A Conservative Survives Getting Dumped by Trump

By Maggie Severns, Josh Dawsey and John Jurgensen

“House of David,” a retelling of the biblical shepherd’s unlikely rise, capped season one with the future king’s epic takedown of Goliath and started April in Amazon’s top streaming spot.

David’s surprise triumph was also Leonard Leo’s. The conservative lawyer and cochairman of the Federalist Society has been secretly helping bankroll Wonder Project, a Texas-based studio that produced the popular series and, Leo hopes, will follow with a string of Christian- and conservative-leaning shows so slick they can go head-to-head with other big-budget entertainment.

Armed with a $1.6 billion gift from a Chicago industrialist, believed to be one of the largest single contribution to any politically active group in U.S. history, Leo wants to make America’s culture more conservative. That might sound as quixotic as killing a giant with a sling and a small stone.

But Leo, unbounded by the pressures of re-election or dependence on outside money, is a rare conservative, who, after being cast out of Trump’s inner circle, remains free to pursue his own vision of what will make America great again, leveraging the soft power of mass entertainment and the hard power of the courts.

The 59-year-old, who grew up in New Jersey, has already played a significant role pushing America’s judiciary to the right. Leo advised President Trump in his first term to nominate Federalist Society members Neil Gorsuch, Amy Coney Barrett and Brett Kavanaugh to the Supreme Court. All three now serve.

Leo has since fallen out of favor with Trump, who believes Leo tried to take too much credit for the judicial picks, according to four advisers close to the president. Last week, angry over a string of judicial setbacks, Trump in a Truth Social post blamed the Federalist Society and called Leo a “sleazebag” who “probably hates America.”

In an interview last month, Leo praised Trump for some of his policy efforts but said the administration should follow the “rule of law” in its deportation actions, which in certain cases courts have said deprived migrants of their right to due process. Following Trump’s attack last week, Leo turned the other cheek. “There’s more work to be done, for sure, but the federal judiciary is better than it’s ever been in modern history,” he said.

After years of driving conservative causes in Washing--ton, Leo is betting he can make an even bigger splash in Hollywood, winning over hearts and minds with wholesome tales of entrepreneurship, family unity and inspiring historical figures—young George Washington, for instance, and maybe the Wright brothers. His investments in private entertainment studios and startups take place out of the public eye.

“You can make investments in politics and public policy, but ultimately you’re going to be a lot more successful at that game if social and cultural institutions have the right sort of frame of reference, in terms of what life ought to be like in our country,” Leo said. That will take a new generation of conservative movie makers and likeminded production studios.

Leo is seeding the effort, alongside similarly aimed projects, with millions of dollars flowing through dozens of nonprofit groups and forprofit companies, according to tax and financial documents viewed by The Wall Street Journal and interviews with more than 20 people familiar with Leo’s investments and entertainment projects.

David Axelrod, a former top adviser to President Obama, called it “gilded guerrilla warfare.”

Teneo, one of the groups funded by Leo’s billion-dollar windfall, is a networking club of several hundred conservatives in politics and American corporations, recruited before they hit 40. “We believe that history is not shaped by isolated ‘great men’ or impersonal historical forces. Instead, we believe the heroes of history are well-positioned people working together toward the same goal,” according to a paper explaining its vision. (The group isn’t affiliated with the communications and advisory firm of the same name.)

Teneo has recently recruited roughly 100 members who work in movies, podcasts and entertainment financing, according to a person familiar with the matter. “Out of respect for the privacy of those engaged in the Teneo network, we don’t comment on what happens at events or who participates,” Teneo CEO Amanda Covo said. “But we’re excited about what appears to be many new successful ventures focused on high-quality family entertainment.”

Neither Leo, the companies nor the groups receiving money, including those outside of entertainment, would comment on the largely untraceable investments. Keeping political spending under wraps is a longtime Washing--ton tactic. But Leo’s groups often take extra steps, such as donating money into larger funds that pool many other donations.

“He’s not a poor culture warrior anymore. He’s the generalissimo, and he’s got a big war chest and he doesn’t seem shy about directing it towards things that will benefit him,” said Robert Maguire, research director at the nonprofit Citizens for Responsibility and Ethics in Washington.

Good fortune

Leo joined the Federalist Society as a college student in the 1980s and spent three decades at the organization, which successfully challenged liberal dominance in the legal industry and judiciary. The group trained conservatives, fostered career networking and incubated legal views, once at the fringes, that have since been embraced by Supreme Court justices.

He advised the second Bush administration on judicial appointments and helped promote Supreme Court nominees as early as 2005, when he worked on a multimillion- dollar ad campaign promoting John Roberts, now the court’s chief justice.

He was a close ally of Trump for the first term, helping pick Supreme Court judges and filling the courts with record confirmations. The two haven’t spoken in five years. “Leonard Leo sat on the sidelines with all his money during the four years of lawfare against President Trump,” said Mike Davis, a Trump ally. “And now Leonard Leo is completely on the outs in the second term.”

But Leo received a life-altering fortune in 2020. Chicago billionaire Barre Seid donated all of his shares in Tripp Lite, his electrical products manufacturing company, to a nonprofit that Leo controlled. The company was sold for $1.6 billion the following year, affording more than a billion dollars to manage and disburse.

Leo said he had worked with the 93-year-old Seid over the years, but he declined to say in what fashion. Seid has for decades donated money to conservative groups, but he has never commented publicly on his politics. A representative for Seid didn’t respond to requests for comment.

