, though, Canseco has started his own company (run day to day by Sollie, a former loan officer) called Canseco Financial Group. The outfit started as a mortgage lender--its target audience is baseball players who want homes near spring-training fields in Florida--but Canseco and Sollie hope to turn it into an investment vehicle for rich athletes.

As far as his own stocks go, Canseco says he is overwhelmingly into tech stocks, including big names like Yahoo! and AOL. He also likes pharmaceutical maker Immunex and Internet company Chinadotcom. And he recently sold his Florida home to one of the founders of BarPoint.com, an online comparative-shopping service portal, taking the $1.5 million down payment in stock.

Canseco's attitude toward investment is not for the faint of heart. "I spoke to a number of players last year, when I believe anybody could have made 100%, and I asked: 'How much money did you make in the stock market last year?'" he says. "Guys said they made 30% or 40%, and they thought that was good. And I'm thinking, 'You made only 30%, 40%, when the average person was making 80%? What are you going to make when the market is down?'"

Canseco says that he's not worried about the risks he's taking. But perhaps his risk tolerance is different than most people's. He is, after all, a specialist in a field with a high failure rate. As a designated hitter, his sole job is getting hits--and the more of them that are home runs, the better. But most big home-run hitters also strike out a lot. Over 15 years in the majors, Canseco is a career .267 hitter, with 6,648 at-bats, 439 home runs--and 1,816 strikeouts.

LISA LESLIE AND ALLISON FEASTER Not about the money

The average salary in the NBA is $3.5 million. The NFL's, at the low end of the major men's sports (yes, lower than hockey's), stands at $1 million. But in the WNBA, salaries average $55,000. If there's a group of athletes who need to nurture their portfolios, it's the women of pro basketball.

"There's only a handful of us who make enough to invest," says Lisa Leslie, the L.A. Sparks center who is one the league's few superstars. "You're talking maybe 10 players at most who have enough to put away and still help take care of their family." Since Leslie is one of those fortunate few, she's become more involved in her investments, which are managed day to day by a cousin who's a broker. That's why she's lately been chatting up her teammate Allison Feaster, an active investor and aspiring Wall Streeter. When Feaster was drafted by the Sparks upon her graduation from Harvard in 1998, she turned down a job offer to become a securities analyst at Merrill Lynch.

Because of her modest salary, Feaster knows much is riding on her investments. "I'm not wealthy, so I have to pick and choose," she says. "I don't take a lot of chances." While she's heavily invested in tech stocks, most are blue chips such as Oracle, Nokia and AOL. She estimates that her portfolio is 50% stocks, 40% mutual funds and 10% cash. She also takes advantage of the WNBA's 401(k). The league matches 25% of players' contributions.

Feaster says that she's a buy-and-hold kind of gal--most of the time. Earlier this year, about a month prior to 3Com spinning off its Palm unit, Feaster got in at around $56. Over the following month, her stake doubled. "The day Palm went public," she says, "I had to go to practice, and I didn't want to sell 3Com too late, so I decided to sell before I went to practice, at $108." Her timing couldn't have been better. The stock peaked at $117 that day and fell as low as $40 four weeks later.

Leslie, meanwhile, has also been courting advice from Charlotte Sting player Dawn Staley, who, Leslie says, is hot on pharmaceuticals right now. And Leslie is all ears. "When it comes to money," she says, "I have to understand. I think it's important to educate ourselves."

SERGEI FEDOROV AND LUC ROBITAILLE Hockey gets smart

Sports money manager Frank Zecca says that his hockey clients used to be financial bumpkins. Now he gets calls from wised-up ex-bumpkins asking detailed questions about stocks he's never heard of. One of his clients is Russian-born Detroit Red Wings star Sergei Fedorov, who's been in the West only nine years. But you wouldn't guess that from hearing him talk investments. "When I came over, it was 1991, and I had no idea about any of this," he says in flawless English. Fedorov has since had good reason to learn. In 1998, he signed a six-year, $38 million deal with the Red Wings.

Upon arriving in the U.S., he put his first bonus check into bank CDs, then migrated into Treasury bills, Michigan municipal bonds and a variety of mutual funds. He also maintains a small brokerage account on the side with which he dabbles in tech stocks and other short-term holds. He says, "I have money to fool around with. Sometimes I'll come to the office and say, 'Let's invest $10,000 in the red area and see what we can do in a week.' If I lose, I lose; and if I win, it's better than playing a casino." Fedorov's holdings currently include two stocks he loves, Nokia and Dell. "I personally have three Nokia phones and I use them every day, and my parents use them and my brother uses them. Nokia came out with something that everybody can use. It's a no-brainer."

The biggest positions in his portfolio, which is managed for him by pros overseen by Zecca, include Cisco, GE, Wal-Mart, Johnson & Johnson and ExxonMobil. He also owns Microsoft, about which he is guardedly optimistic. "I didn't sell it because I'm sure it's going to come back once everything settles down," he says.

Fedorov is not the only hockey player who knows the difference between a hat trick and a three-bagger. Luc Robitaille, a left-winger for the Los Angeles Kings and one of only 20 players in NHL history to score more than 550 goals, has recently been building a slightly racier blend of stocks than he's used to. His portfolio--traditionally a fifty-fifty mix between stocks and bonds--is now 70% equities. While most of his investments are of the "Coca-Cola or Gillette nature," he also owns shares of Ericsson and Qualcomm, stocks he follows on his wireless Palm VII. "It's so cool," he says of the gadget. What's not so cool, he adds, is Qualcomm in 2000. After its gigantic run in 1999, Qualcomm is now trading around $62, way off its December 1999 high of $200. "I'm not sure what to do with that stock these days," he says. "I've lost most of my gains."

Some of Robitaille's best performers have been tips from friends or teammates. And what may have been his best pick came, in a way, from Kings owner Philip Anschutz. "A bunch of us bought Qwest after Anschutz took over the team," he says. Anschutz is chairman of Qwest, a Colorado-based telecommunications company that recently acquired U S West. "We figured Anschutz doesn't miss a lot of boats, so we didn't want to miss this one." Robitaille bought Qwest shortly after its 1997 IPO; since then it has risen more than 600%.

A 13-year veteran of the NHL, Robitaille has witnessed firsthand the changes taking place among professional athletes and their interest in finances. Suddenly, he says, the Kings roster is filled with stock junkies. "Nobody used to talk about stocks 10 years ago," he says. "Now that's all they talk about. Someone always has a great scoop, whether it's in the locker room or before practice drills. We talk stocks every day but game day."