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Better Hate An Owner

The Ricketts Kids Don’t Know How To Care For Their Toys

Illustration by Jim Cooke

Welcome to Better Hate An Owner, a recurring feature in which we learn more about all those awful old people who get to hold the trophy first at championship ceremonies. Today’s entry is about the Ricketts family.

How much of their soul did they lose in making their money?

Not a lot, I suppose, because it’s hard for money you didn’t actually earn to make any mark on your soul. The Ricketts kids’ wealth is entirely owed to their father, Joe, who founded TD Ameritrade and became obscenely rich when his children were still very young.

Are they fail-children?

Absolutely. Scan any of the siblings’ bios and you’ll come away with the image of a kid whose life and career has unfolded in the comfort and cover of their father’s wealth and influence. Laura came the closest to striking out on her own, earning a law degree and then becoming a prominent D.C. hack in the Democratic Party, even serving as a superdelegate at the 2016 DNC. Tom, Todd, and Pete followed the same general career path as so many useless rich kids in America: graduated from business school, farted around various inconsequential jobs at various financial institutions with awful names like “Experian Capital,” and ultimately returned home to claim a cushy position in the family business. Todd and Pete eventually leveraged their father’s money and political connections into political careers—Todd has been the chairman of the Republican National Convention since 2018, and Pete managed to get himself elected governor of Nebraska.

How much public financing have they sucked out of the community?

Not as much as they would have liked. When the Ricketts family purchased the Cubs in 2009, they did so with the intention of renovating not only Wrigley Field, but the entire neighborhood around it. Thanks to a cache of emails from Joe Ricketts’s inbox that were uncovered by Splinter in 2018, we know Todd was furious about the Chicago political establishment’s refusal to subsidize the Wrigleyville renovation with public funds. In an email to Tom and Joe, Todd wrote that the family should “contemplate moving” the team due to then-Mayor Rahm Emanuel’s refusal to offer up public funds.

“It hurts my feelings to see Tom treated this way,” replied Joe. “He is way superior to the Mayor in every way.”

The Ricketts clan eventually had to go forward with their renovations without any public subsidies. The work was originally projected to cost $500 million, but Tom recently claimed that the budget was overrun by 100 percent. The family did recently manage to register Wrigley Field as an official historical landmark, which could get them a 20-percent income tax credit on their renovation costs.

The Epstein Degree: How many degrees removed from Jeffrey Epstein are they?

There are almost too many vectors to choose from. We’ll go with the most direct: Laura has been a fixture in the Clinton political machine for years, and hosted Hillary Clinton at her home for a fundraiser in 2016. Former Clinton confidant Doug Band just recently claimed that Bill Clinton did in fact travel to Epstein’s private island in 2003, and that Chelsea Clinton was friends with Ghislaine Maxwell, who was invited to Chelsea’s wedding in 2010.

What are their political affiliations?

Depends which kid you’re talking about. Laura has always been a partisan Democrat firmly entrenched in the Clinton-Obama wing of the party. Todd and Joe were once staunch anti-Trump conservatives, donating over $5 million to an anti-Trump PAC during the 2016 Republican primary. They reversed course quickly once Trump secured the nomination, though, and poured $1 million into a Trump-friendly PAC. Todd wasted no time further ingratiating himself with Trump, and became Trump’s nominee for Deputy Commerce Secretary in November 2016.

Pete initially got into politics as the kind of charmless, Jeb Bush-style scion who populates statehouses and congressional seats throughout the country. He’s just as much of an opportunist as his brothers and father, though, and has recently burrowed deeper into rancid, reactionary politics as the appetite for such derangement has grown in his party and the country overall. His latest gambit as governor of Nebraska was threatening to withhold $100 million in COVID-19 relief money from local governments if they continued to require people to wear a mask while entering government buildings. He followed that up by arguing that immigrants without legal status shouldn’t be given the COVID-19 vaccine before any legal residents.

How an influential family of rich freaks chooses to present itself politically and the directions in which it is inclined to throw around its money can only tell you so much about what they really think about the world, though. Political donations and policy agendas can tell you what people like this are willing to do to in order to protect their gilded status, but it’s much more difficult to get a sense for what an oligarch really believes. In the case of Joe Ricketts, we can just look at some of the leaked emails from Joe’s inbox that Splinter reported on in 2019. “Therefore we cannot ever let Islam become a large part of our society,” he wrote in one message. “Muslims are naturally my (our) enemy due to their deep antagonism and bias against non-Muslims.”


The thing you really need to understand about the Ricketts kids is that they are just that: old and unhappy kids, little rich babies who are of no use to anyone.

In 2019 I sorted through thousands of pages of emails and documents from Joe’s inbox in order to write a story about how the family came to acquire the Chicago Cubs for just under $1 billion. Those documents revealed a lot about how the family operates, but two things stuck out to me: 1) Tom, Todd, Laura, and Pete own the Chicago Cubs in the same way a schoolchild “owns” a lollipop that their daddy bought them, and 2) the siblings are absolutely as petty and vain as you probably imagined they would be.

