Joe Ricketts: The new billionaire political activist

After amassing great wealth building TD Ameritrade, Joe Ricketts bought the Chicago Cubs for his family. Now he is spending millions to promote his political vision and unseat the president. Meet a big behind-the-scenes player in the newly deregulated electoral system.

FORTUNE — I am perched atop a hay bale in the glorious Wyoming mountains, the majestic Teton Range crowning a landscape of unspoiled beauty. Surrounding me is a 240-strong herd of grass-fed bison. A couple of them eye me warily as they munch on my temporary seat. I feel a bit like an intruder, but I’m the invited guest of J. Joe Ricketts, the billionaire founder of what is now TD Ameritrade (AMTD) and the owner of this 1,300-acre swath of land. While here I learn how to fly-fish in Lake Marlene — named for Ricketts’s wife of 49 years — behind his sprawling western-style home. I sample bison pastrami. I ride in a wagon drawn by his Percheron draft horses, which have won awards at the Calgary Stampede.

There’s only one thing missing: Joe Ricketts. He prefers to remain behind the scenes. But his money is having an outsize influence on the 2012 election.

Since Ricketts, 71, stepped down from TD Ameritrade’s board in 2011, he has become increasingly prominent on both the business and the political scenes, with an eclectic collection of entrepreneurial ventures and an eight-figure commitment to defeat President Obama. Yet that hasn’t translated into a desire to explain himself to a journalist. The tall, doughy Nebraskan doesn’t want to talk about his first feature film — directed by Robert Redford — or his own media enterprise, local news site, or his bison ranch, or his charity that helps educate children from underdeveloped countries (though he did provide us with pictures). He doesn’t want to talk about Ameritrade, the electronic brokerage he founded in 1975, or his purchase of the Chicago Cubs on behalf of his four children. He especially doesn’t want to discuss the controversy over a proposed anti-Obama ad campaign that landed him on the front page of theNew York Times, with repercussions for both his causes and his family — or the new, $10 million campaign featuring disappointed former Obama voters that is about to flood the airwaves.

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No, Ricketts wants to do things his way — which mostly means maintaining control. So while he refused to be interviewed, he invited others to extol him, including executives from Hugo Enterprises, his holding company; Ending Spending Action Fund, the Super PAC that carries out his political objectives; and his son, Tom Ricketts, the Cubs’ chairman. They all say Joe Ricketts is a man who changed an industry forever, a patriot who wants to return to the good old days of national fiscal responsibility, and a patriarch who is building a new American family dynasty. “He is a great visionary with a true entrepreneurial spirit,” says Kurt Halvorson, Ameritrade’s former chief administrative officer. “He dreams big and thinks big.”

The portrait that emerges from dozens of conversations and journeys to Washington, Chicago, and Wyoming is more nuanced: It is one of a maverick full of contradictions. Ricketts is a self-made man who preaches fiscal austerity while his family’s baseball team offloads business costs on the public; a media executive who won’t give an interview; a man indifferent to baseball who bought one of the sport’s best-known teams; a donor to the poor in the developing world who wants to cut spending on poverty at home; a supporter of politicians who oppose gay rights whose daughter, Laura, has helped create a Super PAC called LPAC, for Lesbian Political Action Committee.

Yet Ricketts, whose family is worth an estimated $1.9 billion, is not just another rich dude. He is one of the small group of billionaires taking advantage of the changes in campaign-finance law to influence the nation’s political discourse. You may not be familiar with him — he’s no Sheldon Adelson or George Soros— but he’s one of the big players on the American political scene, and you’ll be hearing from him plenty in coming weeks.

For Ricketts, the most important issue is cutting federal spending and taxes to tackle the debt crisis. It’s a straightforward position. But as Ricketts has discovered the hard way, writing a big check is one thing; controlling what your money accomplishes is quite another. It turns out that in politics, as in business, deregulation is a powerful and unpredictable thing.

