Talking to Chicago Cubs Co-owner Laura Ricketts, a Big-Deal Democrat in a Family of Big-Deal Republicans

Chicago Cubs co-owner Laura Ricketts. Photo: Tone Stockenstrom

That’s why I was looking at you like that,” Trudie Acheatel, a Chicago Cubs fan, is saying. She gazes up admiringly, from beneath a bucket hat loaded with Cubs pins, at the sparkly logo pendant worn by Cubs co-owner Laura Ricketts. “I wasn’t staring—”

“Oh, I didn’t notice,” Ricketts interjects. She and two of her three brothers, Tom and Todd, are on a small stage at the Sheraton Chicago, finishing up a talk at the annual Cubs convention, a rowdy town hall where fans cajole and encourage the owners. The Cubs haven’t won a World Series since 1908 and haven’t even been there since 1945, but in the nearly six years since the Ricketts family bought the team, they have invested and rebuilt, and this year the Cubs have their best chance in a long time. “I’m envious of your hat!” Ricketts tells Acheatel.

My hat!” the woman says in a thick Chicago accent. “Really, what you have done to this team, I am so excited.” Ricketts thanks her before turning to a woman who’s presenting a book on Wrigley Field to be signed. “This is a 40-year Cubs fan!” Ricketts shouts in the general direction of her fiancée, Brooke Skinner, a brand strategist at Twitter. “Can we get a pen?”

Ricketts — in a knee-length leather skirt, boots, and blue blouse — could pass for a politician. And in fact, a few minutes later, when Todd and I duck into a meeting room beneath the hotel kitchen, he tells me that Laura, as a kid, “wanted to be president — she even put on a tie.” She instead grew up to work behind the scenes, like the rest of her family. Her father, Joe Ricketts, is the billionaire founder of TD Ameritrade, and Joe and Todd run the huge GOP super-PAC Ending Spending. Her third brother, Pete, is the very conservative governor of Nebraska, who opposes gay marriage. Laura is the outlier Ricketts: a liberal lesbian activist who was one of Barack Obama’s top LGBT bundlers and is the chair of LPAC, which aims to organize lesbian donors into a power bloc.

Laura soon disentangles herself, and we head upstairs to a hotel suite to talk. It’s 10:30 a.m., and she kids me: “Bud Light? They’re our beer vendor, so I have to offer you one.” Ricketts adopts voices for comedic effect: gruff for her dad, boisterous for a gay friend. Now it’s faux announcer: “Would you like a Bud Light? Absolut?”

She settles on the couch. “It’s true,” Ricketts says when reminded of her childhood ambitions. “When I was 5, I wore a tie and I wanted to change my name to Larry, which probably tipped my parents off that I was gay.” Today, she says, she can’t imagine running for office. “I don’t really like politics, to be honest,” she says. “But it’s other people making decisions about my life, and my country, and my child’s education … I wish we didn’t have so much money in politics, but that’s not the world we live in. If we don’t play here, we forfeit. And I’m not willing to forfeit my rights.”

Laura was an all-star softball player in the years after Title IX, the only daughter in a house full of boys. “We had a very male-dominated household,” she says. “Now I’m in baseball and politics, and I think it helped me feel really comfortable.” They weren’t rich, but in 1975, her father co-founded First Omaha Securities, one of the first discount brokerage firms, and built a fortune. “I would not say my dad doesn’t have an ego. He’s big. He thinks big, he dreams big,” she says. Yet she draws a distinction between his political approach and hers with LPAC: “It’s not your father’s super-PAC — specifically, it’s not my father’s super-PAC,” she says, “in the sense that a couple of people are giving a lot of money. This is really more a movement … you can give $5 and I’ll give $5,000, but we’ll get a thousand of you to give $5, and we’re all speaking with the same voice.”

Laura Ricketts says she wasn’t out to herself, let alone her family, for a long time. “I wasn’t gay! I just kept falling in love with my best friend, that’s all,” she says, laughing. Only when she returned to Chicago after law school did she figure it out. She sat her parents down the day after Thanksgiving and delivered a statement she’d rehearsed. “I just said, ‘There’s something going on with me, it’s been going on for a long time. I’ve tried to deny it, I’ve tried to ignore it, but it’s just who I am.’ ” She was in her early 30s.

It was quite a dramatic time,” recalls Joe Ricketts, who broke his custom of declining interviews to talk about his daughter. “I had known many people who have been gay, and their lives were tormented — I’m 73, it was a different generation — but the thing that I didn’t want to have happen was for my daughter to be tormented.” (He sums up his views as “Heterosexuals and homosexuals should be treated equally under the law, given the same opportunity and respect. I don’t believe that you can change the definition of marriage.”) “I said she was born that way, a child of God. I told her to keep her head high and demand respect.”

Laura picks up the story: “You’re a leader,” she says her father told her. “And you can help other young women to come out. You gay people don’t know how to market your cause. You need to do micromarketing — you need to get on the ball!” And then, she says, “He said, ‘You always be proud of who you are. Because I am.’ ” She pauses for a moment, chokes up. “And then he said, ‘If anybody ever gives you trouble you tell me.’ ” She apologizes, dabs her eyes. “I said, ‘Because you’re going to beat them up?’ He was like, ‘Oh, no. I would hire somebody to take care of it.’ 

She became politically active when George W. Bush proposed a constitutional ban on same-sex marriage in his 2004 State of the Union speech. She soon got involved with Lambda Legal, where she realized how few women were at the LGBT events she was attending. When a group began to pursue marriage equality in Illinois in 2012, she helped launch the campaign — and turned to her dad and Todd for help. “I’m hesitant to say much, because it’s his business, but I asked my dad to be supportive, and he stepped up,” she says. (He confirms that he wrote a check.) James Bennett, Lambda Legal’s Midwest regional director, says that “in Illinois, it arguably wouldn’t have happened without her.” She also became a major bundler for Obama and co-chaired the DNC’s LGBT leadership council.

What does her family think of her Obama support? “I don’t think they like it!” Ricketts says, laughing. “They don’t! Todd and I joke that for some candidates we should just not get involved, because we offset our contributions. He had a fund-raiser for Mitch McConnell, and I was like, Ugh — you know I have to do something for Alison Lundergan Grimes now.” Her brother Pete explains that there are things they can talk about: “A lot of Laura’s and my conversations about politics are tactical conversations, aspects of fund-raising and things like that.” As Todd tells it, their mother had a rule: “You can fight in the house, but when you go out in public, you remember you’re a family.”

They’ve followed that rule, but it hasn’t always been easy. In 2012, the New York Times revealed “the Ricketts plan,” a proposal by GOP strategist Fred Davis for Joe’s super-PAC to spend $10 million tying Obama to Jeremiah Wright and calling him a “metrosexual, black Abe Lincoln.” It was bad for the family — the siblings had been negotiating for public funding to renovate Wrigley Field, the Chicago Sun-Times reported that Rahm Emanuel was “livid,” and the deal fell apart. Laura today says, “It was an opportunity for the Obama campaign, and it was used. We all know how those things go.”

It’s a common question put to Ricketts, how she gets along with her family. It’s also one that strikes her as a little bit stupid. “I don’t think we’re unlike any other family. It’s just that we have the capacity to organize and contribute in ways that other people maybe don’t,” she says. “I just say [to people], do you agree with everything your brother thinks? No. Was your family all about marriage equality when you came out? No. So?”

*This article appears in the April 20, 2015 issue of New York Magazine.

Talking to Chicago Cubs Co-owner Laura Ricketts