For the last quarter century, an Italian macher from New Jersey has been one of the most powerful people in the United States. If you’re a certain type of nerdy, obsessive, legally inclined conservative, he’s basically Taylor Swift. But most people don’t know who he is because he doesn’t want them to know.
He has never held or sought political office. He does not hail from Silicon Valley or Wall Street. He is not a writer, pundit, or political aide. He rarely does interviews. And yet his influence is hard to overstate. People in power—particularly presidents—trust and listen to him.
I’m talking about Leonard Leo, the animating force behind the Federalist Society and the key node of a growing network of conservative groups aiming to reshape the culture and the country. Whether you’ve heard of him or not, he has no doubt directly affected your life in some way.
Leo is the person who counseled George W. Bush to appoint Justices John Roberts and Samuel Alito. He had an arguably even greater influence on President Trump. Trump was new to Washington when he first became president. Leo, on the other hand, knew everyone in town. Leo counseled Trump and helped pick and prepare Neil Gorsuch, Brett Kavanaugh, and Amy Coney Barrett for confirmation.
And that’s just the Supreme Court. Leo has cultivated talent across every level of the judicial system.
Leo understands the levers of Washington. He understands how Congress works, how the press works, and most importantly, how the courts work. He is, in a sense, the architect of the Supreme Court’s conservative majority — the one that overturned Roe v. Wade. Which means he has changed American history—for better or worse, depending on your worldview.
Today on Honestly, Bari asks Leo about all of it: his relationship with Trump, their falling out (though he disputes this characterization), how he understands the divide on the right between the old guard like himself and the new characters like Elon Musk and RFK Jr. Bari asks about his so-called dark money groups, the $1.6 billion-dollar gift he was given, and the criticism he gets for wielding power and influence of this magnitude.
She asks about Trump’s willingness to defy the courts, and if Leonard sees it that way. They discuss Trump’s controversial moves like sending accused gang members to El Salvador and reinstituting TikTok. She asks why MAGA has recently rejected Amy Coney Barrett, and if gay marriage is a settled matter.
And most importantly, in a moment of institutional crisis in American life, Bari asks whether the Supreme Court can remain above the fray.
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