Joe Ricketts actually possesses the asset that so many politicians love to claim: an up-by-the-bootstraps biography. Born in Nebraska City, Neb., to a carpenter and a homemaker, he grew up poor, with three brothers and a sister. His first job was in third grade, working as a janitor’s assistant.

After working his way through Creighton University, a Jesuit school in Omaha, Ricketts became first a credit analyst at Dun & Bradstreet (DNB), then a stockbroker. In 1975, when the SEC deregulated broker commissions, the 33-year-old Ricketts saw an opportunity. Why should investors have to rely on full-service brokers when many of them knew what they wanted to invest in anyhow? The same year, with a few partners, he opened First Omaha Securities. “No one had really brought Wall Street to Main Street,” says J. Randy MacDonald, Ameritrade’s CFO from 2000 to 2006. “The pioneers of discount brokerage were three people: Charles Schwab, Joe Ricketts, and probably Muriel Siebert.”

Ricketts’s best insight was technological. His firm was the first to execute trades using the touch-tone phone instead of a live person, in 1988. In 1995 he saw the potential of the Internet and scooped up K. Aufhauser & Co., one of the first firms to use the web for trading.

He also worked his tail off to make his company a success. The four Ricketts children — J. Peter, now 48; Tom, 47; Laura, 45; and Todd, 43 — helped out too. “We didn’t take vacations,” remembers Tom. “We stuffed envelopes on weekends, and we got paid in sugar cubes.” Dad took the kids to baseball games and occasionally coached their teams, but he had little interest in the box score. “He’d bring a cigar and sit up in the top row by himself and think about the day,” Tom says. Ricketts’s ambition stretched far beyond the outfield. He announced he would become the largest discount broker, as measured by trades per day.

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Ameritrade, as the company was known by 1996, didn’t feel like a dotcom, but it soon became one. The company, along with Schwab (SCHW), E*Trade (ETFC), and Datek, was a player in the fast-growing online-brokerage market and went public in 1997. By 1999, thanks to the Nasdaq bubble and Ameritrade’s ad campaign featuring Stuart, the red-haired slacker with the $8 trade, Ricketts, who had retained 55% of the company, was worth more than $2 billion. The man who rarely bought a new car came up in the same sentences as the Oracle of Omaha himself,Warren Buffett.

Buffett stayed in his modest home, but Ricketts began to enjoy the fruits of his labor. In 1998 he bought the spectacular ranch in Little Jackson Hole, Wyo., on which he would later raise bison, and the next year he spent $7 million to buy the most expensive house ever sold in Omaha, a 17,000-square-foot mansion formerly owned by James Crowe, CEO of Level 3 Communications (LVLT). Later he would purchase a 78th-floor penthouse in New York City’s Time Warner Center for $29 million, a sleek, modern space that he decorated in a western motif. Yet he was no socialite, preferring a ride to the Sturgis Motorcycle Rally on his Harley-Davidson Springer Softail Custom to chairing a ballet gala.

He did make at least one memorable public appearance. At the Omaha Press Club’s annual dinner in 2000, the three local billionaires — Warren Buffett, Level 3’s Walter Scott Jr., and Ricketts — sat on stage. Suddenly Regis Philbin’s face filled a videoscreen. “Let’s play Who Wants to Be a Jillionaire?” he sang out. When the three discovered that the grand prize was only $1 million, they stalked off the stage. “We’re outta here,” said Ricketts to hoots and applause before coming back to answer questions. When asked if he was nervous, he said, “Not a bit. It’s the first billion that’s really hard on you.”

Even though Ricketts was rich beyond his wildest dreams, he was still wide-eyed when it came to big-spenders’ protocol, thrilled to be able to use his American Express Black card to pay for dinner one night in 2000. As a joke, when he went to use the bathroom, MacDonald told the waiter to pretend Ricketts’s card had been rejected. “He looked like he was going to cry,” MacDonald remembers, before letting Ricketts in on the ruse. “I wasn’t sure if this was going to be ‘Ha-ha-ha’ or ‘You’re fired,'” he says. Ricketts was a good sport.

