Most people have never heard of Leonard Leo. Yet he’s shaped the courts, policies, and even the future of American law more than nearly any public figure in the last 20 years. His influence reaches from the Supreme Court to state judge races, and now he’s setting his sights on the media world—and possibly your favorite shows and feeds.
Leonard Leo orchestrates the transformation of America’s judicial system from behind the scenes, relying on an ocean of dark money and connections. If you care about the Supreme Court, Project 2025, or the slow march of conservative legal changes, you need to know who he is. For a comprehensive look at his influence, check out ProPublica’s deep profile on Leonard Leo.
Early Life and Education: The Making of a Legal Power Player
Leonard Leo was born in 1965 in Long Island, New York, into an Italian-American family that valued hard work and perseverance. His grandfather, an Italian immigrant, started as a tailor and made his way up to vice president at Brooks Brothers. Yet, Leo’s lessons in family pride didn’t translate into inclusive values—his worldview became insular and combative early on.
After his pastry chef father died while Leo was in preschool, his mother remarried and moved their family to New Jersey. Even then, classmates saw Leo as a standout. He wore suits to high school and was labeled “most likely to succeed.” Alongside his future wife, Sally Schroeder, he seemed destined for big things.
He attended Cornell University, where he quickly fell under the influence of government professors who championed originalism—the legal belief that the Constitution should be interpreted using only the meanings understood at the time it was written.
Originalism: A legal principle saying the Constitution’s meaning should remain fixed as understood by its authors in the late 1700s.
At Cornell’s law school, Leo founded a chapter of the Federalist Society, a budding club for conservative law students. This society would become his launchpad to national power, aiming to push back against what its founders called “liberal dominance” in law schools.
Key early milestones:
- Born 1965, Long Island, NY
- Attended Cornell University and Cornell Law School
- Founded college chapter of the Federalist Society in the late 1980s
Read more on the Federalist Society’s background and influence.
Building the Conservative Judicial Machine
Federalist Society Expansion
After law school, Leo never practiced as a lawyer. Instead, he became the Federalist Society’s first D.C.-based employee. Under his guidance, the group stopped being a college club and grew into a powerful pipeline for conservative judges and lawyers.
Leo’s knack for recruitment and fundraising brought in major donors—from corporate giants like Google to billionaires like the Koch brothers. By 2024, membership swelled to over 90,000 attorneys, judges, and law students across the country.
The Society became the vetting ground for federal judges. It offered networking, mentorship, and career growth for conservative legal minds, shaping a generation of judges who would go on to interpret the law in line with Leo’s ideals.
Judicial Confirmation Network and Supreme Court Power Plays
To make sure its preferred judges got confirmed, Leo helped launch the Judicial Confirmation Network (JCN) in 2005—a nonprofit designed to push for Senate approval of right-leaning judges. With substantial, undisclosed financial backing, JCN became a key weapon in confirmation battles.
JCN’s tactics quickly proved effective. It lobbied against nominees considered too moderate or insufficiently loyal to Federalist Society ideals. It poured money into ad campaigns and political pressure, targeting both national figures and local politicians.
Supreme Court Justices confirmed with Leo’s help:
- John Roberts (Chief Justice, 2005)
- Samuel Alito (2006)
- Neil Gorsuch (2017)
- Brett Kavanaugh (2018)
- Amy Coney Barrett (2020)
JCN launched name changes, first to Judicial Crisis Network, then to Conquered Fund, reflecting shifting strategies but the same underlying mission. For more on its evolving influence, see Mapping the Judicial Crisis Network’s role in court appointments.
Simple timeline of Supreme Court maneuvering:
- 2005–2006: Blocked moderates, pushed Roberts and Alito successfully
- 2016: Spent millions ensuring Obama’s nominee Merrick Garland never got a hearing after Antonin Scalia died
- 2017–2020: Bolstered Gorsuch, Kavanaugh, Barrett confirmations with massive ad buys and advocacy
State Courts Influence
Leo’s behind-the-scenes approach didn’t stop at the Supreme Court. He poured resources into state and local judicial elections, often turning low-profile races into million-dollar contests.
