If you live outside of Chicago, you probably haven’t heard of Todd Ricketts. But we in the city know him well. He’s a member of the family that owns the Chicago Cubs; he and two siblings make up the board. He also happens to be the finance chair of the Trump Victory Committee, a joint effort of the Republican National Committee and the Trump campaign, which makes him the chief fund-raiser for Donald Trump’s reëlection. At one point while reporting this story, I reached out to a friend of the Ricketts family, who chided me in an e-mail. “No one wants to say anything good about the Rickettses,” he wrote. “They are rich and republican. Is there a combination that more connotes evil in the imagination of progressive news readers?” But this is not about being rich or a Republican—though those are part of who Ricketts is. It’s an effort to understand an owner of a major-league baseball team who has chosen to work for the reëlection of a President who refuses to condemn white supremicists, and routinely stokes animus toward Black people and immigrants. It feels antithetical to everything the sport is—or, at least, what it aspires to be.
It’s hard these days to be a sports fan and not get embroiled in questions of politics. Ricketts’s spin in Trump’s orbit has already faced pushback in Chicago. After a Trump fund-raiser last summer, where Ricketts invited big donors to Wrigley Field for a game against the St. Louis Cardinals, Eric Zorn, a columnist at the Chicago Tribune, explained why he had renounced his support for the team, writing, “I’m not mentally gymnastic enough to believe I can support the Cubs but not the Ricketts family agenda.” Mark Jacob, who was hired by the Cubs to create a photo book on the history of Wrigley Field, told me he’s boycotting the team. “If you support the Cubs at this point,” he said. “You’re putting money in the Rickettses’ pockets which they’re using to help get Trump reëlected.” And this past June, the Chicago Sun-Times, in an editorial titled “A Cubs Fan’s Dilemma,” wrote, “What are you to do if you’re a fan of the Chicago Cubs but the team’s owners include a guy who’s leading the effort to reëlect the most divisive, destructive and incompetent president in modern American history? We’d say there’s always the White Sox.”
On the national stage, Ricketts, who’s fifty-one, avoids the limelight. After some deliberation, he declined to talk with me. His public-relations person—whom Ricketts hired shortly after I reached out for an interview—told me that he’s not “an outward person.” He’s flown so far under the radar that when I called a major Republican donor and told him what I was working on, he said, “Todd Ricketts? Who’s that?” It took him a minute to place the name. Indeed, since taking his role as Trump’s chief fund-raiser, he’s made only one public appearance that I could find: on local radio—and part of that event was to talk about the Cubs. One person described his role “like the professional insider”: “If you make headlines it’s a bad thing.”
Ricketts grew up in Omaha, Nebraska, in a family of modest means. According to a memoir written by his father, Joe, they didn’t have money for extended vacations—once, when Todd asked for sixty-nine cents to get a hamburger at Burger King with his friends, his father told him that they needed to eat what they had at home. The family’s economic fortunes changed, though, when their father founded what would become Ameritrade, an early entrant in the field of companies that allowed everyday investors to buy and sell stocks. He ultimately took the company public, in 1997, and became a billionaire. In 2009, Ricketts and his three siblings purchased the Chicago Cubs, for roughly nine hundred million dollars, with money they received from their father. Seven years later, when the Cubs won their first World Series in a hundred and eight years, an estimated five million revellers celebrated in downtown Chicago, the seventh-largest human gathering in world history. The Ricketts were local heroes.
By then, Pete, the eldest sibling, had moved back to Nebraska, where, as a conservative Republican, he won election as governor. Two years later, he would win a second term, and soon stepped down from his position on the board of the Cubs. Laura, the lone sister, is an outlier in the family; she’s a major Democratic donor and contributed to Hillary Clinton’s campaign. Tom, the second-oldest, has remained out of politics and runs the day-to-day operations of the Cubs as the club’s chairman. Todd, the youngest, has at times felt overlooked. Shortly after the Rickettses bought the team, Todd e-mailed his father and older brother Pete complaining that Tom seemed to be getting all the credit. Deadspin published the missive: “My kids live in the same neighborhood and go to the same school as Tom’s kids, and I don’t want them to have to constantly [be] explaining that there are equal owners when they are told that their uncle owns the Cubs. The reason I am so sensitive to this is that even today I feel as though my input and ideas are disregarded among our family, just as they were when we were kids.” As if to underscore his relative anonymity, a year later, Todd starred in an episode of “Undercover Boss,” growing a beard and taking odd jobs at Wrigley Field. No employees recognized him.
