Matchmaker Leonard Leo Helps Unite Billionaires With Supreme Court Justices

Matchmaker Leonard Leo Helps Unite Billionaires With Supreme Court Justices

Matchmaker Leonard Leo Helps Unite Billionaires With Supreme Court Justices

High-court corruption is built on a network of plutocratic coziness.


Although he sits on the highest court in the land, Samuel Alito is an injudicious justice, famously given to penning ill-tempered decisions and cranky obiter dicta that offer ample evidence of a festering mind cankered with culture-war grievances. On Tuesday, Alito’s legendary cussedness became self-destructive, when he took the bizarre step of offering free advertising for a forthcoming article questioning his ethics.

ProPublica, the nonprofit journalism outlet that has previously documented Supreme Court Clarence Thomas’s cozy and undisclosed relationship with billionaire Harlan Crow, had been preparing a similar exposé on Alito’s ties to billionaire Paul Singer. In the course of researching the article, ProPublica writers sent queries to Alito. Rather than responding directly, he took the untoward step of publishing, in The Wall Street Journal, a response to an article that hadn’t yet been released.

The ProPublica article revealed that in 2008 Singer “flew Alito to Alaska on a private jet. If the justice chartered the plane himself, the cost could have exceeded $100,000 one way.” Alito never disclosed this bounty, though he was required to by federal law. The lack of disclosure in and of itself would be a scandal—even if Singer had never done business in the court. However, according to ProPublica:

In the years that followed [the trip to Alaska], Singer’s hedge fund came before the court at least 10 times in cases where his role was often covered by the legal press and mainstream media. In 2014, the court agreed to resolve a key issue in a decade-long battle between Singer’s hedge fund and the nation of Argentina. Alito did not recuse himself from the case and voted with the 7-1 majority in Singer’s favor. The hedge fund was ultimately paid $2.4 billion.

Alito’s preemptive response was the risible claim that the trip on the private jet was no big deal because all Alito did was take “a seat that, as far as I am aware, would have otherwise been vacant.” (It’s not clear why Alito thinks a seat on a private plane has no value if it would otherwise be empty, since it would in any case have been a gifted seat.) Contesting ProPublica’s depiction of a lavish vacation, Alito claims that the lodge he stayed at was “modest” and the meals were “homestyle fare.”

Alito denied that he was under any obligation to declare the trip. He further insisted that Singer wasn’t listed as a party in the cases brought before the court (most of which weren’t taken up). This includes the one court case that was taken up, the $2.4 billion settlement in Republic of Argentina v. NML Capital, Ltd. Alito’s claim of ignorance regarding this last case strains credulity, since Singer’s dispute with the government of Argentina, which included an attempt in 2012 to seize Argentine ships in Ghana, was widely reported. We are apparently expected to believe that Alito knew Paul Singer socially and vacationed with him—but never noticed any of the numerous newspaper articles about the billionaire.

Alito’s suspect relationship with Singer is only one data point in a larger scandal. The problem isn’t just a single friendship but the entire network of plutocratic coziness that has been set up to make right-wing justices feel secure in constantly deciding in favor of the rich. In 2005, the late Justice Antonin Scalia went on a similar fishing trip with Singer. When Scalia died of a heart attack in 2016, it was at a luxury West Texas ranch where he was also staying for free. This is further proof that living off the beneficence of the ultra-wealthy had become normal for Scalia. Clarence Thomas has repeatedly gone on angling trips in the Adirondacks with Harlan Crow. There’s something fishy going on here—and it’s not just whatever luscious Alaskan salmon Alito and Scalia might have reeled in.

You might well wonder: Just how do all these justices keep finding billionaire buddies? The answer is, they have a matchmaker, someone who makes it his job to keep right-wing judges, donors, and political actors in alignment: Leonard Leo. Leo is currently cochair of the board of directors of the Federalist Society. Over the last few decades, he’s built the society into the headquarters of the legal right, the place where lawyers are groomed into ideological conformity, judicial nominees are forwarded to the Republican Party, and billionaire donors are kept apprised of their investments. Summing up ProPublica’s reporting, New York Times columnist Jamelle Bouie observed, “The big takeaway from these articles to me is that Leonard Leo is THE conduit for judicial corruption.”

Expanding on this thought, Josh Marshall, in Talking Points Memonotes:

Everyone here is part of Leo’s network. Harlan Crow is a big Republican donor but also a big Federalist Society donor. So is Paul Singer. So is the owner of the fishing lodge. In fact, Leo’s network is so vast and deep-pocketed that eventually he decided he was too big for the Federalist Society and struck out on his own. Indeed last year he secured a record-breaking $1.6 billion donation as a kind of judicial corrupt grubstake to fund all his future endeavors.

One could add that we still don’t know the full extent of Leo’s network, which could well include other justices. According to Mother Jones, the once-burning question of who paid off Brett Kavanaugh’s massive debts has in fact been solved: It turns out he was subsidized by his wealthy parents, who allowed him to live a lavish country-club lifestyle on a government salary. But now that Kavanaugh is on the court, who is to say that Leo hasn’t also connected the justice, who has a record of wanting to live a lifestyle well beyond his tax bracket, to a billionaire benefactor? For that matter, might Justices Neil Gorsuch, Amy Coney Barrett, and John Roberts also have hidden pals who shower them with worldly goods? Only Leonard Leo knows for sure.

Marshall argues that “it’s probably wrong to see this too much in transactional terms. Certainly, all of these lavish gifts should be reported and the justices should recuse themselves when cases arise dealing with their ‘close friends.’ But the larger issue is the way the justices remain ‘kept’ in perpetuity by the right-wing activist donor network that placed them on the Court in the first place.”

This right-wing support network also gives the justices good reason to remain on the courts—at least until there is Republican control of the presidency and Senate. After all, a septuagenarian Supreme Court justice might think that they were better off retiring and taking the inevitable lucrative private-sector job that awaits them. As Clarence Thomas said in 2001, “The job [of sitting on the Supreme Court] is not worth doing for what they pay,” But with friends like Harlan Crow, a Clarence Thomas can stay on the court as long as he likes while still enjoying a lifestyle comparable to that of a partner in a top-tier law firm.

Leonard Leo’s response to the ProPublica article is worth quoting at length:

Justices Alito and Scalia…are among the most intelligent, strong-willed and independent legal minds I have ever known, and they can be what they are without outside influence because they serve for life. No event, meeting, dinner, or trip would influence their approach to the rule of law.

We all should wonder whether this recent rash of ProPublica stories questioning the integrity of only conservative Supreme Court Justices is bait for reeling in more dark money from woke billionaires who want to damage this Supreme Court and remake it into one that will disregard the law by rubber stamping their disordered and highly unpopular cultural preferences.

This might seem like a contradictory statement, since on the one hand Leo (who is a massive conduit of right-wing dark money) is suggesting that there is no need to worry that right-wing billionaires who are free with their money can influence judges, while on the other he is also warning of “dark money from woke billionaires.” If “dark money” is bad when it comes from “woke billionaires,” why isn’t it bad from reactionary billionaires?

The curious word “disordered” offers a hint. Leo is a conservative Catholic, and “disordered” is often used in his circle as a euphemism for LGBTQ people (whom Pope Benedict XVI notoriously described as “objectively disordered”). Leo’s coded message here is that money is bad only if comes from people who want to promote tolerance for LGBTQ people. That’s a sin without forgiveness. Money from good, normal, healthy billionaires, the type who like to go fishing with the boys in the wild, is inherently virtuous. Such is the moral vision that allows Leo to justify his well-ordered corruption.

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