(MONEY Magazine) – George W. Bush, one of the richest presidential candidates in history, is described by his closest friends as a cheapskate. Albert Gore, who's cultivated a reputation as someone uninterested in the pursuit of money, can afford not to worry: He stands to inherit millions from his and his wife's families.

These are just two of the surprising details we've unearthed in an extensive look at the candidates' personal finances. We've interviewed dozens of people who know them well--from childhood friends to personal accountants, from relatives to political aides. And we've scoured their financial disclosure documents, including years of tax returns. What emerges from all of this is an intriguing picture of how the candidates got to be so well heeled, how they spend their cash and how they invest it. None of this is likely to influence how you vote--but it does tell you a great deal about who they are as people.

As in politics, Bush and Gore have strikingly different styles when it comes to money. Gore doesn't own a single stock, while Bush has invested in a slew of blue chips. Bush's portfolio is highly diversified (he even owns a stake in a dry-cleaning firm), whereas Gore's assets are almost all in real estate. Gore has no funds, no blind trusts, no financial advisers. Bush has all three.

Still, the rivals do have one thing in common. As the sons of politicians, both grew up around money and power. They understand how these two things are intertwined--and have cashed in on that to make themselves wealthy. Indeed, Bush owes much of his business success to his impeccable connections: Family friends, prep school buddies and college fraternity brothers have all been key investors in his various business ventures. As for Gore, he's benefited richly from his father's financial savvy and was even his partner in a number of deals.

In short, both men are sons of privilege. "They are not average Americans," says Peter Eisner of the Center for Public Integrity, a nonpartisan group that tracks their business dealings. As Eisner puts it, "Gore is to the manor born. And Bush is to the manor born more."

PRIVILEGE PAYS GEORGE W. BUSH

The 54-year-old Texan is known among his friends for his biting sense of humor and his willingness to direct it against himself. And throughout the 1980s--as energy prices sank and his oil drilling venture faltered--Bush used to joke that he was all name, no money.

Since then, however, he's managed to turn that name, and the connections that go with it, into money. Big money. In his latest financial disclosures, Bush pegged his family's net worth at $11.1 million to $29.4 million. By our conservative estimates, he's worth at least $20 million, making him one of the richest presidential candidates in decades. In 1998 alone he earned more than $18 million, mostly from his investment in the Texas Rangers baseball team.

Bush was always eager to get rich, but not because he craved fancy cars, chic clothes or flashy restaurants. In fact, friends uniformly describe him as a penny pincher who, in the words of childhood buddy Charles Younger, "would rather have you buy his dinner than vice versa." Younger, now a surgeon, recalls how delighted Bush was when they once got into a Willie Nelson concert for free because Younger knew the band's drummer: "George loved having fun, and he loved anything that was free." Clay Johnson, who went to Andover and Yale with Bush and is now his Chief of Staff, says he "keeps the same friends and the same clothes for 30 years." And campaign spokesman Dan Bartlett adds: "He can go for months wearing the same jacket."

What's driven Bush's pursuit of riches is apparently one of the same forces that propels his political ambitions: his complex relationship with his father, ex-President George Bush. As one political pundit explains, "Making money is considered a measure of manhood in the Bush family." Bush Sr. struck it rich in oil in the 1940s before running for public office; his father, Prescott Bush, was a wealthy Wall Street financier before entering Congress; and Prescott's father got rich off steel and railroads.

So it's no surprise that George W. Bush went to Harvard Business School and, in 1977, launched his own oil firm, Arbusto Energy. Setting a lifelong pattern, he received invaluable help from friends and family. His uncle, Jonathan Bush, assembled a group that invested $3 million in the fledgling company. These backers included loyal political supporters of Bush's father, such as venture capitalist William Draper III.

The firm, which was later renamed Bush Exploration, fared poorly. "George was a low risk taker," says Younger, who invested in it and says he made a little money. "He didn't do wildcat wells that have high risks and also potentially high returns. He did more drilling around known production sites. In the oil business, it's better to be lucky than smart, and George wasn't all that lucky."

