The Influencers: The People Shaping Trump’s New Washington
This story is part of a series exploring the backgrounds and agendas of the players — the well known names and behind-the-scenes operators alike — who will wield power in Trump’s second term.
Last July, Terry Schilling, a conservative activist who had yet to interact with Donald Trump outside of a photo line, flew to Mar-a-Lago to meet with the presidential candidate. A buoyant 38-year-old with spiky hair, Schilling runs the American Principles Project, a group of social conservatives that bills itself as “America’s top defender of the family.” Trump, in the final months of the campaign, had set aside time to participate in an APP documentary that aimed to show how “woke military policies” had weakened the country.
But Schilling had more on his mind that day than the documentary. After filming Trump for 45 minutes, Schilling took him aside and showed him some data from the previous midterms. That election cycle had been a disaster for the GOP, yet Schilling believed APP had garnered numerous votes for Republicans in Arizona and Wisconsin — more than 30,000 in each state — thanks to a paid media blitz on what he called the “trans sports issue.” (The Trump White House didn’t respond to multiple requests for comment for this piece.)
Trump, of course, was already well aware of this topic. Days earlier, at the GOP convention in Milwaukee, he had told his supporters, “We will not have men playing in women’s sports — that will end immediately.” But if anyone was well-positioned to remind Trump of this issue’s political potential, it was Terry Schilling.
Long before the Trump campaign aired an ad with the tagline “Kamala Harris is for they/them, President Trump is for you”; before an analysis by a pro-Harris super PAC showed that a version of the ad featuring radio personality Charlamagne tha God moved the race nearly 3 percentage points in Trump’s favor; before Trump’s victory spawned a civil war among Democrats over whether the party should abandon, or at least modulate, its support of trans rights; before Trump signed executive orders meant to prevent transgender women from participating in female sports and declaring the government would recognize only two genders; before the administration clashed with the governor of Maine over trans rights and banned trans service members from the military — a decade before all of that, Schilling had a hunch about the future of social conservatism. He saw that, once same-sex marriage had become fully legal, social conservatives would need a new electoral battlefront — and opposing the burgeoning transgender-equality movement was what it had to be.
“We were the only group in campaigns and elections on it,” Schilling told me recently. “We started talking about transgenderism in 2015, maybe even before that.”
That year was a turning point for APP, which in those days, according to Schilling, was “an orphanage of important ideas.” Pension reform. The gold standard. Dismantling Common Core. Around that time, APP’s largest donor informed the group that it would need to scale back funding. “‘You’ve got to really make a decision about what you want to do,’” Schilling recalled being told. “And so we did.”
Schilling, who joined APP as political director in 2013 and became the group’s president in 2020, certainly isn’t the only person who helped make opposition to trans rights a focal point of contemporary conservatism. But over the past decade, he has been both a driver and a beneficiary of a remarkable shift in the politics of gender identity.
“Terry and American Principles were the first to convince people, legislators, think-tank types [about] combating transgender ideology,” Heritage Foundation President Kevin Roberts told me. “The bottom line is that a lot of groups that were more focused on free market questions, tax policy … realized they also have to join Terry and American Principles in fighting that fight.”
Tina Descovich, a co-founder of Moms for Liberty, the grassroots organization that backs “parental rights” candidates on school boards, cites Schilling as an influential partner in seeking to use Title IX against transgender rights in schools. “Terry and his group were fighting right alongside us in some of the key swing states,” Descovich told me. “They were running millions of dollars in ads, and we were doing the grassroots work.”
Today, the 30-second political ads on bathroom bills and transgender high-school athletes that Schilling helped to pioneer are a major political factor — in a way that arguably would have been difficult for establishment strategists, even conservative ones, to imagine just a few years ago. Marjorie Dannenfelser, the president of Susan B. Anthony Pro-Life America, credits Schilling with pushing Republicans out of their comfort zone on cultural issues. “Terry is a master at diagnosing where the possibilities are based on the popular will and how to get there,” she told me. “Over-caution is the enemy. And locating where real people are outside of political circles is how you move the ball.”
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Last month, Schilling was trying to talk to me about his friends in the Trump administration over the screeching of a small child. “We’ve actually started creating our own ‘plum book’” — an old-school term for a Rolodex of people with “plum” jobs — “based on all our connections over there,” Schilling told me over the phone. “Because I have a hard time keeping track of them — along with my seven kids.” Those kids range in age from 1 to 19, and Schilling, who lives in Fairfax County, Virginia, and normally works out of APP’s office in Arlington, was home that day on childcare duty while his wife had a root canal.
