Looks Like Poisoning The Country With A Far-Right Judiciary Is Very Lucrative

The individual who has had the largest impact on the federal judiciary is probably Leonard Leo, the Federalist Society mastermind. Through his network of nonprofit advocacy group -- and more recently, a few for-profit organizations -- Leo had gotten his fingerprints all over the federal judiciary. Seriously, FedSoc has a goddamned chokehold on conservative judicial candidates. Every one of the GOP-nominated Supreme Court justices are current or former members of the organization, and the organization has been actively curating lists of judicial nominees that specifically align with a host of right-wing political goals.

Leo's been busy cultivating dark money for some time now, most recently was revealing control over $1.6 billion through the "Marble Freedom Trust." But Politico now has an investigation into the transfer of $43 million from Leo-related nonprofits into a for-profit organization led by Leo. They also track how as Leo's influence over federal judiciary appointments increased, so did his personal wealth.

As Leo became Donald Trump's "judge whisperer" in 2016, his "lifestyle took a lavish turn."

A POLITICO investigation based on dozens of financial, property and public records dating from 2000 to 2021 found that Leo's lifestyle took a lavish turn beginning in 2016, the year he was tapped as an unpaid adviser to incoming President Donald Trump on Supreme Court justices. It's the same period during which he erected a for-profit ecosystem around his longtime nonprofit empire that is shielded from taxes. Leo was executive vice president of The Federalist Society at the time.

And the timeline of Leo financial boons tracking the far-right's judicial victories is eery:

Weeks after Justice Anthony Kennedy announced his retirement, in August of 2018, Leo paid off the mortgage on his home in Virginia after making numerous renovations.

Just months after that -- and one day before the Senate took a controversial procedural vote clearing the way for [Brett] Kavanaugh's appointment to replace Kennedy -- Leo bought a second home, a $3.3 million mansion in Mount Desert, Maine.

Hmm... Maine. Why does that stick out when recalling Kavanaugh's problematic ascension onto the Court? Oh, yeah...

It was there [Leo's mansion in Mount Desert, Maine] he hosted a controversial fundraiser for Sen. Susan Collins, the Maine Republican whose vote for Kavanaugh was considered decisive. A year later, on July 3, 2019 -- and about a month after the Washington Post first revealed the 11-bedroom mansion's existence -- that mortgage too was paid in full, according to a lien discharge record. Following apparent improvements, the home was assessed for $4.4 million in 2022.

And as the ultraconservative High Court set about remaking American jurisprudence in their image, Leo was notching other indica of wealth:

Meanwhile, in 2021, the same P.O. Box used to purchase Leo's first mansion was used to buy another home about a mile away in Mount Desert for $1.65 million. This one was purchased from an heir to the financier and philanthropist Richard K. Mellon.During that same period, Leo and his wife, Sally, became "Stewards of Saint Peter," a designation given to those pledging more than $1 million to Vatican initiatives, sponsored events and made multiple additional donations ranging from $10,000 to $75,000 to Catholic charitable causes and $75,000 to a COVID relief fund in Maine.

Leo also acquired a wine locker at Morton's Steakhouse and hired the chief steward at the Trump International Hotel as his wine buyer, according to the book, "Supreme Ambition."

Remember, Leo got started remaking the federal judiciary while running nonprofits. And when those nonprofits start giving your newer for-profit organization millions of dollars, well, there may be some questions asked:

"That's a classic type of situation the IRS looks into if it appears you [via a nonprofit] are shoveling money to yourself in a for-profit context," said Philip Hackney, an expert on tax law and charities who worked in the Office of the Chief Counsel at the IRS.

He continued:

Hackney, the former IRS official, said that while there's no explicit prohibition on conflicts of interest in U.S. tax law, IRS investigations are typically triggered when an individual creates a nonprofit that then pays a for-profit that "makes them very wealthy," he said.

It certainly is interesting how much money Leo seemingly has netted for his advocacy work. Though Steven Calabresi, Leo's FedSoc co-chairman, doesn't think that's *why* he got into the biz, well, it sure don't hurt, "I personally don't believe that Leonard is motivated by greed," he said. "I think Leonard is motivated by ideology and ideas. I do think he likes to live a high-rolling lifestyle, but I don't think he's in the business because of the money."

Nice work if you can get it -- that is, if you're interested in a court system far to the right of most Americans.

Kathryn Rubino is a Senior Editor at Above the Law, host of The Jabot podcast, and co-host of Thinking Like A Lawyer. AtL tipsters are the best, so please connect with her. Feel free to email her with any tips, questions, or comments and follow her on Twitter @Kathryn1 or Mastodon