Replacement-Level Billionaires

How the Ricketts family values made the Chicago Cubs into unlovable losers

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Major League Baseball’s hothouse economy is not any more logical or predictable than the broader one from which it is carved out by a federal antitrust exemption, but then, any marketplace that includes the New York Mets is by definition not a rational one. Baseball’s not-quite-free market tends to reflect the minor-key depravities and general cynicism and self-dealing of American capitalism circa now, if only because the same finance lordlings and legacy swells sit atop both, but it has quirks and perversities of its own. It also has norms and rules of its own, such that within the peculiar framework of baseball economics, it’s safe to say that contending teams like the Chicago Cubs generally do not get outbid on free agents like Eric Sogard.

This is no knock on Sogard, a perfectly solid and admirably versatile big league player who survived and then transcended an early-career brush with memehood—he was, because of his Graduate Student Who Sometimes Works Out appearance rather than despite it, nearly chosen by fans as Face of the MLB in a 2014 Twitter poll run by the league. Sogard was with the Oakland Athletics then. In the years since, he has moved around the league and around the diamond, adding unsexy but demonstrable value playing wherever he was needed. He’s good at what he does, but he’ll also turn thirty-four early next season and stands little chance of suddenly emerging in his mid-thirties as a bearded and bespectacled version of José Altuve. When he became a free agent in 2019, he did so as the sort of player who could reasonably expect a payday in the low millions for a job as a part-time option on a good team, or a starter on a less good one.

That combination of objective baseballing cromulence and reasonable price tag made Sogard a backhandedly valuable commodity in a sport that has, in recent years, steered into a sort of slow-rolled capital strike. Major League Baseball’s collective bargaining agreement expires in December of 2021, and the league’s richest and most powerful owners have spent the last few sluggish, peevy off-seasons demonstrating just how willing they are not to pay for the sort of stars who have historically commanded nine-figure paydays as free agents. Players like Sogard, who should represent a sort of middle class, are getting squeezed as well; absent functional dynamic market pressure from above or below, they’ve been left with smaller, shorter contracts than in years past.

In a way that smells and looks like but isn’t quite actionably collusion, MLB’s owners have decided to treat the sport’s luxury tax—a long-sought concession that owners gradually extracted from what had become a fairly complacent players’ union during the more than two decades of increasingly attrition-intensive labor peace—as a sort of salary cap. Every team is free to pay as much above the threshold as they deem fit, and while penalties escalate for teams that exceed it in multiple years, the baseline tax hit is almost laughably mild. When the Red Sox went over during their World Series–winning season in 2018, the penalty they were assessed amounted to something like the cost of a back-end starting pitcher, or roughly 2.75 Sogards. Still, since 2003, when the current system came into effect, only eight teams have ever paid the tax; last year, the Cubs were one of three teams willing to spend above the threshold, and they have made it clear that they will not do it again. There will almost certainly be a work stoppage around the negotiation of the next collective-bargaining agreement, but baseball’s owners have spent the last few years—a period of record profits and universal spikes in franchise valuations—acting as if the changes they’ll seek in 2021 are already in place.

Sogard Your Wallet

Baseball’s new and selective austerity, which the Cubs have lately come to embody, isn’t about economics. It’s about principle, if that’s the right word for rich people deciding, separately but in suspiciously perfect harmony, that they were going to see how little they could get away with paying their players. And that was how the Chicago Cubs, the team that won their first World Series in 108 years six days before Donald Trump was elected president, came to be outbid by the Milwaukee Brewers for the services of Eric Sogard in December of 2019. “Cubs just can’t add $$ until they subtract,” ESPN’s Jesse Rogers tweeted by way of explanation after Sogard signed on with Milwaukee.

Baseball’s new austerity is about principle, if that’s the right word for rich people deciding, separately but in suspiciously perfect harmony, that they were going to see how little they could get away with paying their players.

It should go without saying that the family that owns the Cubs absolutely can afford to give Eric Sogard the $4.5 million that the Brewers wound up paying him. J. Joe Ricketts, the seventy-eight-year-old founder of TD Ameritrade and the source of the money behind his family’s purchase of the team for $845 million in 2009, is worth an estimated $2.6 billion. The Cubs themselves were worth an estimated $3.1 billion in 2019, a figure that increased by seven percent over the previous year alone, and the team has had an operating income of at least $50 million in each of the five years preceding that season. Their $87 million income for the 2018 season, which followed an off-season in which the team effectively stood pat, was the third highest in the league.

And yet, three years after winning the World Series, with a roster stacked with young talent who are still mostly underpaid in precisely the ways that the sport’s collective bargaining agreement intended, the Cubs have done little besides publicly toying with the idea of trading one or more of their less-underpaid rising stars. “For the second offseason in a row, the Cubs are unable to aggressively improve a club that has clear flaws but high potential,” The Athletic’s Sahadev Sharma wrote in December of last year. “It just doesn’t seem like the way a team like the Cubs should be operating.” As I drafted this piece, the Cubs signed less-accomplished infielders Hernán Pérez and Carlos Asuaje to minor league contracts, and they were reportedly working hard to trade star third baseman Kris Bryant, whose labor grievance against the club—for manipulating his MLB service time in hopes of suppressing his salary for an additional season—was resolved in favor of the owners at the end of January. Just a matter of weeks before spring training began, the Cubs were one of two MLB teams not to have signed a free agent to a big league contract; they finally signed the veteran reliever Jeremy Jeffress to a one-year, $850,000 deal on January 28.

