Cubs chairman Tom Ricketts has said his family's financial support of pro-Trump super PACs is "no big deal." Credit: Evan Vucci; Matt York

During game six of the National League Championship Series, the Ricketts family counted two big wins. The Cubs, the team they’ve owned since 2009, advanced to the World Series for the first time since 1945. The wealthy clan also capitalized on a sizable national TV audience to advance the political fortunes of Donald Trump, whom they’ve supported since he became the Republican nominee in July.

Fans watching the October 22 broadcast of the Cubs’ triumphant pennant clincher got an eyeful between late innings of a commercial critical of Hillary Clinton. The attack ad accused the Democratic presidential nominee of betraying women, claiming that the Clinton Foundation has taken millions of dollars from foreign countries with antiwoman policies and values. The final image of the 30-second spot shows Hillary and husband Bill Clinton speaking at a foundation event with onscreen text reading: the clintons sold out millions of women. The small print underneath the statement notes that the ad was paid for by Future45.

An anti-Clinton ad paid for by the Ricketts-backed super PAC Future45 ran during game six of the National League Championship Series.

Future45 is a super PAC founded by casino magnate Sheldon Adelson and the Ricketts family. Todd Ricketts oversees the fund, which has reportedly raised at least $30 million in the effort to elect Trump, including a $1 million donation from family patriarch Joe, the former CEO and former chairman of TD Ameritrade.

That the owners of the Cubs are funneling fans’ hard-earned money toward an effort to elect Trump—a putative bigot and misogynist, a thin-skinned bully whose platform includes building a wall on the Mexican border, deporting Muslims, and punishing women for having abortions—hasn’t caused so much as a peep among left-leaning supporters of the team. No one yet has stormed the Friendly Confines or ripped up tickets in righteous indignation during a rally at Clark and Addison. Thus far the celebration of baseball’s lovable losers turned World Series favorites has been a bipartisan affair. 

The only real controversy in the run-up to the World Series has had nothing to do with the Cubs. Their opponents, the Cleveland Indians, have faced protests and boycotts stemming from the team’s name and Chief Wahoo logo, which are considered to be insensitive to Native Americans. Op-eds are already rolling in demanding that the American League franchise change its name and face. Meanwhile the news of the Ricketts’s pro-Trump fund-raising and spending this year has gone largely unexamined, aside from a few scattered headlines and a couple irate letters to the editor that were muffled by the day’s Trump-inspired controversy or overshadowed by the Cubs’ on-field successes. 

Not everyone backing Team Trump has been so lucky. Consider the Silicon Valley revolt against Peter Thiel after he recently supported Trump with $1.25 million split between super PAC donations and direct contributions to the campaign. Last week the group Project Include cited Thiel’s support for Trump in their decision to sever ties with tech incubator company Y Combinator, where the tech billionaire holds a position as part-time partner. Others on social media have called for boycotts against Thiel’s former company PayPal. There’s been a similar backlash against Home Depot after the store’s cofounder Bernard Marcus came out in support of Trump.

So what’s keeping progressives who bleed Cubbie blue from seeing red over the team ownership’s financial support of Trump?

It’s true that the Ricketts brood that bought the Cubs in 2009 for $845 million aren’t unified in their politics. The black sheep of the family is Laura, a Democrat and active Hillary Clinton supporter who wore a Clinton cap at Wrigley Field in September just days after it was announced her father would donate $1 million to back Trump. For his part, Cubs chairman Tom Ricketts projects an image of nonpartisanship. But the rest of the clan can be generally characterized as conservative activists donating large amounts of money to ultraconservative candidates and causes. 

The head of the family, Joe, who made his fortune through online brokerage TD Ameritrade, now owns a milquetoast movie production house, American Film Company, though he was also an investor in Dinesh D’Souza’s anti-Obama propaganda film 2016: Obama’s America. He founded the admirable—and distinctly unbiased—online news organization DNAinfo. On the other hand, he and youngest son Todd are like the minor father-son version of the Koch Brothers—the billionaire energy barons using their fortunes to turn elections for far-right Republicans. Todd, for one, has called the Kochs “great heroes who stood up and wanted to make a difference.”

Joe and Todd’s fingerprints have been all over several conservative super PACs that have raised and spent at least $30 million in the pro-Trump effort, according to a report from Politico, and they’re currently in the process of raising at least $45 million more in the countdown to Election Day. In 2013, Todd—who couldn’t hack it as a Wrigley Field maintenance man in an episode of CBS’s Undercover Boss—became CEO of Ending Spending, a super PAC professing to be against wasteful government spending. But the name is rather ironic if you consider that the Ricketts asked for $200 million in public funds for new team offices and other proposed construction on Clark Street, as well as a massive federal subsidy to pay for a renovation of Wrigley Field. Joe’s anti-Obama super PAC Character Matters became notorious during the 2012 presidential election after the New York Times reported about a leaked proposal to the organization titled “The Defeat of Barack Hussein Obama: the Ricketts Plan to End His Spending for Good.” The plan, put forward by a group of Republican strategists, suggested Character Matters spend $10 million on an ad campaign that would attempt to link Obama, a “metrosexual, black Abraham Lincoln,” to the controversial Chicago reverend Jeremiah Wright.

