The Ricketts Family Owns the Chicago Cubs: Who Are These People?

The four children of Omaha billionaire Joe Ricketts hold the fate of the Chicago Cubs—and of Wrigley Field—in their hands.

The Ricketts Four at Wrigley in May (from left): Todd, Pete, Laura, and Tom   Photo: Taylor Castle; Hair and Makeup: Jen Brown

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The Ricketts on vacation

Photo: Courtesy of the Rickettses

The family on vacation in 1992, five years before Ameritrade went public

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.

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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.”

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