Todd Ricketts became deeply involved in Republican politics by working alongside his dad, who had staked out a position as a big conservative donor. (One of Todd Ricketts’s friends told me that Todd wanted to talk politics so much that it became difficult to spend time with him.) In 2013, Todd became the C.E.O. of one of the nation’s wealthiest political-action committees, Ending Spending, which his father founded and whose mission is to take on what it deems wasteful government funding. He and his father were, in many ways, a smaller version of the Koch brothers, whom Joe once reportedly called “great heroes.”
In 2013, Ricketts made a political decision that suggested the kind of compromises he was willing to make. That year, the PAC Ending Spending spent four hundred thousand dollars on ads for the Virginia gubernatorial campaign of Ken Cuccinelli, who would ultimately lose to Terry McAuliffe, a Democrat. Cucinnelli, who is now the acting Deputy Secretary of Homeland Security, spoke to Ricketts’s belief in limited government—especially his opposition to the Affordable Care Act—but he also adamantly opposed same-sex marriage and said homosexuality was “against nature and harmful to society.” For Ricketts, whose sister is gay and active in L.G.B.T. advocacy—and whose uncle was gay and died of AIDS—Cuccinelli seemed like an odd political bedfellow. Moreover, that same year, Ricketts personally lobbied four key Republican state legislators to vote to legalize same-sex marriage in Illinois. “Todd is not a ‘single-issue’ voter,” Danny Diaz, Ricketts’s spokesperson, told me in an e-mail. “Todd obviously does not agree with Cuccinelli’s position on same-sex marriage.” One friend of Ricketts’s calls him “a principled pragmatist.”
Scott Walker, the former Wisconsin governor, is close to Ricketts. They bonded at an event at the American Enterprise Institute shortly after Walker signed Act 10 in Wisconsin, which reduced collective-bargaining rights for most state and municipal workers, including all teachers. Ricketts told Walker he admired what he was doing in Wisconsin—and so, when Walker faced a recall, Ricketts and his parents came to Walker’s aid. Ricketts held a fund-raiser, serving Wisconsin beer and bratwurst at his home in a suburb north of Chicago. “We get wonky, geeky, about policy,” Walker told me.
Ricketts and Walker, it turned out, also shared a love for baseball and for Harley-Davidsons. Walker described Ricketts as “low-key,” someone with a modest demeanor. He recalled a time during his short-lived Presidential campaign, in 2016, when Ricketts, who was co-chair of Walker’s fund-raising efforts, joined Walker in the campaign’s Winnebago, electioneering in Iowa. At one point, on the way to a rally at a minor-league baseball park, Ricketts got out to take photographs of a river. When they arrived at the stadium, a staffer realized that they’d left Ricketts behind. “Instead of being ticked off about it, Todd thought it was just hilarious,” Walker told me. He also remembered hearing Ricketts had invested in bikes. “I’m thinking, O.K., did he buy a manufacturing company?” Walker recalled. And then he laughed. He discovered that Ricketts, who already owned a pizza parlor, had bought a local bike shop.
After Walker ended his run for the Republican nomination, Ricketts reportedly helped raise money for a political-action committee called Our Principles, which was established with the singular purpose of derailing Trump’s nomination. Ricketts’s parents contributed $5.5 million to the PAC, which ran a particularly scathing ad; it featured women reading sexist comments uttered by Trump. (“Look at that face. Would anyone vote for that?”; “That must be a pretty picture, you dropping to your knees.”) Trump, as he’s apt to do, fired back in a tweet: “I hear the Rickets [sic] family, who own the Chicago Cubs, are secretly spending $’s against me. They better be careful, they have a lot to hide!” But, as with many who opposed Trump’s nomination, the Rickettses came around.