Schilling is no stranger to the chaos of an extremely full house. The oldest of 10 from a Midwestern Catholic family, he was put to work at his family’s pizza shop, Saint Giuseppe’s Heavenly Pizza, in Moline, Illinois, before he was old enough to drive. He went off to Catholic college at Franciscan University in Steubenville, Ohio, where he described his major as “college Republicans.”
Schilling interned with GOP presidential and U.S. Senate campaigns before turning his attention to his own family’s political fortunes: In 2010, his father, Bobby Schilling — a small-business owner and former crack addict who had also, at one point, been a Democrat — ran for Congress amid the Tea Party backlash to Barack Obama. Bobby Schilling was often compared to Samuel “Joe the Plumber” Wurzelbacher, the Ohioan who confronted Obama over the economy during a campaign stop. Except that unlike Wurzelbacher, Bobby — with Terry serving as campaign manager — won his House race against a Democratic incumbent.
Bobby ran with a populist economic message, but also didn’t shy away from his faith or cultural issues. Terry calls his father “Trump before Trump” — a comparison that works, on some level, if you don’t think about it too deeply. (Trump is a populist, but certainly not a devout pizza shop owner from the Quad Cities.) “My dad had this working-class, pro-free market, protections-for-workers agenda,” Terry recalled, “while also being socially conservative, protecting the unborn, protecting traditional marriage and protecting children and their innocence.”
Two years later, though, Bobby lost reelection to Democrat Cheri Bustos. Republicans blamed redistricting, but Terry seized on another theory: He thinks the campaign should have attacked Bustos harder when she called Bobby “extreme” for backing a GOP bill that seemed to make a distinction between rape and “forcible rape” with respect to banning taxpayer subsidies for abortion. Terry wanted to go scorched earth on Bustos, calling her an extremist for supporting so few restrictions on the procedure. Schilling was frustrated that not everyone in his dad’s orbit agreed.
And he is still annoyed about this: “That really told me that, like, just because you have Hill experience, just because you’re an expert in D.C., it doesn’t mean you actually know anything. And it definitely doesn’t mean you’re right. And so that’s kind of informed everything I’ve done in this town. Anything is possible if you work hard enough and you come up with something smart.”
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On the heels of his father’s defeat, Schilling moved to Washington and joined APP, which had been founded four years earlier by strategist Frank Cannon, legal scholar Robert P. George and GOP candidate Jeff Bell as a conservative bulwark against the liberalism of the Obama era.
It was not an auspicious time for social conservatives, and Schilling — with good reason — worried about the party “completely capitulating on LGBT issues.” State by state, the right was rapidly losing the gay-marriage debate — and in 2015, the Supreme Court would effectively end the argument by legalizing same-sex marriage nationwide. In 2014, Time magazine published its famous “Transgender Tipping Point” piece; the next year, Vanity Fair put Caitlyn Jenner on its cover. It seems almost impossible to believe now, but in his 2016 GOP convention speech, Trump said, in the context of denouncing radical Islam, “I will do everything in my power to protect our LGBTQ citizens from the violence and oppression of a hateful foreign ideology” — then, upon receiving sustained applause, added, “And I have to say, as a Republican, it is so nice to hear you cheering for what I just said.”
Even in Schilling’s telling, it can be tough to get to the bottom of why he latched onto this specific issue. He describes it as a mix of gut instinct, moral conviction and actual data — with a strong emphasis on the latter. To determine next steps after the same-sex marriage decision, Schilling convened market research panels to gauge “consumer” sentiment on political messages, and one thing kept jumping out. “We tested a bunch of different things, and what we kept finding was that all those negative aspects about putting gender identity into civil rights law were very unpopular,” he said.
He began cutting ads — at first, without much success. The earliest ones focused on the 2016 gubernatorial race in North Carolina, the first state to pass an anti-trans bathroom bill. GOP Gov. Pat McCrory, a supporter of the law, lost his reelection bid that year to Democrat Roy Cooper after bathroom-bill detractors argued the law would harm the local economy. “Even though we had plenty of polling that showed people largely agreed with the bathroom bill, because of the influence campaign and businesses threatening to leave, the left showed they had a playbook that worked,” said a former APP staffer whose current job precludes speaking on the record.
Why didn’t the APP ads succeed? “I think [voters] were probably skeptical of this type of thing happening. That was something we ran into early on transgender messaging — just disbelief,” this person said. “And then over time, as more stories were written, more anecdotes were put out there, that changed.” In 2019, APP debuted sports messaging in the Kentucky gubernatorial race between GOP incumbent Matt Bevin and Democrat Andy Beshear. Thanks to APP, voters were now being asked whether it was fair to have an athlete who “claims they’re a girl but was born a boy” playing female sports.
