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 DNAinfo.com, 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 the New 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.
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.
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.”
MORE: Stop beating up the rich
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 DNAinfo.com. 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.
Yet the business Ricketts is best known for these days is no ground-up venture, but rather the Chicago Cubs, one of the most storied — and star-crossed — teams in baseball. In 2009 a trust that he and Marlene funded bought 95% of the team for $845 million, with ownership going to their children. He must really love his kids — all huge Cubs fans since they moved to Chicago for college — because he doesn’t even like the sport. Tom Ricketts says it’s tough to get Joe to attend a game. “He said it was like buying a Picasso,” says Jerry Reinsdorf, who owns the Chicago White Sox and the Chicago Bulls. “It doesn’t matter what it costs; it will never go down in value.” That assumed that the family would be able to renovate Wrigley Field, the creaky relic from the days before luxury boxes determined profitability. The assumption would soon be put to the test.
Even before Joe Ricketts was a billionaire, he had a deep interest in politics. Once a Democrat, then a Republican, now an independent, he had been politically active in Omaha’s Republican Party in the 1970s, more interested in policy than in personality. He grew increasingly interested in fiscal issues, such as taxation and government spending, becoming a strong advocate of cutting both and serving on the board of the conservative American Enterprise Institute.
Joe Ricketts preferred to effect change behind the scenes, but in 2005 his eldest son, Pete, announced he was leaving his job as Ameritrade’s chief operating officer to run as a Republican against Ben Nelson for the U.S. Senate representing Nebraska. Pete, then 41, had youth and wealth — he spent more than $12 million of his own money on the campaign, more than eight times what his opponent spent. A social and fiscal conservative, he lost by an incredible 28 percentage points. It didn’t help when it came out that, two months before he ran a commercial playing up his regular-guy bona fides, his dad had closed on that $29 million penthouse in New York.
But Rickettses don’t give up that easily. Pete went on to become, in 2007, the Nebraska Republican Party’s national committeeman. And his dad decided he had enough time and money to dive deeply into politics — on his own terms. In 2010, Joe Ricketts formed an advocacy group called Taxpayers Against Earmarks, hiring a lawyer named Brian Baker to run it. Earmarks — allocations for local projects tacked onto a bill in exchange for a vote — symbolized the me-first mentality that Ricketts felt was ruining the country. The group spent $1.3 million on advertising, categorizing Democratic and Republican congressmen alike as either “heroes” or “hooligans” depending on how frequently they used earmarks. Ricketts himself met with congressmen in Washington. The public attention and resulting embarrassment helped the passage of a two-year moratorium on earmarks in 2010. For a political neophyte, it was a stunning victory.
Emboldened, Ricketts established a Super PAC in 2010 called the Ending Spending Action Fund. He changed the name of his nonprofit 501(c)4 group from Taxpayers Against Earmarks to Ending Spending Inc. and gave it a new, more ambitious mandate: “To make sense of the federal budget, to end wasteful government spending, and to expose elected officials who say one thing and do another.” The message was simple: Support anyone who has voted for “an enforceable cap” on federal government spending (“spending sheriffs”); get rid of anyone who hasn’t (“budget bandits”).
Ricketts’s new push into politics coincided perfectly with a dramatic shift in campaign-finance regulation. Already the trend had been toward more private money in politics. Then came two major court decisions, which together overturned at least 60 years of campaign-finance law. First, the Supreme Court’s Citizens United decision allowed a corporation — or any group — to make independent political expenditures. Two months later, in a case called Speech Now, the D.C. Circuit Court of Appeals ruled that if the Supreme Court was no longer fearful of potential corruption from groups, it would be a violation of a group’s First Amendment rights to limit the amount it could contribute.
Now political action committees — renamed Super PACs — could collect unlimited amounts from any person, group, or company, as long as they did not contribute directly to the candidates or let them see or approve their plans. Donors could also give unlimited funds anonymously to a Super PAC’s accompanying 501(c)4 nonprofit, which must be primarily a “social welfare” organization.
Although Ricketts is making most of his donations to his own group rather than combining forces with others, the change means that people like him — or Adelson or Jeffrey Katzenberg — are now in a position arguably more powerful, and less regulated, than the political parties themselves (although many Super PACs are controlled by top former operatives of political parties). As of Sept. 18 — still seven weeks before the election — Super PACs had spent some $244 million, according to OpenSecrets.org, compared with $52 million by the parties, with much more to come. “One good analogy,” says Paul Ryan — not the vice-presidential candidate, but a senior counsel at the Campaign Legal Center, a nonpartisan Washington group that studies political financing — “is that wealthy interest groups get to sit in the front row with bullhorns.”
It was in this environment that Ricketts stepped up his activism, supporting anti-incumbents who pledged to tackle the deficit by any means necessary. “It’s about ‘How do we change the policy?'” says Baker. “You have to put new people in, and we have to get rid of the people that are bad.” Ricketts donated $6 million to his nonprofit as well as other groups including AEI, Americans for Tax Reform, and the Campaign for Primary Accountability. Then he turned his attention to a few strategically important congressional races, spending almost $1 million to support candidates with advertisements (see chart above). While Ricketts says he cares only about fiscal issues, all the candidates his Super PAC supports are also social conservatives opposed to abortion and gay marriage.
Which brings us to yet another interesting contradiction in the Ricketts family: His own daughter, Laura, is an out lesbian and political activist against those very issues. A former lawyer who is now, with brothers Tom and Todd, running the Cubs, she serves on the Democratic Party’s LGBT leadership council and sponsors events such as Out at Wrigley Field for All Families. She is also a major fundraiser and bundler for President Obama.