During Trump’s campaign, Todd Ricketts spearheaded fund-raising for the super PAC Future 45 and for a like-minded nonprofit, 45Committee, which together raised $73.6 million and which produced ads, not without irony, attacking Hillary Clinton for betraying women. Politico reported that 45Committee targeted donors who felt uncomfortable supporting Trump publicly. “Ricketts’ pitch to these donors,” according to the story, “focuses on the fact that one of the pro-Trump groups he’s fronting can accept unlimited checks while keeping its donors’ names secret.” Early in his term, Trump rewarded Ricketts for his support, nominating him to become the Deputy Secretary of Commerce, but Ricketts, unable to disentangle his financial interests to satisfy ethics rules, withdrew his name from consideration.
Walker told me that he and Ricketts are thrilled with what Trump has delivered: cutting taxes, making conservative judicial appointments, and pushing for deregulation. “This is precisely where Todd’s heart is at,” Walker, who also ended up supporting Trump, told me. “I may not always agree with what he says or tweets but, hey, the guy’s done things he said he’d do.” Walker also pointedly warned that the upcoming election is a stark choice between free enterprise and socialism. “Todd and I have talked about this,” he said. “Look at Venezuela. Look at the bread lines there. We’ve talked about how these socialist policies failed.” Jimmy Kemp, who runs the Jack Kemp Foundation, which is named after his father, the late congressman and Housing and Urban Development Secretary, told me, “One of the top things Todd agrees with the President about is the belief in the free-enterprise system—as opposed to socialism.” A friend of Ricketts’s told me that he has praised Augusto Pinochet, who in 1973 overthrew the socialist government of Salvador Allende, in Chile. The friend told me that Ricketts was dismissive of Pinochet’s ruthlessness. “People die every day,” Ricketts had told the friend.
Ricketts appears to share some of Trump’s rough-edged sensibilities. He’s gone on long rants with friends about Barack Obama being a socialist. He recently appeared maskless at Trump’s indoor rally in Henderson, Nevada. And, earlier this month, the Associated Press reported that Ricketts, along with Vice-President Mike Pence, had been scheduled to attend a fund-raiser in Montana at the home of two QAnon-conspiracy supporters. “Todd was not scheduled to attend that event,” Diaz, Ricketts’s spokesperson, told me. “The finance chairman’s name has been listed on every single invite issued by the R.N.C. or Trump Victory since he was named to those positions, regardless of whether he plans to attend.” Diaz declined to convey Ricketts’s feelings about QAnon.
Last year, the online publication Splinter published e-mails from Joe Ricketts to his children. In one, he suggested that President Obama was a drug trafficker and sex worker. Another e-mail read, “I think Islam is a cult and not a religion. Christianity and Judaism are based on love whereas Islam is based on ‘kill the infidel’ a thing of evil.” At a press conference, Todd’s brother Tom said, “Honestly, I was surprised by those e-mails. Those are not the values our family was raised with.” Joe Ricketts later apologized for his e-mails.
Despite his father’s experience, Todd Ricketts can be surprisingly unfiltered. In comments on his Facebook page, Todd referred to COVID-19 as the “the kung flu”—weeks before Trump used the demeaning phrase at a rally in Tulsa. In a post of a video in which New York Mayor Bill de Blasio urged residents to call the city if they witnessed large gatherings of people, Ricketts commented, “All snitches will be given priority when applying for jobs as security guards at the concentration camps that will be opening later this year.”
In the wake of George Floyd’s murder, a hundred and fifty current and former Black baseball players formed the Players Alliance, in large part to address the lack of racial diversity in the sport. When I reached out to players associated with the alliance about Ricketts, no one would talk. A spokesperson told me that they declined my calls because the players want to maintain good relations with the owners. On opening night, players for the Washington Nationals and the New York Yankees took a knee, this in a sport that unlike, say, basketball, has remained pointedly apolitical. The Cubs, as an organization, has shown support for the alliance’s goals. The club’s president, Theo Epstein, has publicly acknowledged the need to hire more Black people in front-office and coaching positions, and, on the marquee outside the stadium, the club displayed the plea “End Racism.”
