On a spring Saturday shortly before noon, Wrigleyville is astir. The bro bars on Clark Street fling open their windows, belching out waves of music and stale beer. Red Line trains shriek into the Addison stop, disgorge blue-and-red hordes, and then clack away, kicking sparks. Joining the throngs who are making their way to the ballpark is a lanky guy in his 40s with thinning hair and a round, amiable face.

As he circles the upper deck, wearing pleated khakis and a blue lightweight fleece adorned with a Cubbie patch, he looks like any other Chicago dad off to get his kid a hot dog. But then he begins saying hello to strangers and handing out baseballs signed by the likes of Starlin Castro and Anthony Rizzo. Only at that point do most people seem to recognize him: Tom Ricketts.

While his family’s purchase of 95 percent of two of the city’s most sacred institutions—the Chicago Cubs and Wrigley Field—happened four years ago, Chairman Ricketts and his clan still aren’t well known or understood here. When they do make news, it isn’t always flattering. The 2010 appearance of Tom’s younger brother, Todd, on the CBS reality show Undercover Boss, in which he was canned for poor toilet-scrubbing skills, was slightly cringe inducing. But that was nothing compared with the public relations disaster that followed a New York Times report last year that Tom’s father, the conservative billionaire Joe Ricketts, was considering a $10 million preelection ad campaign linking President Obama to “incendiary comments by his former spiritual adviser.”

Joe Ricketts, 72, who has retired to Little Jackson Hole, Wyoming, isn’t giving interviews. But his four children—Pete, 48, who lives in Omaha, and Tom, Laura, and Todd, 47, 45, and 43, respectively, who live in the Chicago area—all agreed to speak to me for this story. (All four are on the Cubs’ board of directors.) Interviews with them, with friends and colleagues of Joe’s whom he authorized to speak for him, and with contacts in Chicago and in the family’s home state of Nebraska help explain the family’s approach to the high-stakes negotiations with Wrigleyville rooftop owners that they’re currently embroiled in—an approach that has puzzled some and enraged others.

As you know, in April the Rickettses announced the hard-won framework of an agreement with the city for a sweeping $500 million renovation to the historic but crumbling Wrigley Field and its environs. But when Wrigleyville rooftop owners hinted at suing to protect their views, Tom Ricketts dropped a bombshell: If people continue to stand in the Cubs organization’s way, it may have to look at moving the team to the suburbs.

Is the family really willing to yank the Cubs from hallowed Wrigley and move them to suburban Rosemont, Schaumburg, or Cicero? Will they risk a move that instead of robing the Ricketts name in glory would cloak it in ignominy? And more fundamentally: What drives these superrich Nebraska natives? What values shape their decisions? Who are they beyond the cardboard bios put out by their public relations team?

To understand the Ricketts family, you have to start not at the ballpark, or at their gleaming new offices in a red-brick building just off Clark Street, or at a press conference, or on the tree-cool streets of Wilmette, where Tom and Todd live. You have to travel to Nebraska City.

To reach it, you drive down Interstate 75 about an hour south of Omaha, along the serpentine Missouri River; past the cornfields that blur by for mile after waving mile, like a vast golden ocean; past long stretches of boxcars that rise blue-black against the horizon and clatter so slowly across the plains that they seem almost motionless; past the billboard that asserts “America Needs Farmers.” You swing onto North 11th Street, where the closest thing to a skyline is a cement grain elevator hung with little lights that shine at night like dangling pearls. And finally you enter the oldest incorporated city in Nebraska, population 7,200, best known for its AppleJack Festival in September, where around 40,000 folks from the region gather to enjoy parades, a carnival rides, and a quilt show.

John Joseph Ricketts came into the world here in 1941, the oldest of four children born to Florence and Donavon Ricketts. Don, as he was known, was a carpenter, an exterminator, a small-business man, a farmer, and a staunch Catholic—“a very, very hard worker [who] was very strict with his children,” Laura says.

Joe got his first job in third grade, cleaning stools at the county courthouse. At St. Bernard’s Academy, he met his future wife, Marlene Volkmer. In 1959, he went to Omaha to attend
Creighton, a Jesuit university, working first as a janitor and then as a hospital orderly to pay his tuition.