Still, friends came to the rescue. In 1984, Bush's ailing firm merged with Spectrum 7 Energy Corp., which was co-owned by William DeWitt, a family friend. Bush was appointed CEO of Spectrum and given a $75,000 salary and 1.1 million shares of company stock. By 1986, though, Spectrum was nearly broke, because of the plunging price of oil. Bush was saved when Spectrum was acquired by Harken Oil & Gas, a publicly traded oil exploration outfit. He got $600,000 worth of Harken stock and a six-figure consulting gig with the firm.

It wasn't long before another enticing deal came along. While working at Harken, Bush got a call from DeWitt, his ex-partner at Spectrum, saying that the Texas Rangers team was up for sale. Bush helped to assemble a group of investors who bought the team for $86 million in 1989. Bush himself invested $500,000, borrowing the money from a bank in Midland, Texas where he had previously been a director. (He later put in another $106,000.)

Bush cashed in most of his shares in Harken in 1990 for $848,000 and paid off his loan. It was a well-timed sale. Two months later, Harken posted a hefty loss and the stock tanked. The Securities and Exchange Commission investigated to see if Bush had traded on inside information that he might have obtained as a director. But the investigation was closed in 1991 with no action against him.

The Rangers deal worked out beautifully. In 1998 the team was sold for $250 million to Tom Hicks, an LBO investor and a generous donor to Bush's political campaigns. Bush owned only 1.8% of the team, but his partners awarded him an additional 10% at the time of the sale to reward him for putting together the deal back in 1989. His windfall: $14.9 million, with up to $2 million more expected soon in a second distribution.

Last year, Bush turned about $1.2 million of his newfound riches over to Northern Trust, which now picks stocks for him in a blind trust. But he's also benefited from the investment advice of his business-savvy friends. For example, he's received extensive help from Robert McCleskey, an accountant and former business partner whom he's known since they played baseball together in junior high school.

McCleskey, who currently handles Bush's sizable fixed-income portfolio, says he's been extremely cautious with the governor's fortune: "We don't want to risk the kind of money he made in that Rangers deal." So he's invested more than $6 million of Bush's assets in Treasury bills, explaining: "Our objective is cash flow. Running for governor and President is expensive."

Until Northern Trust took over, McCleskey also helped Bush pick stocks, steering him into a diverse array of sturdy industry leaders like Disney, General Electric, IBM, Intel, PepsiCo and Pfizer. Bush also picked some stocks for himself, including Exxon and a handful of highly speculative oil and gas names such as Parallel Petroleum, a profitless Texas firm with a market value of just $93 million. McCleskey explains: "He'll have a friend who'll start the company, and he'll buy a little stock. Most of them didn't work out. But one or two did."

Rounding things out, Bush also owns a stake in three dry-cleaning stores in North Carolina--another reflection of his habit of doing business with friends. "We still have the dry-cleaning business," says McCleskey. "We haven't made any money, but we'll get our money back."

Now that he's rich, Bush may finally be getting less tightfisted. "He never gave me Christmas gifts before," says Younger, his boyhood friend. "Now I get really nice gifts. A fancy jacket, a good tie. He's changed a bit." Since his Rangers' windfall, Bush has also spread the wealth within his family, setting up new trust funds for his twins, Jenna and Barbara.

But his greatest indulgence is his future home. Bush recently bought 1,583 acres in Crawford, Texas, paying about $1.8 million, says Benjamin Franklin Englebrecht, who sold him the land. The governor is now building a ranch there with a private, man-made lake where he can fish. The house should be finished in November--ideal if he doesn't make it to the White House. Johnson, his Chief of Staff, remarks: "George is hoping to use it as a vacation home."

THANKS, DAD! ALBERT A. GORE

In 1976, Al Gore was elected to Congress at the age of 28. He soon decided not to invest in stocks, since it might create conflicts of interest when he came to vote on legislation. "Now, missing the bull market is not the greatest thing in the world, financially," Gore told MONEY earlier this year. "But for me it was the right decision."