Helping the most luridly accursed franchise in American professional sports win a World Series after more than a century of failure would surely seem to be the sort of thing that would win the Ricketts family a pass from fans for . . . well, forever actually seems reasonable enough. And yet the goodwill that the Rickettses bought along with that long-sought title couldn’t even outlast the first term of the mincing, grudgeful aspiring monarch that they worked so hard to elect president. To a family as steeped in and blithely reverent of free-market truisms as the Ricketts family is, this can only scan as a compliment, but they earned it.

The family canceled their regular question-and-answer session at the Cubs’ annual fan convention each of the last two winters—team president Tom Ricketts made his usual address this year, and was booed—rather than face heat from fans about any of the more questionable aspects of the family’s stewardship of the team, from its hard right turn into austerity to its terraforming of Wrigleyville into a denuded burbscape to the goonishly bigoted emails sent by the Ricketts paterfamilias. “We just thought we are boring people,” Tom Ricketts claimed in 2019. Fans still turn out to see the Cubs despite the team setting the highest ticket prices in the sport, but the Rickettses have been souring the vibe in the way only they can for years now. “I wish we could talk just about baseball,” Rick Morrissey wrote in the Chicago Sun-Times last June. “But the Ricketts family keeps making that harder and harder to do. And they don’t seem to care.”

In their drab avarice and relentlessly petty competitiveness, the Rickettses are a perfect stand-in for their class at the start of a dumb new decade. They are wildly wealthy and ravenously self-interested and daily enriched further by a broken politics that serves them and their plutocratic peers lavishly and everyone else not at all. Formerly off-the-rack business-brained libertarians who spent millions on a PAC opposing Trump during the GOP primaries, they are now eager and ardent advocates of his cable-addled authoritarianism. Their wealth and newfound friendliness with the Trump administration has made them hugely powerful, but they are to all appearances glum and paranoid about this. The family’s passion for politics and influence mostly resolves to a common determination not to share what they have with anyone else. It should have been impossible for the family who turned baseball’s archetypal “lovable losers” into world champions to wind up so roundly loathed even by that team’s most ardent fans. But the Ricketts family did it by just being themselves.

Unlovable Winners

The Ricketts operation came to own the Cubs in the same way that every recent MLB owner has: through vast private wealth leveraging an equally imposing amount of debt—$450 million in this case. A massive cache of emails from Joe Ricketts’s inbox, published last year at the since-shuttered news site Splinter and my effectively defunct former employer Deadspin, reveals pretty much all the tacky rich person shit you’d expect from a nine-figure transaction between one of America’s wealthiest families and the Tribune Company, then in the process of being looted by private equity lout Sam Zell. There was a frenzy of elaborate and expensive tax-dodging legerdemain on all sides, a symphonic interplay of shell companies and shifted debt, one strategic filing for bankruptcy, innumerable consultants, and multiple instances of boardroom brinksmanship that nearly derailed the deal: sordid details that never rise to the point of becoming interesting.

The family’s correspondence around the sale reflects a peculiar but unmistakable inability to see the purchase of an iconic and beloved American institution as anything but an unusually large business deal. The closest thing to excitement in the emails is Joe Ricketts telling Tom, who has had some copies of the closing documents from the sale bound in leather “as a deal momento,” that he would be kicking in $650 for his six volumes, which he’ll put “on a shelf in the Cabana room, now the Cubs room.” There’s an anhedonic pissiness to the correspondence that’s almost but not quite poignant. The emails reveal a clan that strictly and a little sadly runs itself like a corporation, complete with board meetings, codes of conduct, spendy outside consultants, the Myers-Briggs personality test, and relentless jockeying for pride of place among the most powerful players—all of whom are related by blood and a shared business interest in the family’s massive financial trust, and united in their tremulous deference to their father.

The elder Ricketts, for his part, comes off not as a tyrant but as a familiar kind of incurious, conservative bore. He’s a standard-issue septuagenarian Fox News casualty, prone to forwarding along salty emails about Barack Obama to people who might not want to receive them and announcing that “Muslims are naturally my (our) enemy”—albeit one with the resources and spare time to add, in the same email, that he’d been “giving some consideration to having a book written with the title ‘Islam, Religion or Cult.’” Because of his massive personal fortune and pliant willingness to donate to any political cause so long as it does not advance the interests of disadvantaged or minority populations, Joe Ricketts has become a player in American politics. And yet there’s no sense in his private correspondence that he takes that power and responsibility especially seriously, or even finds it particularly interesting. It is easy to imagine him drifting from a set of mostly unexamined pro-business beliefs into the more fragrant and overtly reactionary suckholes of contemporary Trumpism simply because he started watching more television.