The young man’s worldview was informed by the conservatism that surrounded him. “He has . . . bedrock Midwestern values, which is to say a real belief in hard work and that if you apply yourself and work hard, you’ll get results,” a close family friend and associate tells me. “He’s a very straightforward guy. He doesn’t play games with people. He lets you know how he feels, positive or negative, and he appreciates the same from people who deal with him.”

In 1963, when he and Marlene were both 22, they married. “There’s a picture of the happy couple,” says Michael McCabe, pastor of St. Mary’s Catholic Church, pointing to a framed photo in the church entrance. “Flush with excitement, ready to tackle life.”

The initial plan was that Marlene, a teacher, would work while Joe finished college. But in 1964 she became pregnant with Pete. A year after he was born, Tom came along. “The bills started piling up,” Joe recalled in 2000 in a rare interview with a local weekly newspaper. “I had to reduce my academic effort to be more in line with my ability to pay, so I went to school part time.”

It took Joe nine years to get his bachelor’s degree. In retrospect, he said, he was glad for the decelerated pace. “[It] helped me to learn how to organize my mind in figuring out problems,” he said. “I had to learn a lot of discipline.”

During those years, he found his calling. Working as a credit analyst at Dun & Bradstreet, he said, he “saw the fun and excitement that business people had. . . . I decided I wanted to have my own business. But I didn’t have any money.”

He subsequently took a job as a stockbroker at Dean Witter but quit to strike out on his own as soon as he earned his degree. In 1975, the year that the U.S. Securities and Exchange Commission deregulated broker commissions, Joe cofounded something new: a discount brokerage. First Omaha Securities, as it was called, allowed investors to buy and sell securities for lower commissions than old-school full-service brokerages charged. It was a prescient move that would make possible all that followed.

In those days, the business came first. For Joe, that meant working 80-hour weeks and plowing virtually every spare penny back into the company. For his children, it meant that vacations were virtually nonexistent. Paper routes paid for bikes. The family car was a puke-green Ford station wagon or some other hand-me-down from a relative, his children recall.

The decor of their house—a white dormered three-bedroom dwelling on Hickory Street, perched on a hill in an Omaha neighborhood with a mix of middle- and upper-middle-class homes—“was probably outdated by 10 years,” Laura laughs. “It was falling apart.” When the dishwasher broke, as it often did, it stayed broken until the family could scrape together repair costs. “We may have propped a chair against the oven door for a while to keep it closed,” Laura adds.

The ultimate, however, was Marlene’s decision to use plastic picnic-table covers with a 1976 bicentennial theme as curtains in the bedroom that all three boys shared, recalls Pete. “We definitely were the poor family in the neighborhood,” Todd says. “I tell people that one of the reasons I have a bike shop today (see “Take a Ride with Chicago’s Craziest Bicycling Subculture”) is that I never had a bike as a kid.”

The children took on familiar birth-order roles. “Pete, the oldest, was all about maintaining the status quo,” says Todd. “Tom was more of a diplomat in his personality, as he kind of still is today.” Laura—“the smart one,” she describes herself—caught “the brunt of the teasing from the boys,” says Pete.

Sibling disputes often ended in calls to their mother’s office (Marlene was by now working as a secretary at Joe’s business). Todd recalls with a laugh that after he made Laura cry about something, “she called my mom, but my mom wasn’t around, so she got my dad. I was probably seven and Laura was nine. My dad tells Laura, ‘Put Todd on the phone.’ And he’s like, ‘When I get home you will be spanked.’ There was no debate. No defense.”

As a father, Joe Ricketts was much like he was as a businessman: imposing, tough, gruff, intolerant of disobedience, and stingy with words. “I think that what made us not cross him is that there weren’t big conversations,” says Todd. “It was, ‘You’re going to do this.’ ”

“He was not one to be playful very often,” agrees Laura. “On Saturday mornings, I remember him coming down, and we’d be watching cartoons and eating cereal, and he’d say, ‘OK, now this is your job for the day. Boys, you’re doing this. Laura, you’re doing that.’ He was just very much like, You need to work to make your way in this world, and we’re not going to spend Saturday watching TV.”

