For the last quarter of a 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, well, 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, I ask Leo about all of it: his relationship with Trump and their falling-out (though he disputes this characterization), and how he understands the divide on the right between the old guard like himself and the new characters like Elon Musk and RFK Jr.
I also ask about his so-called dark money groups, a $1.6 billion gift he was given, and the criticism he gets for wielding power and influence of this magnitude.
I ask about Trump’s willingness to defy the courts, if Leo even sees it that way, and if it alarms him. I ask about Trump’s controversial moves like sending accused gang members to El Salvador, and what those choices mean legally. I ask why MAGA has rejected Amy Coney Barrett, and whether gay marriage is settled law—not that I have any vested interest in this one. And most importantly, I ask whether the Supreme Court can remain above the fray.
It was such an original and enlightening conversation that we’re doing something we basically never do: publishing an entire edited transcript of our interview, which comes to some 13,000 words, only for paid subscribers. Listen to the episode by clicking below, or scroll down to read the entire discussion. I hope you find this conversation as fascinating as I did.