The Ricketts family’s internal splits are evident in the way they spend their money. Daughter Laura is a major Democratic fundraiser, a big wheel at Lambda Legal, and was a Hillary Clinton superdelegate. Son Todd is currently the finance chairman of the Republican National Committee. Pete Ricketts set a Nebraska state record for private spending in a statewide campaign that he lost by nearly twenty-eight points, but when he later managed to get himself elected governor, he spent $200,000 of his own money (Joe kicked in another $100,000) promoting a 2015 referendum that overturned a state law, which had passed over Ricketts’s veto, abolishing the death penalty. Tom retains the title of Chairman of the Chicago Cubs and thus is currently taking applications for an opening at the Cubs’ second base. However different their individual pursuits, the Ricketts progeny are united in their reflexive tendency to appeal to their father whenever they feel that some sibling or other is appearing on television too much, or getting too much credit for something. For a family with nothing much to worry about, they sure do seem to get upset a lot.

It should have been impossible for the family who turned baseball’s archetypal “lovable losers” into world champions to wind up so roundly loathed even by that team’s most ardent fans. But the Ricketts family did it.

Their squabbles read oddly like a version of HBO’s Succession edited for the low-intensity, low-stakes norms of the Hallmark Channel. While the Rickettses have mostly behaved more or less like other ultra-wealthy American families—a little bit of charity and a notably larger amount of politicized self-interest, a weakness for baubles and feuds and an abiding passion for tax-avoidance—their disputes have always seemed somehow overdetermined. In the leaked emails, the grown children frequently appeal to dad about various touch fouls absorbed as part of the unceasing family jostle. “My kids live in the same neighborhood and go to the same school as Tom’s kids,” Todd whined in an email to his father and his future-governor brother Pete back in 2009, after his brother Tom received what he considered undue media attention as the public face of the Cubs’ new ownership, “and I don’t want them to have to constantly explaining [sic] that there are equal owners when they are told that their uncle owns the Cubs.” Though reliably irritable and affronted, the Rickettses mostly just seem bored.

Dude Wrote a Book

All of this is easy to ridicule but somehow too broad to work as satire. The family’s initial foray into conservative politics, in 2010, was something called the Ending Spending Action Fund. Joe Ricketts’s preposterously smug 2019 autobiography was entitled The Harder You Work, The Luckier You Get: An Entrepreneur’s Memoir. When he abruptly and peevishly shut down two local news websites that he somewhat implausibly owned, DNAinfo and Gothamist, after they voted to unionize against his wishes, he initially removed years of articles from the websites, replacing them with a smarmy note about the business of media bearing his signature. The conservative media apparatus has become infinitely more goonish and servile around the Ricketts family, which serves to disguise their more obvious blunders. The mysteriously funded and reliably psychedelic news organ The Federalist, for example, deemed Ricketts’s book “as inspiring as it is instructive.”

For all the repellent particulars of their commitments, there’s something about the Ricketts family that reads as corny and rote. They are, to borrow a baseball analytics term, Replacement-Level plutocrats. In baseball, a “replacement level” player refers to the sort of freely available talent that could be pulled up out of the minors and slotted into a big league lineup; the Wins-Above-Replacement-Player metric reflects how much better (or worse) a given player is than that floor. At his best, Eric Sogard is a couple of wins better than a replacement player, which makes him about an average big league regular. Kris Bryant, when he’s healthy, is roughly twice as good as that. By contrast, the Ricketts family would sit right around replacement level in any yacht club or fundraising committee for a right-to-work lobbying effort—they do everything that a brood of mediocre dynasts would do, nothing more, nothing less.

To be clear, this still leaves them plenty of room for cheesy venality. It does the family a great favor to leave aside their politics, but let’s go back to the Cubs. This storied franchise saw a generation of young baseball fans grow up watching afternoon games in the summer on WGN, back when television was free. Now the Cubs organization is about to launch the Marquee Sports Network in collaboration with the right-wing television colossus Sinclair Broadcast Group, a venture that promises to deliver billions in revenues to ownership while simultaneously setting up a showdown with local cable providers. In this case, Marquee has yet to reach an agreement with Comcast, the cable provider for 1.5 million subscribers in greater Chicago. When teams like the Dodgers and Yankees launched their own networks, they managed to secure the proverbial bag while picking fights with cable carriers that made it impossible for millions of local fans to watch their teams’ games on TV. When Ricketts talked up the new network at the team’s fan convention during the winter, he was met by a wild torrent of boos. “Believe me,” he told the crowd, “you won’t be booing in a year.” (“Not sure I was booed,” he said on local sports radio the next day.)

There’s no reason to think that Cubs ownership will be any less inclined to take the money and run, fans be damned. It’s what every other member of their caste has done, after all, and they have never cleared that low and greasy bar. These are the Ricketts family values—they have never questioned, never wavered, never considered the possibility that anything on earth could matter more than their own prominence, pride, and privilege. They seem no happier for it, but they’re certainly no poorer, either. Call it a wash.

David Roth is a writer from New Jersey who lives in New York. He is on Twitter at @david_j_roth.

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