All four Ricketts children attended West Side High, a public school that at the time was dubbed Hollywood High. “It was where the rich kids went,” says Henry Cordes, an Omaha World-Herald reporter who has covered the family.

But unlike many of their classmates, the Ricketts boys worked summers—Pete and Tom at Burger King and Todd at Kentucky Fried Chicken. (Laura got a pass.) When it came to college, Joe showed rare permissiveness. He would pay their way to any school they wanted, with one caveat. “It had to be far enough away that we couldn’t come home to do our laundry,” says Todd. “My mom [would have] hated that.”

Pete chose the University of Chicago for its strong biology program. Though he didn’t know it at the time, he was blazing a trail to the Second City. Both Tom and Laura followed him to U. of C., and Todd headed to Loyola University.

After college, the Ricketts siblings stayed in Chicago and remained as tight as ever, hopscotching their adopted city together. “Every year we [the three boys] would move just to try new neighborhoods,” Tom tells me from the owner’s box as a game grinds on. “Then, one year, probably around 1990, Pete and I just moved up here [to Wrigleyville].”
They became roommates in a quintessential neighborhood pad above the Sports Corner Bar & Grill at the corner of Sheffield and Addison Avenues. They couldn’t have chosen a more Cubs-centric spot. “The vendors would be yelling, like, 10 feet from my head,” Tom recalls. “We were just immersed in Wrigleyville.”

Immersed to the point that the brothers went to the basement of the Cubby Bear to pay rent to the bar’s proprietor, George Loukas—one of the rooftop owners with whom Tom now finds himself locked in a stalemate.

One day in the Wrigley Field bleachers—where “before the tyranny of the two-beer limit you could go down and get as many beers as you wanted and just hand them up,” Tom recalls—
a group of college-age women sat next to him and some friends. Tom took note of one young woman in particular. “We started talking,” he says. “And now we’ve got five kids.”

In the years that followed, the siblings went their own ways for a time. Tom, who had gone on to earn his MBA at U. of C., moved to Detroit, where his wife-to-be was doing her medical residency. Pete started working for his father, whose company had been renamed Ameritrade Clearing, rising to COO (Joe was the CEO). Laura earned her law degree from the University of Michigan and then began practicing in Chicago at Schiff Hardin. After a brief period at Ameritrade, Todd moved to New Jersey to work for a securities firm called Knight Capital.

Meanwhile, Joe was betting big on tech. In 1988, a year after Todd started college, Ameritrade became the first brokerage to execute trades using touchtone telephones. In 1995, it bought one of the first firms to allow customers to use the Internet for trading. That may seem like a no-brainer now, but it wasn’t at the time. “This is not Steve Jobs or Bill Gates coming out of the East or West Coast or some Ivy League school,” says a family friend of Joe’s. “Yet he was a very shrewd and keen appreciator of technology very early on.”

As CEO of a prospering company, Joe clearly had fewer money worries now than when his children were small. But he had yet to hit the ultimate payday of any company founder: the day the place goes public. In 1997—at which time his children were in their late 20s to early 30s—that day finally came. By 1999, the boy from Nebraska was worth some $2 billion, joining fellow Omahan Warren Buffett as one of the richest men in the country.

Joe began indulging in the finer things. In 1998, he snapped up a breathtaking 1,300-acre ranch in Little Jackson Hole. There he went on to raise bison; his subsequent business venture, High Plains Bison, now ranks among the nation’s top producers. He began raising Percheron draft horses so beautiful that they clip-clopped in the Tournament of Roses parade.

In 1999, Joe bought the most expensive house ever sold in Omaha: a $7 million 17,000-square-foot estate with a six-car garage and a 1,600-square-foot pool. He topped off the spending spree in 2006 with the purchase of a 78th-floor penthouse in the new Time Warner Center off New York City’s Central Park for a cool $29 million

By then, however, he was no longer Ameritrade’s CEO. After the stock price plummeted nearly 94 percent in the dot-com crash of 2000, a Merrill Lynch executive named Joe Moglia was brought in to replace him. A series of acquisitions and a merger with TD Waterhouse followed. The company, now called TD Ameritrade, recovered, as did Joe Ricketts’s net worth.

