Sleazebag? Karma Comes Knocking for Leonard Leo
For Trump, it doesn’t matter how loyal or subservient anyone has been in the past.
Trump’s flip-flop
As someone who has spent much of the past seven years trying to make sure that more and more Americans understand the singular and, in my view, completely inappropriate role Leonard Leo has played in the capture of the U.S. Supreme Court and other judicial offices, I never expected Donald Trump to be my unwitting ally. But, wow, did Trump light up Leo’s name late last week. Trump posted this statement:
It was suggested that I use The Federalist Society as a recommending source on Judges.… [But I] then realized that they were under the thumb of a real ‘sleazebag’ named Leonard Leo, a bad person who, in his own way, probably hates America, and obviously has his own separate ambitions. He openly brags how he controls Judges, and even Justices of the United States Supreme Court—I hope that is not so, and don’t believe it is! In any event, Leo left The Federalist Society to do his own ‘thing.’
Who exactly is Leonard Leo?
Almost a decade ago, candidate Trump announced that he had outsourced the selection of potential Supreme Court nominees to Leonard Leo. That announcement came as the Republican Party refused to confirm Barack Obama’s nominee to fill the vacancy caused by Justice Antonin Scalia’s sudden death during a secretly gifted luxury vacation in February 2016.
By September 2018, Neil Gorsuch was confirmed. And on the eve of the Senate Judiciary Committee’s hearings on Brett Kavanaugh’s nomination to the Supreme Court, in video from a circuit court Federalist Society event that I flagged for numerous reporters, Justice Clarence Thomas joked that Leo was “the third most powerful man in the world.”
Leo took a victory lap after pushing Kavanaugh onto the bench despite the credible testimony against the nominee–just as Leo helped Thomas win his seat, despite credible testimony against him. Kavanaugh clearly ripped a page from Thomas’s playbook in hotly denying the calm and compelling personal account of Dr. Christine Blasey Ford.
(Full disclosure: I personally wrote some of the internal memos Republicans took from a Senate server and were given to Kavanaugh when he was working in George W. Bush’s White House Counsel’s Office, though he denied he received the memos–before the evidence was released during his Supreme Court nomination. For this reason and others, I fought against Kavanaugh’s confirmation, urging that he should be impeached rather than confirmed for lying repeatedly to the Senate.)
A little bit easy, a little bit sleazy … or a lot?
Meanwhile, the great investigative team of Robert O’Harrow and Shawn Boburg at the Washington Post uncloaked the massive amount of money flowing through groups tied to Leo, clocking more than $250 million to block Obama’s nominee and confirm Gorsuch, a tally that did not include the amounts that would later be uncovered around the Kavanaugh nomination to the Supreme Court.
When Evan Vorpahl and I updated that figure through 2020, it totaled more than $600 million, and that was before the public learned that a right-wing Chicago billionaire who was aligned with Kansas billionaire Charles Koch had given Leo control of a $1.6 billion trust fund in 2020. (O’Harrow, who later became a dear friend of mine, passed away suddenly last year, a huge loss for our world. He was in the midst of writing a beautiful book about the cataclysmic loss of the mayfly.)
Back in 2019, when O’Harrow and Boburg broke their blockbuster story, they also discovered that while Kavanaugh’s nomination was pending, Leo had paid off his home mortgage over 20 years ahead of schedule. Then, on the eve of Kavanaugh’s confirmation to the Supreme Court, Leo closed on a $3 million Robber Baron era mansion in Maine, with a $1 million down payment. You see, Leo was a volunteer in aiding Trump with his Supreme Court picks and so did not have to fill out the kind of financial disclosure forms about income sources that a White House employee would have to complete.
Just a few months after O’Harrow and Boburg reported on Leo’s mansion in Maine, Leo paid off that $2 million+ mortgage. Then he held a fundraiser for Maine’s U.S. Senator Susan Collins at his mansion. Leo’s soiree for her came almost a year after she provided the pivotal vote to get Kavanaugh confirmed to the highest court in the land, despite the serious allegations against him and very real concerns that he would help overrule Roe v. Wade, which he then did in 2022 in the Dobbs edict.
Back in 2019, when the Washington Post’s documentary team–led by Dalton Bennett–asked Leo about the non-profit and for-profit groups Leo was tied to as part of his court capture plans, Leo seemingly flinched and then looked into the camera to say he doesn’t talk about money because he’s an ideas man. Yeah, right. He was raising millions of dollars from secret sources to change the idea of our rights to suit his will and the will of the billionaires backing him. And Leo’s ties to billionaires to accomplish his agenda didn’t start just then.
As Boburg documented, Leo had arranged for someone to secretly underwrite Ginni Thomas’ salary back in 2011-2012 through one of the Leo-tied groups. When the excellent investigative reporter Heidi Przybyla followed up in 2023 with new details about Leo’s relationship with the Thomases, the spokesperson for Leo and the group refused to comment on whether Leo was still making secret arrangements to pay Ginni’s salary. The easiest thing in the world would have been to say it had stopped, if it had or since has stopped. And, as I documented, Leo was also tapped in 2011 by Scott Walker’s political campaign allies to secure a six-figure sum to keep the Wisconsin Supreme Court on Walker’s side as he decimated public employee union rights in that state. As ProPublica documented in its Pulitzer-prize winning series, years earlier Leo began arranging luxury travel for Supreme Court justices Thomas and Sam Alito, sometimes joining them on fabulous vacations underwritten by billionaires.
This isn’t even close to the end…
Although Trump’s rage post on Truth Social claims Leo left the Federalist Society, Leo just stopped getting paid by it: he co-chairs its board and helps fund its operations via groups backed by the billion-dollar trust fund he controls. Leo even tried to help Trump stay on the ballot in Colorado–an outcome Chief Justice John Roberts orchestrated–by trying to prevent his board co-chair Steven Calabresi, who co-founded the Federalist Society, from supporting the ruling of the Colorado Supreme Court to bounce Trump from the ballot based on the plain language of the 14th Amendment, which the Roberts Court then neutered to pave the way for Trump’s return.
But, like a serial abuser, for Trump, it doesn’t matter how loyal or subservient anyone has been in the past – just look at Nikki Haley. All that matters is 100% servility. To Trump, that means that Leo failed him by not choosing judicial nominees who would be 100% servile, 100% of the time.
What I’m reading + watching:
This is my new book, which details Leonard Leo’s regressive agenda for our rights and his ambitions to capture the U.S. Supreme Court by filling it with right-wing operatives, and I am making the final edits to the galleys before it gets printed and digitized (it’s available for advance orders here).
COURIER’s new shows: How Is This Better? From Akilah Hughes, which provides much-needed reality checks on Trump’s golden age of grift, and REPRESENT, a mini docuseries chronicling reproductive rights activist and Gen Z influencer Deja Foxx’s run for Congress
Greg Olear’s Prevail edition on “Sleazebag Wars”
Greg’s newest piece discusses Leonard Leo, along with right-wing anti-democracy extremists Elon Musk and Curtis Yarvin, and gives a well deserved shout-out to Tom Carter, who has been trying to get reporters to cover who Leo is for almost as long as I have (more to come on that front).
And, as always, the U.S. Constitution.
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