In Wisconsin in 2015, his fingerprints showed up on a state Supreme Court ruling that halted a campaign finance investigation against then-Governor Scott Walker. The conservative-majority justices, tied to Leo’s network, ordered evidence against Walker destroyed. This quiet manipulation of state courts has repeated itself across the country, aided by Leo-affiliated dark money funneled into attack ads, advocacy groups, and direct campaign support.
As money from these networks exploded after the Citizens United decision (which allowed corporations unlimited political spending), so did Leo’s national influence—turning once-local judge races into battlegrounds for America’s legal direction.
The Luxurious Lifestyle: Gifts, Influence, and Ethical Questions
Leo isn’t shy about using his connections to reward judges. He connects top legal figures to perks most Americans can only dream about—luxury vacations, private jets, elite social events, and billionaire friendships.
Billionaires in Leo’s circle:
- Paul Singer (arranged luxury fishing trips with Justice Alito)
- Robin Arkley (provided private flights)
- Harlan Crowe (financed lavish travel for Justice Clarence Thomas and his wife)
These perks aren’t simply generous gestures. They raise huge ethical and legal questions. For example, Paul Singer’s finance firm later took cases to the Supreme Court after wining and dining justices, yet Samuel Alito didn’t recuse himself. Leo also played a role in opaque payouts to Ginni Thomas (wife of Clarence Thomas), arranging that her name not appear on records.
Investigative reports, including those by ProPublica on undisclosed judicial gifts, fueled Senate subpoenas and national outrage. Leo thumbed his nose at subpoenas, blaming “the left’s dark money” for scrutiny. Meanwhile, the Supreme Court’s Chief Justice John Roberts responded with only modest, voluntary new “ethics standards,” which many saw as window dressing.
Dark Money and Political Power: Funding Trump’s Judges and Beyond
Between 2014 and 2020, organizations associated with Leonard Leo raised over $600 million for conservative legal battles, with donations pouring in from wealthy right-wing patrons. These accounts operated in secret, never disclosing donors, and funded not only Supreme Court wars but also campaigns against liberal state judges and support for anti-abortion and anti-LGBTQ policies.
When Trump ran for president, Leo moved swiftly. He handed Trump a list of Federalist Society-approved nominees, ensuring that the president’s judicial appointments would advance Leo’s priorities.
- 231 judges appointed by Trump in his first term
- 86% of them were Federalist Society members or alumni
Leo’s network isn’t just big—it’s nearly bottomless. In one especially jaw-dropping move, Chicago businessman Barre Seid gave Leo control of $1.6 billion by donating his business via the Marble Freedom Trust. This windfall was structured to avoid around $400 million in taxes, raising eyebrows at every level of government. Coverage by Axios explains the rise of CRC Advisors under Leo.
CRC Advisors and other nonprofits shuffle funds between one another, making oversight almost impossible and ensuring Leo remains flush for his next political play.
Cafeteria Catholicism and Personal Life: Faith, Family, and Contradictions
Leonard Leo is proudly Catholic, though many say he cherry-picks the faith’s teachings to suit his political aims. He’s staunchly anti-abortion and supports policies that restrict reproductive rights, yet he’s conspicuously silent on Catholic stances supporting the poor, immigrants, workers, or climate stewardship.
He’s closely connected to Opus Dei, a controversial, secretive wing of the Catholic Church associated with hardline conservative values. Leo donates generously to their schools, sends his children there, and has supported their D.C.-area Catholic Information Center.
Contradictions between faith and action:
- Anti-abortion, but little advocacy for helping poor families or supporting healthcare
- Donates to expensive elite causes while Catholicism urges help for the less fortunate
- Backs environmental rollbacks, ignoring Pope Francis’s climate guidance
Perhaps the most personal element of Leo’s story centers around the tragic loss of his oldest daughter, Margaret Mary Leo, who died young from complications of spina bifida. In her memory, Leo and his family circulated prayer cards featuring her image, with symbolism suggesting a campaign for her eventual sainthood.