As deeply conservative as his father, Pete left Ameritrade in 2006 to run for the U.S. Senate. He was pushed even further right during a vicious primary battle; in the general election, the incumbent Democratic senator, Ben Nelson, won by portraying Pete as a neophyte who was trying to buy a Senate seat with his dad’s money. “He never shook that,” says Cordes. “He had some good things going for him. He’s a pretty nice guy who had done some good things at Ameritrade. But at the end of the day, he was Joe Ricketts’s son.”

Pete’s far-right positions—including vehement opposition to progressive social issues such as marriage equality—put him at odds with his left-leaning sister, a lesbian and staunch supporter of gay rights (and bigtime Obama backer). “We had conversations where I’m just like, ‘I wish you well,’ ” Laura says. “But we have very different views on some really significant issues, and some of them are very personal to me.

“Family trumps politics. . . . I was there election night. But I was also kind of watching out of the corner of my eye all the other Senate races, hoping that, if Pete won, there would be [a] Democrat that would pick up the seat.”

Telling her family that she was gay was not easy. “I waited a long, long time,” Laura says. “When I came out to Todd, I think his response was, ‘Duh. Have you ever heard of gaydar?’ ”

She was surprised and touched by her parents’ reaction. “My mom basically said, ‘You’re still the same person to me. I still love you. You’ll have challenges that I’m concerned about, and your life will be harder than if you weren’t gay. But you’re still the same person.’ ”

To her shock, her father revealed that one of his brothers, who had passed away in the 1980s, had been gay and had died of AIDS. Laura relates that at the time, “one of my dad’s siblings said, ‘What do we do about this?’ And [Joe] said, ‘What do you mean, what do we do? Who cares if he’s gay? He’s dying. We need to be there for [him].’

“My dad said [to me], ‘You’re the best thing that ever happened to the gays!’ and ‘You know, you guys don’t market your causes very well. You’re a natural leader. You should do something to help more young people come out.’ [Laura would eventually do just that, cocreating her own super PAC last year called the Lesbian Political Action Committee.]

“I felt like such a fool for having waited for so long. I have friends who cry when they hear my coming-out story.”

Buying the Cubs was the brainchild of Tom Ricketts. “In one sense, it all seems an extraordinary coincidence,” he says. “On the other, that it was almost fated.”

Shortly after Sam Zell’s 2006 takeover of Tribune, which then owned the team (and owns this magazine), Tom foresaw a chance to pull off the most audacious business play for the family since Papa Joe pushed all his chips in with the Internet. “There was one asset that wouldn’t fit with a private equity firm,” he says. The Cubs.

Though the Ricketts siblings loved the team, not one had expressed the slightest interest in getting involved with pro sports. They all had plenty on their plates. Tom himself, who had settled in Wilmette, was in the midst of building his own investment banking and securities firm, Incapital.

Tom’s reasoning ran deeper than his passion for the atmosphere, the tradition, and the magic of Wrigley. It ran all the way back to Omaha. In the Cubs, Tom saw an opportunity to reclaim something that his father and his family had lost: a business that belonged to them. Ameritrade had been that thing—until it grew so big that it no longer had room. “I thought: This could be the [venture] that stays a family business for a long time,” says Tom, “and becomes a central kind of thing that holds the family together.”

On a practical level, Tom thought that he could run the team better than Tribune, which had spent years saddling the roster with free-agent megacontracts while kicking ballpark upgrades down the road. That short-term mentality, he believed, was not the way to build a winning organization. (He would put that belief into practice by hiring Theo Epstein, the nation’s top baseball exec, known for taking the long view.)

On a gut level, he saw a chance to burnish the Ricketts name in a way that even Papa Joe’s billions could not. “To be a part of a family that brings a World Series champion to these fans,” Tom says, “would be one of the greatest legacies you could imagine.”

The first order of business was persuading the paterfamilias. Joe couldn’t have cared less about Wrigley. He was a businessman with a raft of new ventures in the works (including an online hyperlocal media concern called DNA info), and he was growing increasingly involved in funding conservative causes.