Trump, of course, has regularly denigrated immigrants and Black people. In 2017, he called any athlete who takes a knee to protest racial inequity a “son of a bitch.” Nearly a third of baseball players are foreign-born—though most have remained silent on matters of public concern. An official at the Major League Baseball Players Association told me that many foreign-born players, given the times, fear that if they speak out, immigration authorities will come after their families. The league has fallen woefully short in hiring Black managers and front-office executives. Black players make up only 7.5 per cent of major-league rosters, the lowest numbers in twenty-nine years; the Cubs, who lost in the first round of the playoffs this year, had four African-American players on their playoff roster.
Ricketts’s spokesperson periodically sent me clippings about all that the Cubs were doing for social justice, including a photo the team tweeted out of players in Black Lives Matters T-shirts. The President, of course, has called Black Lives Matter “a symbol of hate.” I asked where Ricketts stood on the Black Lives Matter movement. Through his spokesman, Ricketts said, “I support the Cubs players and the things they’re doing to promote unity—and that includes supporting their efforts on Opening Day to bring people together.” When I received this statement, I was reminded of what Doug Glanville, a former Cubs outfielder who regularly comments on the intersection of politics and culture, had written in an essay for the New York Times: “Ambiguity has always been a friend to racism.” As for the Cubs, their spokesman, in an effort to presumably distance the team from Ricketts’s political activities, simply said, “Tom [Todd’s brother] is the executive chairman.”
Maze Jackson, who hosted a talk show on Chicago’s WVON, a radio station with a predominantly Black audience, met Ricketts two years ago, at a reception at a Wrigley Field skybox. As Jackson tells it, he and Ricketts immediately connected. “Todd is pretty direct,” Jackson told me. “He’s a down-to-earth guy, not a lot of pretense—and pretty open to listening. . . . One of the things we agree on is that there needs to be a different path to revive the Black community.” Ricketts is a big booster of Opportunity Zones, which have been championed by Kemp and which Trump included in his tax cuts; they offer financial incentives in the form of tax breaks for people willing to invest in certain distressed neighborhoods. “The challenge in our conversations,” Jackson told me, “is how do you address the systemic racism. Sometimes Todd would say, ‘How come you guys can’t just . . .?’ and I’d explain we haven’t had the opportunities.”
Recently, the players on the W.N.B.A.’s Atlanta Dream have pointedly taken on one of the team’s owners, Senator Kelly Loeffler, who chided the team for honoring the Black Lives Matter movement. No one expects that to happen here in Chicago, especially because, unlike Loeffler, Ricketts has avoided public appearances, let alone public confrontations. Even if Ricketts doesn’t face that kind of reckoning, he will forever be associated with a President who by most measures has set aside any sense of decency and has insistently kicked at the very legs of our democracy. (When asked whether he agrees with Trump’s assertion that if he loses, the election was rigged, Ricketts declined to respond.) “If you’re publically on the record for Trump, you cannot walk that back,” Joe Walsh, a former Republican congressman who is regretful about initially embracing Trump, told me. “You need to be held accountable. Forever.”
Last summer, Ricketts appeared on Jackson’s radio show, shortly before he hosted a big fund-raiser for Trump. Jackson pressed him on his embrace of the President. “A lot of people get hung up on the rhetoric and twitter and things,” Ricketts told Jackson. “But when you drill down on the policy he’s executing on, you know, most of the people in this country feel like we need to reform our immigration process, most of the people think we need to reform our trade agreements, most of the people are in favor of rethinking how we do our tax policy.” It’s as if Ricketts is asking us not to listen to the words of our President.
Earlier this summer, Ricketts had much to feel good about. Trump raised a hundred and sixty-five million dollars in July, about twenty-five million dollars more than Biden and the Democrats. It’s difficult to know what role Ricketts played in this haul, but in an e-mail Ronna McDaniel, the R.N.C. chair, called him “a fantastic fundraising partner.” Recent weeks have brought some undoubtedly sobering news. In August and September, the Biden campaign posted back-to-back record-breaking fund-raising totals, outraising Trump by nearly three hundred million dollars. And in a front-page story last month, the Times reported that the Trump campaign had spent so much money in the first half of the year that they had little left to spend on television advertisements. There are also reports that some big donors who had contributed to Trump’s first campaign are either sitting this one out or giving less. One big-monied donor, Thomas Peterffy, told me he worries Trump has become “concerned more about his success and achievements than he is about the country.”