Mirroring the Federalist Society’s successful strategy, Leo offers the prospect of professional networking and career advancement to attract conservative professionals. Teneo, one of the groups funded through Seid’s gift, has since its inception recruited C-suite executives on Wall Street and in Silicon Valley, one member said.

Teneo, founded in 2008, never raised more than a million dollars in a year until Leo took an interest in the group about five years ago. By 2023, it had grown into a $7 milliona- year organization. Under Leo’s guidance, Teneo has put resources into a subgroup focused exclusively on entertainment. It convenes its own conference each fall in Nashville, Tenn., which has become the hub for a new wave of conservative and Christian filmmakers, including two of its biggest luminaries, the brothers Andrew Erwin and Jon Erwin, both Teneo members. Jon Erwin’s studio, Wonder Project, “House of David.” Teneo conferences are relaxed gatherings where members build friendships and make professional connections. The entertainment group visits wineries and has heard talks, for instance, on how to build a podcast audience. Moviemakers get a chance to pitch projects to conservative funders.

Like the Wonder Project, some companies run by Teneo members get money from Leo’s network. Sycamore Studios is one. The children’s entertainment studio aims to draw a mass audience while keeping free of progressive views on diversity, gender or homosexuality.

“If parents trust a movie, they’re happy to put it on again and again,” Sycamore Studios co-founder Timothy Reckart wrote recently in the religion-focused magazine First Things. “This spares them the effort of making sure the movie is family-appropriate every time.”

The studio has hired the writers of two “Paw Patrol” movies to produce its first film, an animated adaptation of “Doctor Dolittle,” a character who can speak to animals and whose adventures echo the innocence of other children’s books published in the 1920s and 1930s.

A former Marvel Studios executive has signed on with Sycamore for an adaptation of the graphic novel ‘‘Zita the Spacegirl,” about a heroic girl on an intergalactic quest to rescue her best friend from an alien doomsday cult. Neither film will be explicitly Christian or conservative.

The Moving Picture Institute, an education-and-entertainment nonprofit with ties to Leo, has meanwhile produced a string of successful indie movies with libertarian themes. One is based on a true story about a journalistturned- pinball player who battled to overturn a decadeslong ban in New York City. Its denouement features a pinball game played at city hall.

The film, which boasted an up-and-coming star in Mike Faist, won awards on the film festival circuit and streaming TV distribution—all markers of relative success for a smallbudget indie movie. A New Yorker reviewer said it offered a “vibrantly scrappy re-creation” of 1970s New York and ranked it as one of his top 10 movies of 2023. Another Moving Picture Institute film that toured the recent film-festival circuit was “Freedom Hair,” a story drawn from real life about a woman whose hair-braiding studio in Mississippi runs into trouble with the law over the state’s arduous occupational licensing laws—a libertarian- tinged tale about government overreach.

“If I catch you with this again, I’ll have to close you down and may arrest you,” an officer says to the woman in the movie while holding up a faulty business license.

“On what charge?” the woman retorts, “making a living?”

Leo’s network invests in studios rather than individual movies. Past films with a conservative point of view—“The Passion of the Christ” and “Thank You for Smoking”— grabbed attention but didn’t do much to change Hollywood. Leo and allies are betting that investing in people and movie studios will cement a conservative strain in entertainment culture for years.

While Leo’s goals are longterm, he hopes to spend his $1.6 billion expeditiously.

“We’re not going to be the Ford Foundation to be around forever,” he said. “The goal is to do our work, and at some point in time to decide that we’ve done what we can do and move on.”

Beyond the screen

While Leo is bullish on changing Hollywood, he also is investing millions to change corporate behavior.

For Leo and many Republicans, the wave of progressivism in the wake of the Covid-19 pandemic and the Black Lives Matter movement yielded troubling changes, such as companies rolling out diversity and environmental programs.

Turning away from a traditional laissez-faire approach, Leo and other conservatives set out to discourage such corporate endeavors. Groups like the State Financial Officers Foundation, also connected to Leo’s network, encourage state pension-fund operators to ditch asset managers that have embraced ESG initiatives.

Documents also indicate Leo’s network is tied to Vallecito Capital, a litigation-finance firm whose founder indicated it will fund lawsuits against companies that embraced diversity and sustainability initiatives.

Some of the groups receiving money from Leo employ CRC Advisors, a longtime Republican public-relations firm Leo joined in 2020. Leo “supercharged” the company, CEO Greg Mueller said.

Leo has allocated money to a range of nonprofits including Consumers’ Research, according to sources and tax documents. The nonprofit has run online ads—titled “Stop Corporate Creeps!”—that criticize executives who sit on boards of hospitals that perform sex-change operations.

“If you expose what corporate America is doing, what banks are doing, what financial institutions are doing, what investment advisers are doing,” Leo said, “that will create the kind of awareness where consumers and investors can respond with their buying. With their wallet.”

For now, consumers of popular entertainment are responding. More than 22 million people streamed “House of David” in the first 2½ weeks after its release.

Amazon has given the greenlight to a second season of “House of David,” which is now in production. After dispatching Goliath, according to the biblical account, David embarks on new adventures that lead him to becoming king of Israel and unite his people’s squabbling tribes.

It will likely take at least another season for Leo to see if he can do the same for his.