Every day before lunch, they all lined up and recited the Angelus. Once Rex whispered something to the boy standing next to him. “Sr. Irmingarda came round with a stick like a banister upright and whacked me on the butt,” he recalls. “It stung, my eyes teared up and I said, ‘Ha ha, your stupid old stick broke.’”

Still, he thrived under the discipline, working hard and raising just enough Cain to amuse his elders. And after six years, he went home. His mom was again stable—a generous uncle had sent money regularly, and she was working as a secretary. Rex enrolled at Bishop DuBourg High School and started cramming: “They grouped you in these tight clusters of people, all really smart and highly motivated,” he says. “Competition does wonders.”

He dated just a bit, secretly sure he was going to become a priest.

But when Rex Sinquefield entered seminary the following year, he already owned $200 worth of Great Northern Paper stock.

“My mother was always fascinated with the stock market,” he explains, “even though she had very little money. So even in seminary, I watched the market.”

Three years later, for reasons he still can’t articulate, he left the seminary. At Saint Louis University, he majored in philosophy and business, where he shone. His professors urged him to apply to the University of Chicago Graduate School of Business.

He did—but was thwarted by the Vietnam War. He wound up a “high-end gopher” in the finance corps at Fort Riley. “The mission of Fort Riley is to prevent Indian attacks,” he says dryly, “and in the time I was there, there was not one attack.” He dealt with top-secret records and found it “easy, boring, safe and a terrible waste of manpower.” He learned judo to pass the time.

•

REX EST QUI METUIT NIHIL.
A king is he who fears nothing.

In the 1950s, everybody knew that the way to make a killing on the market was to pick a handful of winners.

By the late ’60s, neoclassical economists and finance profs at the University of Chicago GSB were saying just the opposite.

Stock prices rose and fell in random patterns, they pointed out; future prices couldn’t be predicted, so there was no point actively managing a stock portfolio. You’d do better to diversify—and trust the market.

Dispassionate ivory-tower theories were lost on the hunch-players and obsessive analysts trading down below. They were the bookies, urging the gamble—and the lure was too strong to resist.

But in 1970, a new MBA student, Rex Sinquefield, showed up at the GSB. He, too, was eager to learn magic stock-picking formulas and make a bundle. Then he took macroeconomics from future Nobelist Merton Miller, who described the intrinsic efficiency of the world’s stock and bond markets.

“It has got to be true,” thought Sinquefield, startled. “This is the only thing that creates order in the universe, in the markets.” Next he took a finance class from Eugene Fama, who again emphasized efficiency: Markets capture new information instantly and incorporate it into their prices, Fama said, so unless you have illegal insider information, there’s no way to “beat” them. Instead, mimic the market with a portfolio so broad, you’re insulated from individual stocks’ volatility.

Sinquefield listened to Fama’s coolly logical lectures and felt his old assumptions spin about 180 degrees—then click into place. He finished his MBA, took a job at American National Bank of Chicago and put his professors’ ideas into practice, developing, in 1973, the very first S&P 500 passively managed index fund. “Index” because its portfolio was selected to perfectly mimic, not beat, the larger market. “Passive” because he didn’t handpick and continually buy and sell; he chose for certain variables and then held steady.

There’s a bit of contradictory lore about Sinquefield’s “first”: Some say John McQuown at Wells Fargo beat him to it. “There’s no doubt who started the first market-weighted index fund in the galaxy,” Sinquefield says firmly. “That was me.” McQuown’s 1971 attempt, for a Samsonite pension fund, was unwieldy; his fix came after Sinquefield’s coup.

“I think it’s a tie,” chuckles Fama.

Next, Sinquefield partnered with Roger Ibbotson, one of his U. Chicago teaching assistants. Starting with a database at their alma mater that listed stock results from 1926 to 1964, they rolled up their sleeves and began to gather fresh numbers, bringing the original database up to 1975 and adding risk and return data for government bonds, Treasury bills and inflation. This made it possible, for the first time, to compare various markets’ performance over time—and do long-range forecasts. “We said the stock market would outperform the bond market and hit 10,000 by 2000,” Ibbotson recalls, “and it did.” (“It’s not above that now,” he adds wryly, “but it did.”)