Gore has always liked to portray himself as a straight arrow, dedicated to doing good rather than doing well. Still, he's hardly taken a vow of poverty. As Vice President, he receives a salary of $175,400, plus free housing in a stunning Victorian home. He and his wife Tipper have put in a basketball court next to the pool and have decorated the place with borrowed American Impressionist paintings.

At 52, Gore has managed to become pretty wealthy--without trying. In his latest financial disclosures, he estimates his family's net worth at $1.4 million to $2.5 million. We've discovered that he and Tipper are also likely to receive millions in inheritances--though probably less than Bush will get from his father, who we figure is worth more than $20 million. (Bush Sr.'s Kennebunkport, Maine estate alone is worth about $8 million.)

Gore owes much of his wealth to his father, the late Sen. Albert Gore Sr., who went to great lengths to make his son financially secure and thus free to focus on politics. Gore Sr. always seemed to have a new business scheme--a trait that his son recalled admiringly in a eulogy at the senator's 1998 funeral. "He owned a feed mill. A hardware store and sporting goods store. A towing and auto repair shop. He sold boats and motors. He had a gasoline station.... He ran a commercial egg production house with 10,000 chickens. He built and operated the first so-called pig parlors in this part of the country," said the Vice President.

Gore Sr. helped his son out by including him in several of these ventures. It started as early as 1969, when Al was home on vacation from Harvard. His father arranged for him to receive a low-interest loan from a credit union, which Al used to buy 20 acres of land--from his father. Along with a third partner, father and son then set up a firm, Tanglewood Homebuilders, which built nine houses on the land from 1969 to 1973. Al had little hands-on involvement in the company but made about double his $40,000 investment in those years.

Then, around 1973, Gore Sr. bought some land near his farm in Tennessee and acquired the right to mine it for zinc. He promptly sold the property to his son, who's earned a total of $450,000 over a couple of decades by leasing the property to mining companies. The mine is now estimated to be worth between $100,000 and $250,000. In another 1970s deal, Gore Sr. sold his son some pastureland from his own farm, then leased it back for $4,800 a year.

Richard Boxer, a health policy adviser to Gore, says the Vice President is "not all that interested in business," despite his father's example. In fact, his main source of outside income in recent years was a book--his 1992 bestseller about the environment, Earth in the Balance, which has earned him more than $1.1 million in royalties. Gore donated $50,000 of that money to the University of Tennessee to set up a chair in memory of his sister Nancy, who died of lung cancer.

As a politician, Gore was an early booster of the Internet. But his investments remain decidedly Old Economy. In addition to his mining interests, he has most of his assets in real estate. He owns an 88-acre farm in Carthage, Tenn. that's valued at $445,000. He also owns a nearby rental home, which is worth $66,400. (To Gore's embarrassment, the press reported that his tenants had complained about backed-up toilets and clogged sinks and that the management firm in charge of the property had responded by evicting the tenants. Gore eventually agreed to fix the problems without evicting them.) The Gore family also owns the two-story house in Arlington, Va. where Tipper grew up. Built by her grandfather, the house is now valued at nearly $500,000.

At some point, Tipper and Al also stand to inherit a considerable sum from their parents. As the sole surviving child of Pauline Gore, who is 88, he can expect to inherit more than $1 million in real estate and mining rights. He's also likely to inherit her sizable holding of stock in Occidental Petroleum, which Gore Sr. amassed while running an Occidental coal-mining subsidiary. The Occidental shares were recently valued at between $500,000 and $1 million.

And as MONEY has learned, Tipper will inherit a substantial sum from her 77-year-old father, John Aitcheson. He says he sold his plumbing supplies business in 1999 for $3.9 million and tells us that Tipper will receive part of that money after he dies. He also owns a company called Aitcheson Real Estate Corp., which leases out commercial properties that he says are worth a total of about $2 million. Tipper already owns a stake in the real estate firm, says Aitcheson, and he plans to leave her a bigger share at his death.

Once again, it seems, Al Gore--the man who never cared much about making money--will quietly profit from the trickle-down effect.