Karma comes for Leonard Leo

June 1, 2025

“End of the Day” (2016) Glass sculpture by Tacoma artist Dale Chihuly, hanging from the dome at Union Station in Tacoma which now houses the city’s federal district court complex

Maybe the angels weren’t on his side after all….

I have hoped, for some time, that more Americans would know and care more about Leonard Leo.

He and I have very little in common. We were both raised Catholic, but I have fallen away and Mr. Leo has, if anything, become more devout, at least outwardly, and with a version of devotion I don’t share. Let’s just say his wardrobe of Catholicism includes a pike and a large suit of armor that’s not a good fit for me. I’ll try to be restrained on this subject, out of respect for other devout and practicing Catholics, some of whom are siblings.

That said, what happened to Leo this past week is a tad too bizarre to cast as a Bible story. It’s actually horrifying and comically gratifying at the same time. Leviticus meets Fargo (the movie.)

Donald Trump—a man who would likely be in jail but for Leonard Leo’s success in stacking the Supreme Court—wildly tore into Leo on Thursday—denouncing him as “a real sleazebag…a bad person who, in his own way, probably hates America.”

Whitworth drama students performing in Crossing the Line, a play about police, communities and violence (2008).

This is so surreal—almost as if Kristi Noem had put a bullet in Lassie, or Rin Tin Tin, before turning her gun on the goat. The irony is that Leo’s life work—shaping the American judiciary to elevate the wealthy and the privileged, often at the expense of ordinary citizens—now finds him spurned by the person who most embodies, and benefits by, that work.

By way of background, Leonard Leo has been deeply involved in preparing and promoting ultra-conservative justices to the Supreme Court beginning with Clarence Thomas’s successive nomination in 1991. But his reach—through the conservative Federalist Society and similar private foundations extends well beyond the Supreme Court. For example, he helped funnel money to support the pro-Trump activism of Thomas’s wife Ginni and worked closely with Trump and his team to appoint more than 200 federal judges (nearly 90 percent of whom were past or current members of the Federalist Society) in Trump’s first term. Indeed, for this and his subsequent work to alter the course history through judicial appointments, Thomas once half-jokingly introduced Leo to a fawning audience as the “third most powerful person in the world.”

Photo-like painting by artist Sharif Tarabay depicting Leonard Leo (second from the left) at billionaire Harlan Crow’s Adirondack retreat. Crow is on the right side of the image, with Supreme Court Justice Clarence Thomas (holding a cigar) to his right.

One remarkable benchmark in the bizarre fracas that erupted Thursday is that Leo played a pivotal role in the elevating all six Supreme Court judges—Thomas, Samuel Alito, Neil Gorsuch, Brett Kavanaugh, Amy Coney-Barrett and Chief Justice John Roberts—who put their signatures to the historic decision in Trump v. United States last summer. This was the decision that conveyed to Trump (and future presidents) a broad shield of immunity for crimes committed in their “official acts” as president. (It will come as no surprise that Eileen Cannon—the Florida judge who granted extraordinary deference to Trump in the Mar-a-Lago classified documents case—was a longstanding member of the Federalist Society prior to her appointment by Trump.)

It begs a simple question. Who could ask for more?

Well, Trump, it turns out.

Trump’s brutal attack on the person who built the Supreme Court majority that most likely kept Trump out of jail and enabled his return to the presidency is as revealing as it is astonishing. More so than ever it demonstrates the depth of Trump’s resolve to govern as a despot.

What I hadn’t appreciated is that while Leo and Trump are both really bad for democracy, bad for humanity and bad for the planet, they are different flavors of bad.

Let’s start with Leo, the vaunted fundraiser and judge finder who Trump chose to help him pick judges for his first term. For sure, judges who opposed Roe v. Wade were going to be on that list, but so too were judges who favored gerrymandering and restricting voting rights (i.e. to disenfranchise African-American voters, who tend to vote for Democrats) and those who view money as tantamount to speech when it comes to campaign financing.

Journalist Chris Hayes explains the depth of Leo’s controversial activities below:

There’s a general rule about violence that the right to swing your fist ends where your knuckles reach my nose. The corollary for religion is that it’s okay to proselytize, and even slide your literature under doors. It’s not okay deprive someone of their voice or vote because they resist your beliefs. But this is essentially what Leo does. He actively promotes right-leaning judges who will empower the voices and aims of the powerful at the expense of the marginalized and less powerful.

What may have shocked or at least surprised Leonard Leo Thursday is that Trump views politics and justice as purely transactional—not whether laws or judgements are good for society and the democratic realm, but whether they are good for Trump. Trump’s beef is that many of the conservative judges who were on Leo’s and Federalist Society’s short list for federal judgeships have subsequently ruled against him in cases where he’s wildly overstepped his constitutional authority. His outrage is comical (ranting against judges upholding a constitution written by rebels who’d risked their lives liberating the new country from just the sort of tyrant Trump aspires to be) but also deeply disturbing to anybody who made it through fifth grade civics.

Leo and the Federalist Society are, by no means, a velvet glove operation. By and large, their method involved a long, extremely well-funded, below-the-radar campaign to systematically tilt the U.S. judicial system toward the interests of corporations, the ultra-rich, conservative Christians, and Republican populists casting civil rights and women’s rights as subversive “DEI” activism. It was and is a long range plan that is supposed to be subtle, incremental but steadily regressive.

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Trump just wants fealty. And he wants it quickly—in the full light of day, capped with a military parade with real tanks. His brutal attack on the person who built the Supreme Court majority that most likely kept Trump out of jail and enabled his return to the presidency is as revealing as it is astonishing. More so than ever it demonstrates the depth of Trump’s resolve to govern as a despot. You’re either all in for Trump and what Trump wants, or you’re a traitor, a target, and someone “who probably hates America.”

Even if you’re Leonard Leo.

—tjc