After Roe v. Wade was overturned, Leo’s opulent mansion in Maine became the site of regular protests—mainly older women standing in opposition to his role in rolling back reproductive rights. Leo has claimed that such protests are attacks on his faith rather than his political actions. For a window into Leo's Catholic ties and contradictions, read Jacobin’s review.
Sister Joan Chittister, a renowned Catholic nun, put it this way:
“I do not believe that just because you’re opposed to abortion that makes you pro-life. If all you want is a child born, but not a child fed or housed or educated, that’s not pro-life. That’s pro-birth.”
Expanding Into Culture: Targeting Entertainment and Media
Leo’s ambitions don’t stop at the courthouse steps. In 2021, he took over as chair of the Teneo Network, described as a conservative “talent pipeline” for Hollywood, Silicon Valley, and beyond. Leo’s hope is to build a group of industry insiders who echo his views and push back against progressive trends in film, TV, and tech.
Teneo Network’s connections include:
- Senator Josh Hawley (Missouri)
- Vice President J.D. Vance
- Media influencers Charlie Kirk and Ben Shapiro
- Jonathan Bunch, Leo’s right-hand man
He’s spent millions promoting campaigns for public figures he admires, such as Supreme Court Justice Clarence Thomas. In one documented case, Leo’s groups bankrolled a $1.8 million online blitz to make it seem like Thomas had enthusiastic grassroots support. Fan websites and social accounts, run by Leo-affiliated entities, worked to improve Thomas’s public image—sometimes clumsily, as even Thomas seemed out of the loop on who ran them.
Leo’s move into pop culture hasn’t always gone well. A major push behind the documentary film Created Equal: Clarence Thomas in His Own Words flopped at the box office, despite deep investment. These campaigns highlight the gap between political muscle and cultural impact. ProPublica’s exploration of Leo’s Teneo campaigns reveals more.
Recent Electoral Battles and Judicial Setbacks
In recent years, Leo shifted considerable resources into state-level races, especially in Wisconsin. The stakes? Control over voter rights, abortion law, and political maps—issues just as consequential as Congressional races.
But the playbook didn’t always work. In Wisconsin’s high-profile 2023 Supreme Court election, Leo and his allies spent huge sums to back conservative judges. Yet, progressive coalitions matched or outspent him, out-organized the right, and flipped key seats to the left. Judges aligned with Leo’s vision lost, flipping the court’s balance for the first time in years.
Key Wisconsin court races influenced by Leo:
- 2020: Dan Kelly loses after $1 million spent in one week by Leo’s network
- 2023: Dan Kelly loses again to liberal candidate Janet Protasiewicz
- Result: First liberal majority on Wisconsin Supreme Court in a decade, with record campaign spending
These defeats exposed that Leo’s money and influence have limits, especially when public awareness and opposition are high. For the inside story on these electoral showdowns, see Mother Jones on Leo's judicial battle in Wisconsin.
Leonard Leo’s Legacy and Character
How should history judge Leonard Leo? Is he a scheming sociopath or a true-believing zealot? In the words of the Hysteria podcast hosts, he’s a “scheme-based person,” driven by self-interest but also a deep belief in his own vision. He’s built and weaponized a dark-money machine that has left a lasting mark on the courts and the nation.
“He’s done more to hurt this country than most people.”
“His entire personality is built around the idea that he is somehow oppressed, and that other people’s personal choices are happening to him because of a religious faith that props up his own sense of aggrieved entitlement.”
Leo’s reach is undeniable. Whether you agree with his politics or not, his impact on the American legal system will endure for decades. As the hosts put it:
There’s no hate quite like Christian love.
Additional Resources and Further Reading
Want to dig deeper into Leonard Leo’s world? These respected investigations and reports offer more context:
- ProPublica’s reporting on Leonard Leo and the Supreme Court
- Rolling Stone’s expose on Leo and Opus Dei
- Washington Post: Leonard Leo’s Supreme Court connections
- Jacobin’s look at Leo’s Catholic activism
- Axios on Leo’s firm CRC Advisors
For anyone concerned with the courts, democracy, and the future of American rights, understanding Leonard Leo isn’t optional. He’s working quietly, but his influence is everywhere. Stay informed and keep an eye on who’s working behind the curtain.
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