Published in 1976, Sinquefield and Ibbotson’s Stocks, Bonds, Bills and Inflation showed that, over time, stocks had outperformed less risky government securities. The book was the second most frequently cited source in investment research for the next 15 years. And it changed the way much of America—especially large institutions—invested its money. Today, Sinquefield says, about 40 percent of all institutional assets are in index funds.

•

ERGO SUM REX GLORIAE.
I am a king of renown.

Sinquefield also stayed in touch with another U. Chicago TA, David Booth, who was forging his own path into index funds. Their academic bent made the financial establishment nervous, so in 1981, they co-founded their own company, Dimensional Fund Advisors in Santa Monica, Calif., and started the first passive fund focused on small (microcap) companies customarily ignored in large institutional portfolios. Future Nobelists piled onto DFA’s board, eager to see their theories finally executed.

DFA’s computer models are sophisticated, its clients mainly institutions—state pension funds and the like, with portfolios big enough to be truly diversified ($2 million per fund minimum, in at least six to 10 funds). Individuals can enter DFA funds through carefully vetted investment advisors, the largest being Buckingham Asset Management and its Advisor Services, here in St. Louis. “You go through a process to be approved, because they want to make sure you will adhere to the buy-and-hold strategy,” principal Ed Goldberg tells me. DFA doesn’t want any erratic selling and buying, because “hot money moving in and out of the market” can introduce “noise,” evaporate liquidity and throw off estimated returns.

Three factors matter a lot to DFA: market (over time, stocks have outperformed fixed-income investments); size (over time, small-company stocks, which are riskier and therefore cheaper, have outperformed large-company stocks); and price (over time, lower-priced “value” stocks have outperformed higher-priced “growth” stocks).

The key phrase is “over time”; even today’s losses, which DFA funds are suffering right along with everybody else, can eventually be recouped. This is a strategy for patient, disciplined investors, not impulsive or greedy ones. “DFA did pretty well in the early 2000s, after the tech bubble burst,” notes Ohad Kadan, associate professor of finance at Washington University. “The strategy is not working well recently—but it’s dangerous to make inferences from one year.”

Especially this year—when free-market fundamentalism has been blamed for global economic woes—Booth, who remained as DFA’s CEO when Sinquefield retired in 2005, wishes his partner were still around to distill the current craziness for their clients: “He’s great at formulating problems, and taking his Jesuit training and being persuasive with it.”

“He’s very good at telling a story to institutional investors,” agrees Fama, who joined DFA as director of research but still holds a distinguished professorship at the Graduate School of—

“Wrong,” he interrupts. “It’s not the GSB anymore.”

“But your email goes to chicagogsb,” I protest inanely.

“It got a new name last Friday,” he says. “As of November 6, 2008, it is the Booth School of Business. There was a $300 million gift.”

Sinquefield’s given to the University of Chicago, too—even endowed a chair in Fama’s name. But when David Booth’s gift, the largest in any business school’s history, was announced, his longtime partner was here in Missouri, using his profits to push free-market public policy.

“Now he’s going to cure Missouri’s problems,” chuckles Fama. “Shows you how naive he is—he thinks they are going to drop the state taxes!” He sobers. “It always looked like Milton Friedman was tilting at windmills, too. But his ideas caught on.”

•

SUUS REX REGINAE PLACET.
Her own king is pleasing to the queen.

Jeanne Sinquefield answers the door, apologizing breezily for her sloppy brown pullover and corduroys (she cares what you think but not how she looks). The hallway’s abuzz with party planners: The Sinquefields are hosting a reception with the Today and Tomorrow Educational Foundation, to which they’ve donated $500,000 to give city kids scholarships to private religious schools.

Jeanne lets me peek into Rex’s study: shredders, economic treatises, chessboards and one of what he calls his “brain-rot” paperbacks (Lee Child, John Grisham, John Sandford). With a wifely shrug at the mess, she starts talking intently about her research into the demographics of student academic performance and how lots of poor black kids don’t even live inside city boundaries. Like her husband, she loves to toss contrarian facts at prevailing assumptions.