On the first point, it should be made clear that the Ricketts kids did not purchase the Cubs with any of their own money. $450 million of the $845 million purchase price was met through debt financing, and the rest was paid for through the liquidation of various trust funds that Joe had established for his children with his TD Ameritrade fortune. The Cubs are quite literally an expensive gift that Joe purchased for his children, and even though the family has gone to great lengths to explain that Joe is not the team’s principal owner and is not involved in the day-to-day operations of the team, there’s no getting around the fact that his wealth and influence made the purchase possible. Joe’s email inbox revealed that he was kept very much in the loop throughout the negotiating process leading up to the sale, and he continued to receive regular updates about the Cubs’ financial situation well after his children took over stewardship of the team.

As for the pettiness and vanity, the emails in Joe’s inbox revealed that his kids were regularly at odds over who was and wasn’t receiving media attention over the family’s pursuit of the Cubs. Laura sent multiple emails to the family complaining that Tom, the current chairman of the Cubs and the public face of the ownership group, was getting too much credit for spearheading the negotiations. “OMG. Just saw Tribune front page at the Newseum in DC. The heading is ‘Meet the Cubs’ $900 Million Man’ with a big photo of Tom next to it. Which is disappointing,” wrote Laura in one email. “Also, I think this media issue is actually part of a bigger issue that deals more with our family dynamic,” she whined in another.

Todd did plenty of kvetching of his own, at one point writing, “…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 explaining that there are equal owners when they are told that their uncle owns the Cubs.” When describing how Tom reacted to this complaint on a phone call, Todd wrote, “I have to say, I was shocked and disappointed with aggressive, hostile tone in which Tom responded. In fact, I would call it an ‘uninvitation’ to be part of this process.”

Having their team handed over to a family spoiled brats wasn’t immediately bad news for Cubs fans, though. Yes, Tom and his siblings went about turning Wrigley Field and the surrounding neighborhood into a charmless, Disneyfied version of what it used to be, but they also started things off by spending money to improve the team. They brought in Theo Epstein to run the baseball operations, signed and developed a whole bunch of good players, and in 2016 delivered the city of Chicago the first Cubs championship in 108 years.

In many ways, the Ricketts fit the profile of a sports fan’s ideal ownership group. The worst owners in sports are the misers who treat their teams like a business, always more concerned with their P&L sheet than with putting an entertaining, competitive team on the field. The best owners are the ones who treat their teams as exuberant vanity projects, and care more about the thrill of winning and public adulation than they do about financial responsibility. The Ricketts, a group of siblings who received a team as a gift from their father and whose correspondence shows were clearly highly invested in receiving positive press, had every reason to conduct themselves as members of the latter. For a time they did, and it got them a championship.

But things have changed since the siblings gathered on the field to pose with the World Series trophy in 2016. The Cubs looked like they were on the cusp of establishing a dynasty after winning the title, went on to underachieve, and are now embarking on a totally unnecessary and cynical rebuilding phase. Once so concerned about the glory that would come from owning the Cubs and who would get to share in it, the siblings now seem more concerned with playacting as Serious Business Kids who have to make sober decisions in order to secure financial stability for the priceless baseball team. Who needs a second World Series trophy when you can instead put together a healthy financial report to show to daddy?

Almost as soon as the Cubs’ championship rings were handed out, Tom started making noises about the team’s payroll being bloated. For the last few years it seems like it has been impossible for him to speak in public without mentioning how heavily the team’s finances were weighing on him, and he eventually admitted that he was treating MLB’s luxury tax threshold as a de facto salary cap. Things got so bad that Tom was booed at a January 2020 fan festival. It shouldn’t be possible for anyone to squander the goodwill that comes from ending a 108-year title drought, but the Ricketts managed to do so in just four years. And those boos rained down before Theo Epstein left the team, before Yu Darvish and Kyle Schwarber were offloaded in salary dumps, and before reports about Kris Bryant and Willson Contreras getting traded started to intensify.

The Ricketts’ dad handed them one of the most prestigious sports franchises in the world, and it seems to have taken them just about a decade to lose interest in it, or at least to make it just another joyless prize in their endless and bottomlessly petty intra-family squabbles. They got their renovated ballpark, their little real estate fiefdom, their championship banner, and all the fawning press coverage that came with delivering the Cubs to the mountaintop. But what comes after all that, when the glow has faded and it’s time to get on with the work of owning a baseball team? The Ricketts are answering that question by peevishly cutting costs and beginning to treat their plaything—which, again, is an American institution beloved by millions of people—like an actual business. This makes them the worst kind of silver spooners: the kids who get a shiny new toy from dad whenever they want, and then decide they only really want to play with it once.