Beshear won, but Schilling says the media blitz shrank Bevin’s losing margin. “We compared the people that saw our ad versus a control group of people that never saw our ad, and we found we shifted 26,000 votes by spending only $600,000,” Schilling told me. “I went back to my donors and said, ‘Listen, we came up short. It was very close. But this really works. It moves voters away from Democrats.’”
Soon, APP was also turning the screws on Republicans. In 2021, the group targeted South Dakota Gov. Kristi Noem who, fearing backlash from the NCAA, had vetoed a bill that would have prevented trans women from competing in women’s sports. A year later, Noem signed an almost identical version of the bill into law. APP applied the same playbook to Greg Abbott in 2022, when the Texas GOP governor wouldn’t support a bill declaring sex-change surgery for minors child abuse. According to Schilling, Abbot got behind it after APP began running ads against him on Fox News.
“You know, sometimes we’re winning over the conference by just showing them the water’s warm,” said Schilling, who takes credit for helping usher bills banning trans women from women’s sports in 26 states. “The American people are in. The voters are behind you.”
By 2024, pro-GOP super PACs beyond just APP were spending millions to ask voters in Montana, Ohio and Nevada whether they wanted to reelect Democratic senators who supported allowing “biological men in girls’ locker rooms.” APP also ran its own ads targeting the Harris-Trump race, piggybacking off the “they/them” push. But for the first time, due to market saturation, APP had no real idea how many votes it alone had moved for Trump — which, for Schilling, was a pretty good problem to have.
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Progressive activists, needless to say, regard Schilling’s work with disgust. Cathryn Oakley, senior director of legal policy at the Human Rights Campaign, accused Schilling and his allies of “fear-mongering around trans kids and using people’s lack of understanding about what it means to be trans” to advance the right’s agenda. “His rhetoric shows absolutely no compassion for these kids, no sense of reality,” she said.
Schilling, of course, rejects that characterization, arguing it’s not the kids and their parents he’s against. “I would separate out the politicians and the people. That’s a very important distinction,” he told me. “The politicians have no excuse for not knowing what’s actually going on. The politicians and the profiteers, that’s the evil part of this movement. But there are a bunch of just, you know, nice people who just really don’t know how devastating this is.”
People who’ve worked for Schilling describe him as a humane boss and a “true believer” with boundless energy for conservative causes. Roberts, the Heritage Foundation president, called him “unfailingly cheerful,” which is rarely how anyone in D.C. describes someone else from D.C. Dannenfelser, who runs the nation’s preeminent anti-abortion advocacy organization, which she called a sister organization to APP, regards him “like a son.”
APP’s super PAC appears to be thriving under Schilling’s leadership. It has gone from raising around $1 million per election cycle a decade ago, according to Federal Election Commission filings, to bringing in almost $13 million in the 2023-2024 cycle, much of it from GOP megadonor Richard Uihlein’s Restoration PAC. Schilling said he hopes to raise another $10 million to $20 million ahead of the midterms.
As APP’s influence has grown, so has Schilling’s personal brand. “The White House takes our work very seriously,” he told me, noting that he had met with Trump’s domestic policy council. “It’s not a coincidence,” Roberts said, “that Terry, still in his relative youth, has gained such influence among the highest elected officials, starting with President Trump, who loves him, and Speaker Johnson, who considers Terry a confidant.”
Schilling’s work on trans issues isn’t done. He still wants Congress to take up legislation codifying anti-trans policies, like barring surgery and gender-affirming care for minors, or defunding them as much as possible at the federal level. And beyond that? To the extent that he’s regarded as someone able to divine, or manipulate into existence, the next cultural backlash, Schilling doesn’t seem to have a firm handle yet on what that might be. He’s spoken publicly about the challenges, like declining economic opportunity and marriage rates, facing boys and men. Recently, APP has gotten behind the push for states to pass age verification for online porn. But as far as culture wars go, it’s an issue without compelling characters, no heroes and villains. No one is really against keeping children away from porn.
For now, though, Schilling has much to celebrate. Back in February, he was invited to the White House for the signing of Trump’s “Keeping Men Out of Women’s Sports” executive order, which had been an APP goal during the election. Schilling doesn’t appear in many, if any, media photos of that day, but he didn’t necessarily need to be front and center. “He’s definitely in the circle of influence,” said Descovich, who was also at the signing. “Everybody knows that he’s playing a role.”
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Liz Skalka is a political reporter based in Maryland.