Malaka Of The Week: Leonard Leo

As our readers know all too well: I’m a film noir buff. The shadows of blinds play an important part in noir atmospherics. Sometimes, they cast a shadow on the protagonist, other times on the villain.

The man in the shadows above is Leonard Leo the corrupt creep who brought us the Gorsuch, Kavanaugh, and Barrett nominations. And that is why Leonard Leo is malaka of the week.

This is a 21st Century noir about an ideologue who couldn’t resist the temptation of dark money. According to Politico’s Heidi Pryzbala:

“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.

The for-profit and nonprofit entities share more than just Leo’s involvement: The same longtime ally managing the books for two of his new leading nonprofits, Neil Corkery, is also chief financial officer of Leo’s for-profit company, POLITICO confirmed in IRS filings. One of those nonprofits paid the for-profit $33.8 million over two years.

“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.”

Leonard Leo’s femme fatale is greed. He’s yet another person corrupted by contact with the Impeached Insult Comedian. It’s as if breathing the same air as Trump turns one into a grifter.

I suspect Leo saw this as a win-win situation: he radicalized SCOTUS and simultaneously made himself a rich man. It’s particularly nauseating given Leo’s pious public persona. He’s long claimed that his anti-abortion zealotry is based on his Opus Dei-style Catholic faith. If that was true, that changed when the Kaiser of Chaos entered the picture:

“Over the two decades before he became Trump’s “judge whisperer,” Leo had maintained a largely middle-class lifestyle directing one of Washington D.C.’s many nonprofit organizations.

Since 2016, however, his recent wealth accumulation has included two new mansions in Maine, four new cars, private school tuition for his children, hundreds of thousands of dollars in donations to Catholic causes and a wine buyer and locker at Morton’s Steakhouse, according to POLITICO’s review of public records.”

Maine? Setting for Stephen King books and home of LL Bean, Runaround Sue Collins, and Tucker Carlson. That’s fast company for a guy with the demeanor of an altar boy. Here’s my theory: once Trump became president* Leo decided to cash in his Federalist Society chips because he felt untouchable knowing the Trumpified IRS would leave him alone; call it malign neglect.

One of the key components of malakatude is hypocrisy. For decades, Leonard Leo proclaimed his rectitude while bringing the world terrible judicial nominees who share his legal philosophy. I had heard of him before the Kavanaugh mess, but that’s when he became a major player not just a high priest of the Federalist Society.

The Federalist Society was becoming a thing when I was in law school. I even attended a meeting of the Tulane Law chapter for shits and giggles. The air of pious sanctimony trumped the free food on offer. Cluelessness remains the jam of the head of that ostensibly non-profit organization:

“Steven Calabresi, Leo’s fellow co-chairman, and President Eugene Meyer have sought to “keep distance” from Leo’s activities, said Teles, including by granting leaves of absence for Leo around his advocacy work, he said. Still, the Federalist Society has become financially intertwined with Leo, receiving $5.6 million in grant money from The 85 Fund in 2020.

In an interview, Calabresi said he didn’t know anything about Leo’s work beyond the confines of the Federalist Society.

“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.”

Holy unintentional humor, Batman.

The Federalist Society have long been useful idiots for “libertarians” such as the Koch brothers and others who are obsessed with tax avoidance. That makes Leonard Leo a capitalist tool as opposed to an archbishop of “conservative” judicial ideology.

Film noir villains have been known to cloak their villainy with a principled exterior. Leonard Leo was surrounded by wealthy people living “high-rolling lifestyles” and wanted to join the party. He went from a man in the shadows to a shady character in his own right. And that is why Leonard Leo is malaka of the week.

The great rock multi-instrumentalist David Lindley died recently at the age of 78. He wrote my favorite lawyer song in which he rhymes lawyer with liar. Over the years, I’ve used it many times at First Draft. It applies to the Leonard Leo film noir as well.

The last word goes to David Lindley & El Rayo-X:




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