It was to Joe’s bottom-line ethos that Tom appealed. Their initial conversation was not promising. “ ‘Aw, that doesn’t sound like a very good idea,’ ” Tom recalls his dad saying, affecting a gruff voice. “I was like, ‘Don’t say no. Think about it.’ ”

Tom knew he needed a clincher. His solution was ingenious and, in retrospect, ironic. He took his father to one of the very same rooftops whose owners now stand in the way of Wrigley’s renovations. Tom said, “Look at this.”

Joe replied, “Yeah, that’s pretty beautiful.”

“They sell three million tickets a year, win or lose,” Tom told him.

Joe said, “Oh, this is a business.”

With his father onboard, Tom turned to his siblings. They were skeptical. “Major-league baseball is a bit of a good ol’ boys club,” Todd says. “We thought, Well, we’re not connected. We don’t know if we have enough money. It seemed like a one-in-a-million shot.”

Again, the rooftops served as a convincer. “It was a beautiful day, and the place was full, and we just looked out over all of Wrigleyville,” Tom recalls. “And that’s when everybody was like, Yeah, let’s at least try for this.”

Tom had been right: Soon after buying Tribune, Zell announced that he was putting the Cubs on the block. By this time, unbeknown to other interested bidders, Tom had spent months lining up financing, meeting with other major-league baseball owners, and getting the league comfortable with him.

While flamboyant players such as Mark Cuban, owner of the Dallas Mavericks, issued bold pronouncements of their intentions, Tom made sure his family kept a low profile. “You want to be below the radar screen,” says Sal Galatioto, a high-powered sports finance adviser who worked with the family.

When the Rickettses officially entered the fray in 2007, they seemed like dark horses. But the groundwork Tom had laid paid off. From seemingly out of nowhere, the family became the front-runners, then the winners.

It took two years of agonizing negotiations with Tribune to seal the deal. (To fund the purchase, which totaled $845 million, the Rickettses dipped into a family trust that Joe and Marlene had set aside.) First came the credit freeze that followed the 2008 stock market crash; then Tribune filed for bankruptcy. “Lesser men would have thrown up their hands and said, ‘You know what? This is bullshit. I can’t do it,’ ” says Galatioto. “Tom’s style was to grind it out, and he can grind it out with the best of them.”

The Ricketts siblings promptly installed themselves as four of the Cubs organization’s five board members (the fifth is a representative from Tribune, which still owns 5 percent of the shares). As chairman, Tom was on the hot seat. “He has to report to the board just as any executive [does],” says Todd. “Obviously, as a family member, we’re going to cut him a little slack for the first few years. But there have to be results on the field and in the business.”

Results, of course, are what can help keep the Rickettses in control for generations to come. (The siblings have a dozen kids among them; see the family tree on page 2.) “When we bought the Cubs, our time horizon was 80 to 100 years,” says Pete. “I expect that the family will own the team long after I’m dead.”

On one of my walks around Wrigley Field with Tom, he muses on restorations both cosmetic (replacing cement overhangs with terra cotta and chainlink fencing with wrought iron) and structural. The ballpark desperately needs upgrades. The bathrooms reek. The locker rooms squeeze the teams into uncomfortable boxes. And unlike virtually every other team in the major leagues, the Cubs do not have a batting cage where pinch hitters can warm up.

Initially, the team sought public funds by asking for a freeze in the 12 percent amusement tax it pays to the city, the second highest in the major leagues. A deal seemed close—until the May 2012 New York Times story about Joe Ricketts’s potential anti-Obama campaign.

Mayor Rahm Emanuel, Obama’s former chief of staff, went ballistic. The outrage, many said, was more show than anything, the perfect opportunity to bash a conservative entrepreneur for the apparent hypocrisy of seeking public funds while saying that the government was a profligate spender.

The criticism stung the Rickettses. For starters, Joe may have supplied the money to buy the team, but he was not, as many media outlets reported, the owner of the Cubs.

Joe quickly proclaimed that he had nothing to do with the potential ad campaign, which had been pitched by his consultants. Tom and Laura (who had been a top Obama bundler) also denounced it. The damage, however, had been done. “It was horrifying,” says Todd.

Tom kept a cool head. A few months later, he offered a new plan. This time, the team would not seek taxpayer help and would fund the entire renovation on its own. In exchange, it expected to be able to make the repairs it deemed necessary.