Then came the dotcom crash. Ameritrade’s stock fell an astonishing 94% between 1999 and 2001, along with Ricketts’s net worth. And although he had been grooming his son Peter as his successor, it became clear that Ameritrade needed outside help. In came Joe Moglia as CEO, a rah-rah Merrill Lynch executive with buckets of street cred and a strategy of rolling up all the existing players.

Ricketts had a hard time watching his ownership stake diluted as the company bought National Discount Brokers, in 2001, followed by other brokerages, including Datek, and ultimately, in 2006, merged with TD Waterhouse. “We could already see the anxiety in his face,” says MacDonald of the first big deal. “It was pretty clear to all of us that that was always the big issue with Joe — control.” Ricketts’s percentage of the company shrank to 15.2%, but the value of his stock grew.

Although Ricketts was no longer CEO, he still held out hope of regaining control of the company. That’s one reason he supported a deal with E*Trade rather than TD Waterhouse, a debate that split the board between the Ricketts contingent, which included Ricketts and his sons Pete and Tom, and the private equity group that had come into the company with Datek, including Stephen Pagliuca of Bain Capital and Glenn Hutchins of Silver Lake. But E*Trade was seen as a much riskier play because of its large real estate loan portfolio. “We potentially would almost be out of business if we did the E*Trade deal,” Moglia says. In the end, TD Waterhouse improved its offer, and the Rickettses came onboard. Today TD Ameritrade is thriving, with total client assets of $445 billion. Says MacDonald: “Joe feels that Moglia and I sort of undermined him. He’s right. And he cried all the way to the bank.”

Completely uninterested in standard retired-guy leisure pursuits like golf (says son Tom: “He doesn’t have hobbies; he has passions”), Ricketts moved into the next phase of his life. In 2004, with two of his sons and a group of friends, the 63-year-old Ricketts climbed to the summit of Mount Kilimanjaro. There he fell into conversation with his guide, a Masai man named Shange Wilson, and learned that Wilson was using his meager savings to build a school in his village. Ricketts returned the next year and announced that he was starting the Educational Opportunity Foundation. Since then, the foundation has given more than $10 million of Ricketts’s money to more than 1,200 schools in Africa, Asia, and India. Says Tom Ricketts: “Dad gives rich guys a good name.”

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Ricketts wasn’t done being rich either, proclaiming that he would soon make another billion — not by, for instance, investing in other people’s hedge funds, but by building new businesses. He began with, of all things, bison — which is how I ended up in Wyoming. Like fellow mogul Ted Turner, Ricketts saw big bucks in bison as an alternative to red meat, and in 2004 started High Plains Bison. Today it is one of the top five players in the $279 million bison-processing business, though that’s a long way from $1 billion. Compared with the 45 Ted’s Montana Grill locations, there is just one restaurant — Bison Jack’s in Milwaukee — where, says an employee, “we’re doing pretty good at lunch.” Bison is, however, the “Official Lean Meat of the Chicago Cubs.”

Another new venture for Ricketts is a hyperlocal media website called Launched in New York City in 2009, the site, staffed by a hungry pack of young journalists armed with videocameras, has already made a mark. Reporters cover one neighborhood — say, the Upper East Side — and produce stories about anything from local crime to zoning problems to a pizza-eating goat at the Famous Famiglia restaurant in Times Square (that one went viral). The site, while not yet profitable, boasts 1.5 million visitors per month, notable for any media company.

Another media venture has not been quite as successful. In 2008, Ricketts created the American Film Co. to produce historically accurate films about the U.S. Despite having no movie experience, Ricketts persuaded Robert Redford to direct its first film, The Conspirator, which tells the story of how the mother of one of the conspirators to assassinate Lincoln was put to death despite scant evidence that she knew of the plot. Ricketts took great pride in the film’s detail, employing historians to ensure accuracy down to the buttons on the military uniforms. But the movie grossed just $11.5 million in theaters despite its big-name director and $25 million budget. Alfred Levitt, Hugo’s president and general counsel, says new films are in the works, including one about Teddy Roosevelt

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