How Leonard Leo and Peter Thiel Handed Trump to the Heritage FoundationInside the billionaire pipeline that turned a think tank
Leonard Leo is the man who handpicked half the Supreme Court. The other half he helped. Starting with his friendship with SCOTUS Judge Clarence Thomas in the 1990s. Leo has never argued a case, never worn a robe, and never held public office. But his fingerprints are all over the death of Roe, the gutting of the Voting Rights Act, and the rise of a court infiltrated by Trump loyalists.
Peter Thiel, meanwhile, is Silicon Valley’s vampire libertarian.. the billionaire who funds AI surveillance for ICE, bankrolls neo-reactionary Senate candidates, and dreams of a world where democracy is optional and oligarchy is optimized. The same man who helped place JD — a man who once referred to Trump as Hitler — as Vice President.
Together, they are not just players in the American collapse. They are co-authors, and the Heritage Foundation is the bridge that turned far-right fantasy into federal reality.
So, Who Is Leonard Leo?
Leonard Leo was born in Long Island in 1965, and from the beginning, he seemed to embody the myth of the all-American overachiever.
His father died when he was a toddler. His mother remarried, and Leo was raised in the bland suburbs of New Jersey. He wore ties to school, spoke in polished phrases, and built his identity around Catholic conservatism and raw ambition. His classmates called him the "Moneybags Kid" because even as a teenager, he knew how to raise cash, curry favor, and run a room.
But this was no harmless prep school hustle. That reputation for fundraising and calculated charm would become the foundation of one of the most powerful political influence operations in modern American history.
He went on to Cornell University and then Cornell Law School, and when he realized Cornell didn’t have a chapter of the new Federalist Society, he started one. One that he briefly put on pause to help his friend, SCOTUS Judge Clarence Thomas, secure his seat on the Supreme Court in 1991.
That experience was a turning point. It showed Leo how judicial politics could be waged like a campaign.
Shortly after, while interning in D.C., Leonard Leo heard Reagan’s Attorney General, Ed Meese, preach the gospel of originalism a legal philosophy that would become Leo’s holy text.
Originalism, at its rotten core says, “Let’s interpret the original Constitution based only on how it was understood when it was written in the 1700’s.”
Why does every power-hungry white guy use a half-baked cult doctrine to justify their empire of evil?
It’s kind of ironic because originalists don’t even follow just one “original” Constitution. They cherry pick which amendments they believe in.
One day it’s 1789 to limit voting rights. Another day it’s 1791 to protect guns. They say it's about the Founders, but it’s really about keeping power out of your hands and in the hands of white, rich men. They treat gun rights as sacred because people in 1791 had muskets but abortion, LGBTQ+ rights, and voting protections don’t count, because those didn’t exist in 1868. They think the EPA and CDC are unconstitutional, but billionaires pouring money into elections is just “free speech.”
Even birthright citizenship is up for grabs if it involves immigrant families.
With early funding from billionaire families with foundations like the Olins, Bradleys, and Scaife, Leonard Leo transformed the Federalist Society from a debate club into a judicial insurgency. It was more than just a pipeline for judges. It was a breeding ground for conservative ideology.
This lead to him being known as the “judicial kingmaker.”
Although never sitting on the bench himself, Leo handpicked Neil Gorsuch, Brett Kavanaugh and Amy Coney Barrett. Before that, he’d helped pick or confirm the court’s three other conservative justices Clarence Thomas, John Roberts and Samuel Alito.
Leonard Leo, much like the Heritage Foundation, has been playing the long-game of conservative politics. Using “boring” lawfare to rise to the top, and Peter Thiel became one of his ideological foot soldiers during his college years when he joined Stanford’s Federalist Society branch.
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