CNN
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President Donald Trump usually touts his conservative judicial legacy, and he possibly owes no one more than Federalist Society leader Leonard Leo for that.
But as Trump raged over a three-judge panel’s decision against his tariff plan Thursday night, he dragged Leo into his Truth Social missive. He called Leo a “real ‘sleazebag’ …. A bad person, who in his own way probably hates America.”
Trump and Leo have clashed in recent years. But their shared history of success makes Thursday night’s harsh comments especially striking.
And Trump’s remarks wildly disregarded the legacy the well-monied, deeply connected Leo helped provide him, including the vast stocking of important US appellate courts and appointment of three of the nine Supreme Court justices: Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett.
In 2016, Leo provided names of possible Supreme Court nominees that then-candidate Trump touted during his campaign. It was a novel move and one that helped Trump bolster his conservative bona-fides with the Republican base.
The one-time alliance produced some of the most outspoken conservatives on the lower courts. On the Supreme Court, all three of Trump’s picks were crucial to overturning Roe v. Wade in 2022 and providing Trump substantial immunity from criminal prosecution in 2024.
Leo’s network helped vet all the jurists that produced those opinions. The Federalist Society had served Republican presidents for years before Trump took office. Leo met with Chief Justice John Roberts and Justice Samuel Alito prior to their 2005 nominations by President George W. Bush.
Leo is also a longtime friend of Justice Clarence Thomas, a 1991 appointee of President George H.W. Bush, and Leo credits Thomas with encouraging him to take an executive post with the Federalist Society in the early 1990s.
After Trump won, Leo visited the president-elect at Trump Tower in November 2016 to talk judges.
“What do you care about? What do you want?” Leo asked Trump during that meeting. Leo later recalled in an interview that Trump said he was looking for candidates with impressive credentials and individuals who would be as hard-right as advertised.
Trump, for example, criticized Justice David Souter, the George H.W. Bush appointee who amassed a liberal record; in 2012, when Chief Justice John Roberts voted to uphold Obamacare, Trump blasted him on social media. Trump, in the private meeting and in public, said he wanted jurists in the mold of the late Antonin Scalia, who had died in early 2016, creating the high court vacancy. The president continues to praise Scalia today.
Leo and the Federalist Society helped deliver Trump the judiciary he wanted. He even
connected Trump to Maureen Scalia, widow of the justice. She was on hand when Trump in January 2017 unveiled the Gorsuch nomination for his seat. Barrett, Trump’s third appointee, had served Scalia as a law clerk.
The selection process, as established in the first Trump administration, was tightly controlled by former White House counsel Don McGahn, who worked closely with Leo.
They deliberately sought out Federalist Society members. McGahn remarked in one 2020 appearance that critics of the conservative group “frequently claim the president has outsourced his selection of judges. That is completely false. I’ve been a member of the Federalist Society since law school, still am, so frankly it seems like it’s been in-sourced.”
In a separate appearance, McGahn added that most of the lawyers in his White House counsel office were members of the group founded in the early 1980s: “Candidly, we’re inside the counsel.”
In the end, Trump appointed one-third of the Supreme Court’s nine justices during his first term. He also filled about 30 percent of the powerful US appellate court seats. He named about a quarter of the US district court seats at the time. One of his lower court appointees was Judge Timothy Reif to the US Court of International Trade, which this week rejected Trump’s tariff plan.
On average, his appointees were younger than those of his predecessor Barack Obama and those of successor President Joe Biden.
That means the lifetime appointees from Trump’s first term will be serving long after he leaves his second term.
And although there has been the occasional decision that veers off the rightward path, the Trump appointees have overwhelmingly reinforced the conservative agenda.
Deputy White House chief of staff Stephen Miller told CNN on Friday that Trump is no longer using the Federalist Society to screen candidates for the bench.
Leo, when asked to comment on Trump’s remarks, said in a statement Friday: “I’m very grateful for President Trump transforming the Federal Courts, and it was a privilege being involved. There’s more work to be done, for sure, but the Federal Judiciary is better than it’s ever been in modern history, and that will be President Trump’s most important legacy.”