They met at the University of Chicago, both breathing its thin, cerebral air in great gulps. Specifically, they met at Judo Club—and she threw him. Smart, outgoing and plainspoken, Jeanne already had her MBA and was finishing a Ph.D. in demography. Rex always managed to sit near her at the Eagle, where everybody went after judo to drink beer and eat burgers and solve the world’s problems. One day, he stood near her carrel in the library, waiting for her to get up so he could bump into her by accident and ask her out.

They saw each other every day after that. Rex moved into Jeanne’s apartment, and in nine months—with Jeanne away for five of them, doing demography in southeast Asia—they married. “In Indonesia, they talk about people being chocho,” she says. “The literal translation is ‘the key fits the lock.’”

They’ve raised three children and worked together every day since. As executive vice-president of DFA, Jeanne ran the all-important trading department. She shares her husband’s political agenda (free the markets, improve the schools, eliminate taxes and government intervention) and adds her own pet causes, from the Boy Scouts to the use of neurofeedback therapies to treat autism.

She sits with us during the first interview—which feels a bit like an audience. Rex is flanked by his wife, an assistant and Laura Slay, his PR person, and they all listen with interest to his answers and laugh at the right places, and it’d feel a little silly if he didn’t crack the stereotype by rising midcomment to fetch coffee for his wife and anyone else who wants some.

Fortunately, he’s not someone who lets himself be handled, scripted or silenced. Nor does he bother with niceties, small talk or flattery. At one point, after he breaks off an answer about their easy and companionable marriage, Jeanne’s eyes fly open. “Almost got a compliment out of him!” she murmurs.

The biggest myth about the economic downturn, Rex informs me, is “that it was caused by deregulation. That’s an out-and-out lie. Without government inducements and government pressure, these banks would not have made these subprime loans. Fannie Mae basically dropped the credit-quality requirements, and you had about a trillion dollars of this stuff infecting the world. It was 100 percent avoidable.”

I hand him a Jacob Weisberg quote from Slate.com guaranteed to infuriate him: “A source of mild entertainment amid the financial carnage has been watching libertarians scurrying to explain how the global financial crisis is the result of too much government intervention rather than too little … their heroic view of capitalism makes it difficult for them to accept that markets can be irrational, misunderstand risk, and misallocate resources …” By the time I reach the end, Sinquefield’s smiling almost fondly. “There’s a lot of emotionalism in that” is his only comment. “If you read it carefully, you see him start ranting and raving.

“It’s hard to stay cool right now,” he continues. “This is a time of great stress. If the typical working person isn’t a little bit scared, they’re not normal.”

So what should they do?

“Stay cool.”

If he’d been U.S. Treasury Secretary Henry Paulson last fall, what would he have been doing? “Getting a hair transplant.”

What advice would he give President Barack Obama? “Resign.” He laughs to soften the answer (“How many people am I pissing off?”). Then he turns as grave as a disappointed headmaster. “I don’t think I’d waste time giving him advice. He’s got to figure out who he is and what he really stands for. I don’t think he knows yet.”

OK, what about the increasing gap between the wealthiest and the poorest—what should we do to close it? “Nothing. It’s always going to happen; it’s just a matter of statistics: As the sample size grows, the extremes will get farther apart. While the poor are getting richer, someone is going to get extremely rich; the upper end is not bounded.”

As Sinquefield’s fond of saying, “Facts are facts”—and in his mind, it’s a fact that the market is supremely efficient, and its forces can only improve education and other public enterprises. Taxes are disincentives, so anything taxed will decrease: income, spending, business. Government’s job is to protect our rights and get out of the way. Ours is to be disciplined and patient, work hard, trust the market … and hold back the tears.

When he leaves a second time—the coffee now ready—Jeanne blurts, “I can’t believe he didn’t mention the surgeries. He had all these operations, 18 of them, for cleft palate before he was 5. They must’ve been expensive; I bet that’s one reason his mother couldn’t keep him at home.”