Early on in this election cycle, the Ricketts weren’t in Trump’s corner. Last year, the family donated $10,000 each to super PACs backing the presidential campaigns of Ted Cruz, Marco Rubio, Jeb Bush, Chris Christie, and Rick Perry. Todd chaired fund-raising efforts for Scott Walker’s doomed bid to become the GOP presidential nominee, while Joe and his wife, Marlene, donated $5 million to a super PAC called Unintimidated (also the name of Walker’s autobiography) that backed the Wisconsin governor, who’s perhaps best known for trying to destroy his state’s public unions. Todd organized fund-raising events to support Walker, including a barbecue held at his Wilmette home. He’d scheduled a Walker fund-raiser at Wrigley Field for October 2015, but it was canceled after the candidate dropped out of the race. Joe and Marlene, meanwhile, donated nearly $6 million to Our Principles, a #NeverTrump super PAC that, among other claims, accused the Donald of being a misogynist. It prompted an angry tweet from Trump in February that said: “I hear the Rickets family, who own the Chicago Cubs, are secretly spending $’s against me. They better be careful, they have a lot to hide!”

Despite Trump’s bluster, news emerged in September that Joe had done a 180 and would be donating $1 million towards the pro-Trump Future45 super PAC run by longtime Ricketts political strategist Brian Baker. “If you let all of the airtime of Hillary Clinton go unanswered,” Baker said, “it could be a disaster for the cause of limited government.”

With the help of Adelson, whose Las Vegas Review-Journal was recently the first major newspaper to endorse Trump, Future45 is working towards a goal of $70 million to fund TV ads attacking Clinton that they hope will help elect Trump and other GOP candidates. “I want to commend the Ricketts family on their business plan and how they rebuilt the Chicago Cubs in a few short years!” Trump reportedly yelled during a fund-raiser in the Chicago suburbs earlier this month. Todd Ricketts replied, “It’s gonna be a great year because YOU are going to win the presidency AND THE CUBS ARE GOING TO WIN THE WORLD SERIES!”

Here’s the kicker: according to Politico, the Ricketts also have a related pro-Trump fund called 45Committee, registered under a part of the tax code that allows tax-exempt groups to accept unlimited contributions without disclosing their donors’ names. The 45Committee essentially allows the rich to financially lend support to Trump while keeping their identities insulated from being polluted by a connection to the candidate.

While Joe and Todd Ricketts have become the money men backing candidates, Pete is actively carrying out the family’s conservative political agenda as governor of Nebraska. The Cubs co-owner and board member pumped $12 million of his own money into a 2006 campaign for the U.S. Senate that he lost to incumbent Democrat Ben Nelson by 28 percentage points. But Pete didn’t give up. He instead began building up for another run the old-fashioned way—by slowly buying off allies. He donated $1.2 million to 127 Republican candidates in state legislative races and political causes from 2006-2016, while also starting a conservative think tank called the Platte Institute. During his gubernatorial run in 2014, he used Wrigley Field as a fund-raising site. 

As governor, Pete’s pursued an agenda that would’ve made Ronald Reagan blush—which is likely why he’s been endorsed by former VP candidate turned Tea Party talking head Sarah Palin. He’s defended some of the nation’s most restrictive abortion laws, and in October 2015 he asked the Nebraska Department of Health and Human Services to investigate three Planned Parenthood facilities “to examine their records.” Pete also vetoed a bill that would’ve allowed the children of undocumented immigrants to get work licenses in the state. Additionally he unsuccessfully opposed a ballot issue to raise Nebraska’s hourly minimum wage from $7.25 to $9. 

If that’s not Grinch-like enough for you, Pete vetoed the Nebraska legislature’s move in 2015 to abolish the state’s death penalty. After legislators overrode the veto by a 30-19 vote, Ricketts has continued to push an effort to reinstate capital punishment. So far, he’s donated $300,000 of his own money to Nebraskans for the Death Penalty, with Joe Ricketts tossing in another $100,000. In total, that’s an amount nearly equal to the annual salary of Cubs’ star second baseman Javier Baez.

What about Tom, you ask? The Cubs chair, the CEO of Chicago investment bank Incapital, and unfortunate Ted Cruz doppelganger has mostly tried to play Switzerland when it comes to politics—at least publicly. Quietly he donated $50,000 to Pete’s gubernatorial campaign and reportedly cohosted a fund-raiser for Liz Cheney, the Republican hopeful from Wyoming, who appeared in Chicago with her dad Dick, the former vice president.

Any semblance of hope for liberal thought within the Ricketts family hinges on Laura, the first openly gay owner of a major-league sports franchise and no doubt the most uncomfortable person at the clan’s Thanksgiving dinner table. For years she’s been actively involved with LGBTQ organizations and charities in the Chicago area, and she runs a super PAC called LPAC, which supports gay rights causes and whose website says it “builds the political power of lesbians and queer women by electing candidates who champion LGBTQ rights, women’s equality, and social justice.” In July she hosted Clinton at a fund-raiser in her Wilmette home. 

But do Laura Ricketts’s efforts adequately counterbalance the ultraconservative activities of the rest of the family for progressive Cubs fans? Or does the clan’s internal conflict seem enough like a maze that it makes the few fans who might be concerned throw up their hands and move on?

Perhaps it’s simpler than that. Maybe the team’s pro-Trump ownership gets a break from public scrutiny because the desire to see the Cubs win the World Series fuzzes the math of fans’ moral calculus. The word “fan,” after all, is short for “fanatic,” defined as “a person filled with excessive and single-minded zeal, especially for an extreme religious or political cause.” That certainly describes some of those who’ve kept their faith in the Cubs. (The term also fits the extremist politics of most of the Ricketts family.) 

It’s no wonder Tom downplayed questions about the potential public backlash against the Cubs stemming from his family’s support of Trump.

“I’m not worried about that at all,” he said last month. “It’s no big deal.”

And he was right. It hasn’t been a big deal. But shouldn’t it be? How would fans feel if by November 8, the Ricketts had helped lead the Cubs to a World Series victory and Donald Trump to the White House?

To paraphrase a passage from the Gospel of Mark: What does it profit a man to gain a World Series championship and forfeit his own soul? 

Correction: This article has been amended to correctly identify Tom Ricketts as the CEO of Chicago investment bank Incapital.