Ricketts is certainly not the first dad to disagree about politics with his offspring. “We love each other,” says Tom of his family. “Political positions don’t define us.” Yet father and daughter seem to be running their own private arms race. In July, Laura Ricketts announced the formation of LPAC, a Super PAC aimed at lesbians. As she told a Chicago podcast, The BEZ, in July: “This election cycle is kind of like the Wild West. There’s so much money, I have to think it can’t be good for our political process. But … those are the rules. And we have to play by those rules.”
So does her dad, who last spring said he was ready to drop $10 million, through the Ending Spending Super PAC, on a national ad campaign to defeat Obama. It would make him one of the largest individual or group players in the election, with his fund spending more money than, for example, the Super PACs of the Service Employees International Union, Planned Parenthood, and the National Association of Realtors combined. Baker asked for proposals from several political media consultants. Ricketts zeroed in on Fred Davis of Strategic Perceptions, a colorful and controversial strategist known for such ads as the infamous “I am not a witch” declaration by Delaware Senate candidate Christine O’Donnell. The decision would get Ricketts more attention than he’d ever dreamed — though not in the way he’d hoped — and prove Laura Ricketts right. This election is like the Wild West, and it’s not clear who the sheriff is.
After preliminary meetings with Davis, Ricketts’s team, which included sons Peter and Todd, along with Baker, asked him to present his plan in a May 10 meeting in Chicago. The 50-page proposal, aimed at the defeat of “Barack Hussein Obama,” suggested going back to a strategy proposed and rejected by John McCain four years earlier: Tie the President to the Rev. Jeremiah Wright, the fiery African-American preacher at a church Obama used to attend. The proposal described the President as a “metrosexual black Abraham Lincoln” and began with a quote from Ricketts himself: “If the nation had seen that ad (an anti-Wright spot McCain rejected), they’d never have elected Barack Obama.” No decisions were made at the meeting, which then turned to a campaign to support Nebraska’s Deb Fischer, which Ricketts hired Davis to do.
Ricketts himself wasn’t at the meeting. But before he could respond to the proposal, one of the six participants in that room leaked a circulating copy to the New York Times. The front-page article on May 17 — and subsequent political firestorm — left a shocked Ricketts defending against charges of racism and dirty politics. In the story, Baker said the family had made no decisions on the plan. Says Davis: “Different people in that meeting had different recollections of what happened.” The next day, after Mitt Romney said he “repudiated” the plan, Baker released the following statement: “[Ricketts’s] efforts are and will continue to be focused entirely on questions of fiscal policy, not attacks that seek to divide us socially or culturally.” The imbroglio was a stunning example of how much control the political parties and candidates had lost over their own messages.
For Ricketts, the fallout was immediate. Some Ameritrade customers canceled their accounts in anger. Says Fred Tomczyk, Ameritrade’s CEO: “TD Ameritrade does not endorse the personal views of its shareholders or individual candidates for public office.” DNAinfo.com came under scrutiny, and Ricketts wrote a memo to the staffers assuring them that “[a]lthough I feel a strong obligation as a citizen to engage politically … I feel equally strongly that my personal politics should have absolutely no impact on your work as objective, fair-minded journalists.” It didn’t help that DNAinfo.com had just announced it was expanding to Chicago, of all places, where presumably it will cover such big local stories as the potential renovation of Wrigley Field.
Negotiations over that work broke off abruptly as a furious Mayor Rahm Emanuel, Obama’s former chief of staff, stopped taking Tom Ricketts’s calls. Cubs fans — many of whom are Obama supporters — expressed disgust with Joe Ricketts’s affiliations. Many noted the contradiction between Ricketts’s antigovernment approach and the fact that his children’s main business was in large part dependent on getting local government subsidies.
The episode highlighted how difficult it is for Ricketts to argue against public subsidies with a straight face. The Ricketts family had already benefited from public assistance in 2010, when the city of Mesa, Ariz., approved a referendum to build a new spring-training facility for the Cubs using the city’s enterprise fund and, if needed, the sale of 11,000 acres of undeveloped farmland.
Tom Ricketts admits that the blowup was “noise that we didn’t need,” but says, “In the end, I’m not too worried about it. We’ll get through all this. We all have a long time horizon.” That’s a good thing; more than three months later, the mayor and Tom Ricketts still have not spoken.
Nor will they soon, it’s safe to say. On Sept. 17, Ricketts’s Ending Spending Action Fund unveiled a major new multimedia advertising campaign set to run both in the battleground states and on national cable networks. Although Fred Davis wasn’t part of this campaign, another person well versed in attack videos was: Steve Bannon, the political filmmaker who has been executive chairman of Breitbart, the controversial political group, since Andrew Breitbart’s sudden death in March.
Linked to the website WhyIChangedMyVote.com, the ads feature interviews with regular Americans who voted for Obama in 2008 and now, disillusioned, have shifted their hopes to Romney. The spots are sober and depressing — but offer few specifics about what might change in a Romney administration. One of the subjects, a former nurse from Illinois named Jodi C., says, “There are two choices; one leads to bankruptcy,” and calls this “the most important election in my lifetime.” It will be interesting to see if Ending Spending will make a difference. Ironically, though, it doesn’t seem as if the ads will have anything to do with ending spending on the campaign. That, thanks to Joe Ricketts and others like him, continues unabated.
This story is from the October 8, 2012 issue of Fortune.