There’s no time to ask—already another gaggle of folks has arrived, and they are milling about in the hall. The Sinquefields’ personal lobbyists use every available time slot to schedule meetings with politicians and community leaders who might advance their clients’ public-policy agenda.

Weeks later, at a second interview, I murmur, “Jeanne was surprised that you didn’t mention the surgeries. Were they rough?”

“Nope. The doctors did all the work.”

Sinquefield’s friends recall how in Chicago, when his apartment porch cracked under the weight of falling ice, and he broke “one leg and one back,” he joked his way through months of metal-pinned traction. Asked about his decision to leave the seminary, he quips that he couldn’t start as a bishop. He likes to say he married Jeanne on New Year’s Eve so they’d get the tax deduction for the entire year (which, he adds, saved them $350).

The king has a bit of court jester in him. But underneath, he’s very, very serious.

•

REX EST QUIQUE CUPIT NIHIL.
A king is also he who desires nothing.

In 1997, the Sinquefields bought themselves a farm in the Ozarks and started building. They were already planning their return.

In 1999, Rex flew in to see the pope and ran into Ron Holtman, his old coach at St. V.’s.

“I said, ‘What do you do these days?’” Holtman recalls. “I knew he was helping out St. Vincent’s; I thought he probably gave a couple hundred bucks a year. He said, ‘I’ll send you some information.’ This big brown packet full of Forbes and other magazines and books shows up, and he’s on the cover of lots of them as this economic guru!”

Sinquefield’s life had come full circle; he’d proven himself to the man who’d been his father figure in those stoic years at St. V.’s. “He taught me respect, competition, self-discipline, teamwork, just how to behave,” Sinquefield recalls. “He was such a perfect person. I tried to be as clever as he was—problem was, he remained clever, and I ended up being a wiseass.”

When I repeat this to Holtman, he chuckles. “At times, yeah! As the German nuns would call him, a wisenheimer. I remember him as a very young fellow with lots of energy, always a big smile on his face and a quick wit. He and one other guy were the smallest on the team, but he had this analytical mind, always knew where the ball was going to be.”

In 2005, the Sinquefields retired from DFA and moved back to Missouri permanently, dividing their time between the farm—now a lush 1,000-acre spread used to host a slew of charitable events—and a mansion in the Central West End. One of the first things Rex did was bring people to what was now called St. Vincent Home for Children and show them “every nook and cranny,” development director Jo Curran says, “telling little-kid stories about his time here.” Were they potential donors? “Oh no. These were people near and dear to him. He doesn’t bring donors here; this is a very personal thing for him. This was his home.”

Next, eager to build an art collection, he hired a “director of art and culture”—although he does know what draws him. “I’m struck by colors, emotions,” he says, surprising me. “It has to have sort of a romantic, lyrical feel about it.” He pauses. “When I fall asleep at night, I listen to a CD, and it’s always the second movement, the adagio.”

Sinquefield shows a son’s loyalty to the church; he advises the archdiocese on finance and says he believes “everything the Catholic Church teaches.” He’s somebody you can’t imagine having an affair or getting into any sort of muddle; he thinks in orderly compartments and lives the same way. Long walks, spinach, lean meat … His single indulgence is fine wine; his passion is chess.

Last year, he gave money to build one of the world’s finest chess centers in the Central West End; this spring it will host both the U.S. Chess Championship and the U.S. Women’s Chess Championship. He’s about to enter tournament chess himself; he’s been studying with Jennifer Shahade, two-time American Women’s Champion and author of Chess Bitch. “He’s an aggressive player,” she reports. “Whenever he gets a chance, he’ll try to attack his opponent’s king.”

Sinquefield relishes the lessons. “She says I’m aggressive,” he confides. “I didn’t know that. It’s like being an entrepreneur; entrepreneurs are inherently cautious. On the chessboard, sometimes the best move is the most conservative move. However, it can lead to very sharp-edged positions.”

•

REX REGNANT SED NON GUBERNAT.
The king reigns but does not govern.