While the mayor (who declined to comment for this story) reportedly looked favorably on the plans, nothing in Chicago is easy. A major sticking point arose: the Rickettses’ desire to put a 1,000-square-foot advertising sign in right field that could partially obstruct some rooftop views.

The rooftop owners, led by Beth Murphy of Murphy’s Bleachers, became the face of the opposition, hinting darkly that they might sue if the Rickettses blocked their vistas. (A contract between them and the Cubs, negotiated with Tribune, still has more than a decade left on it.) Wrigleyville residents, meanwhile, complained that the organization’s plans to build a hotel near the park and hold more night games would bring too much noise and congestion. (For details on the proposed changes, see the map above.)

During the marathon negotiations that ensued, Tom’s siblings grew restless. But the chairman remained upbeat and unflappable. That’s not to say his handling of the situation has received uniformly glowing reviews. Some sports business experts say he is too nice—too Omaha—to get what he wants. “Tom is paying the price of being a nice guy,” says Marc Ganis, president of Sportscorp, a sports consulting firm in Chicago. “I think [he] is perhaps disgusted by the blood sport that is Chicago and Illinois politics. It is not part of his DNA to have every matter be a knife fight to the death.”

Ganis’s biggest complaint is that Tom did not play hardball about moving the team to the suburbs. It was not until a City Club breakfast in April—at which Tom announced that he had reached the framework of a deal with the city—that he said he would have to consider moving the team if rooftop owners blocked his proposed signage. He was almost apologetic.

Emanuel scoffed at the idea, as did a number of Cubs observers. “Rosemont is the worst possible location I can ever imagine for a professional baseball stadium,” says Al Yellon, managing editor of the Cubs fan blog Bleed Cubbie Blue. “People do not want to drive to a suburban stadium on weeknights.”

More to the point, critics say, Tom Ricketts has made it clear from day one that he’s loath to move the team. “No one is afraid of Tom Ricketts,” Ganis says. “No one is afraid of the Chicago Cubs.”

Indeed, hanging out with Tom, it’s hard to feel intimidated. Whether it’s listening to a fan’s complaint or posing for pictures with sombrero-wearing dudes at a bachelor party, who slosh beer on him during the game, he is every bit the affable, funny, mild-mannered guy. He almost never raises his voice, nor does he register displeasure, beyond occasionally pressing his lips together and glancing sideways.

Some who have watched him at the negotiating table, however, say not to be fooled. “He’s a smart, very purposeful guy who delivers in a measured and unflappable way,” says Alfred Levitt, a lawyer from Washington, D.C., who helped Tom close the Cubs deal (and is now president of the holding company for Joe’s businesses). “I’m not an expert in Chicago politics. I’ve heard similar comments, that you have to be able to brass-knuckle it or whatever. But I actually think that Tom is an incredibly effective person at getting things done.”

Adds Laura: “This is like his blood, sweat, and tears now.”

I see a flash of what they mean during one of my interviews with Tom. While sitting in his family’s box, perched near home plate, I ask him how serious he is about moving the team. Does he really want his family’s name to go down in history as the owners who uprooted the Cubs from one of the most iconic stadiums in baseball and moved them to . . . Rosemont? Can he live with that?

At first he launches into his boilerplate response: that he doesn’t see it happening, that everyone is close to an agreement, that the family’s proposed $500 million remake is going to keep the Cubs as the state’s third-largest tourist attraction, that when a player catches the last out in the clinching game of a World Series, he will do so in Wrigleyville. “This is not just any old ballpark, and I don’t think we really needed to resort to any crazy type of threats for everyone to feel like they have incentive to save it,” he says. “I think everybody knows this is a huge economic driver for the city [and] the local businesses, including the rooftops. Everybody has an incentive to make sure this goes forward.”

But then his expression changes. All that said, he tells me, his proposals must happen. As for a fan revolt, his answer is a chilling one for those who think a move is impossible. “Overwhelmingly, the people I talk to say, ‘Do what you have to do.’ They really do. Every fan puts winning over Wrigley.”

He pauses. The nice guy returns. “But I don’t think we’re there. We’re going to win the World Series in Wrigley. And everyone will get what they need.”