For an arriviste, Sinquefield cuts quite a figure in St. Louis. He’s on nearly all of the big boards, from the Opera Theatre of Saint Louis, Saint Louis Art Museum and Saint Louis Symphony to the Missouri Botanical Garden and Saint Louis University. His parties are rich with food and drink and sparkle with interesting artists—who tend to talk among themselves, because what really engages his interest is a nice, wonkish policy debate.

When Sinquefield moved back to Missouri, he promptly co-founded the Show-Me Institute with Kansas City’s R. Crosby Kemper III, a wealthy banker who’s now executive director of the Kansas City Public Library. A think tank with offices in Clayton, Show-Me commissions studies on public-policy issues. Its motto is “Advancing liberty with responsibility by promoting market solutions for Missouri public policy.” That’s liberty (no regulation), responsibility (personal), market (free).

Sinquefield’s priorities are to repeal Missouri’s income tax by 2012 and wipe out St. Louis’ and Kansas City’s earnings taxes, perhaps replacing them with land taxes. Even more urgently, he wants public schools to be forced to compete against charter and private schools—and, if they can’t make the grade, to close. “Only in the education business,” he remarks, “is there no penalty for failure.”

Other positions flow from Sinquefield’s beliefs that markets are efficient and should not be regulated; that individuals should be responsible for their own safety and survival; and that competition ensures quality. Show-Me opposes corporate welfare—whether it takes the form of tax breaks or subsidies or cavalier uses of eminent domain—and fought hard against the recent increase in Missouri’s minimum wage. (It was approved with 76 percent of the vote.)

One Show-Me study defends the payday-loan industry as “highly competitive,” its high interest rates a rational response to risk. One says price gouging after natural disasters is beneficial, because sky-high prices encourage businesses to sell more of what’s needed. Another says regulations protecting residents in assisted-care facilities increase costs so sharply, the care becomes unaffordable. And Show-Me author Randal O’Toole, a senior fellow at the Cato Institute, pronounces light rail “a hoax perpetrated on taxpayers,” claiming buses are cheaper, faster and safer.

Obviously, the institute attracts like-minded scholars—Show-Me’s authors are vetted, often meeting with Sinquefield so he can decide if their heads are screwed on straight. But are the purchased study results biased in advance? They certainly weren’t in a recent study of the Missouri Plan, the state’s method of judge selection. Conservatives are eager to change Missouri’s system, but the study found it to have no economic disadvantages, compared to other nonelectoral systems. Sinquefield reportedly wasn’t thrilled by this conclusion; indeed, Show-Me promptly released a statement pointing out that there could be less tangible downfalls to the Missouri Plan. But Joseph Haslag, Kenneth Lay Chair in Economics at the University of Missouri–Columbia and an executive vice-president of Show-Me, says Sinquefield simply asked whether the methodology was sound. Assured that it was, he published the results.

•

IN REGIONE CAECORUM, REX EST LUSCUS.
In the realm of the blind, the king has one eye.

Sinquefield’s free-market ideas aren’t exactly in ascendancy. Even the University of Chicago is thawing its frozen neoclassical mold, with new academic stars like Richard Thaler blaming the current economic mess on “human frailty” and pointing out moments of wild irrationality in markets’ behavior. Not only are there unpredictable bubbles and pops, there are also human variables, illogical decisions, messy outcomes.

Even if markets did stay cold and pure, you’d have paradox: Market efficiency comes from everybody looking for the best deal; it’s all that information pouring in that determines price. But if everybody’s sure markets are efficient, no one will do any research—and then markets won’t be efficient.

“I don’t think we have to worry about that,” drawls John S. Howe, Missouri Bankers chair and professor of finance at the University of Missouri–Columbia. “Too many people think they can be Warren Buffett.”

Sinquefield once quipped that Buffett, the self-made billionaire investor famous for his snap decisions, could be matched by an unusual orangutan. What he meant was “Warren Buffett’s an outlier. Every several generations, you are going to find somebody like that. If you read what he recommends for everybody else, he says over and over that investors should buy index funds.” There’s no single person, Sinquefield maintains, who can systematically have more information than a dispersed market of 6 billion people.

His own portfolio’s spread wide—“I probably own 20,000 securities”—and he doesn’t worry about socially responsible investing; his activism takes the form of political contributions to just about anybody who shares his thinking.

Between January 1, 2007, and December 1, 2008, Sinquefield gave more than $2.9 million to various Missouri candidates and coalitions, according to the Missouri Ethics Commission’s records. To keep the contributions legal, he carefully channeled the money through 100 different PACs, dissolving most of them over Thanksgiving weekend after the Missouri legislature removed contribution limits. (That bill was passed by Missouri’s House of Representatives 83-72. And of the 42 reps who’d received donations from Sinquefield, 36 voted yes, notes the Missouri Citizen Education Fund.)

Sinquefield spent $800,000 to help Missouri quash a lawsuit filed by 262 school districts asking for more funds. Gave more than $100,000 to the attorney-general campaign of Chris Koster and another $45,000 after he won the election. Gave $100,000 to gubernatorial candidate Kenny Hulshof  after he spoke for taxpayer subsidies for private-school tuition. Gave $100,000 to Mayor Francis Slay for being “an ardent supporter of charter schools.”

Political types talk knowingly about “Rex,” no surname needed. To gauge access, the tell is “Have you been to the farm?” But friends praise Sinquefield’s character as well as his generosity—and when I ask for his shortcomings, they go blank. After a long pause, longtime DFA partner Booth says, “He doesn’t dance very well.” Lt. Gov. Peter Kinder says Sinquefield’s only weakness “is probably an excess of generosity.” Fama demurs: “He endowed a chair in my name here, so I can’t have much to say!” Haslag fumbles, then blurts, “I think he’s got the goofiest hats I’ve ever seen.”

A few academic types, insisting on anonymity, dismiss Sinquefield’s blazing success with a shrug: “Right time, right place.” But none deny that he’s made an immense contribution. “He’s not brilliant as a theorist,” one says, “but he’s almost visionary.”

Yet he’s been “demonized,” his supporters say, baffled by the snarling hostility. Why attack the king? Because he’s endangering the free public education and government services they think should be part of a democratic society. Rep. Jeanette Mott Oxford (D-St. Louis) calls Sinquefield’s support for school choice a dangerous distraction from real social problems and a diversion of much-needed funds from the public schools. Chris Guinther, president of the Missouri chapter of the National Education Association, says she can’t help thinking how many new teachers the public schools could hire if they had the kind of money Sinquefield’s using to promote charter schools instead. “Competition is fine in the business world,” she says, “when you are working with the same raw material. We’re dealing with children with a lot of different needs and abilities. And only public schools accept them all.”

Sinquefield sees criticism as inevitable broken eggs. But … where’s the omelette?

“My gut feeling is that he is not having as much influence as the amount of money he is throwing around would suggest,” says Peter Downs, president of the St. Louis School Board. “He says competition is the solution to everything—and you can have competition without spending money—and that ideological framework has taken a big hit just since the failures of Wall Street.”

Show-Me has racked up a few legislative successes, influencing a cable franchise reform bill and HB 818 (which made Missouri the first state to allow employers to contribute pretax dollars to employees’ health-savings accounts). Show-Me’s also kicked up a healthy fuss about eminent domain and provoked new debate about taxation. But Haslag surprises me by saying he thinks the Chess Club “may in some ways have a longer run and even a more immediate impact. It’s a way to improve cognitive skills, it’s very concrete and there are spillover benefits for every kid who’s willing to put the effort into it.” That includes kids from St. Louis Public Schools, where Sinquefield funds chess programs.

Public Eye founder Richard Callow, a master strategist who keeps his finger on the pulse of anyone with power, says, “I think Mr. Sinquefield is a glacier. You’ll mistake him for a mountain, until you realize that he is inexorably moving through the valley reshaping the landscape.

“Passionate people always have more influence than bloodless ones,” Callow adds, then moves to the more obvious metaphor: “In chess terms, Mr. Sinquefield is playing to control the d5 square. He has only made a few moves, but it would be a serious mistake not to notice how strong his game is.”