When Schilling considered the range of issues making centrist voters and suburban parents uncomfortable, the one that stood out to him was transgender rights: an issue that had largely been absorbed into the Democratic platform, but which he suspected many Americans were still processing themselves. But what was the right angle to take? Earlier that summer, American Principles Project had partnered with a behavioral science firm to assess whether focusing on transgender issues could turn educated suburbanites into Republican voters. APP and its data partner, Evolving Strategies, analyzed how thousands of registered Kentucky voters reacted to different messages about what they described as Beshear’s “extreme” support for transgender rights. Should men be allowed to participate in sports events for women and girls? Andy Beshear thinks so. Should men be permitted to use women’s restrooms because they identify as transgender women? Andy Beshear thinks so.

“What we found was the sports issue got the most powerful response from people, specifically conservative Democrats and independents,” Schilling would explain to me later.

In the end, Bevin still lost. But while many Republicans saw the defeat as a worrisome forecast, Schilling looked at the race and saw a vindication for his theory of the case. A postmortem on the Kentucky election commissioned by APP estimated the group’s messaging campaign, which had cost a relatively modest six-figure investment “delivered nearly 13,000 new votes for Bevin” and brought his margin of defeat down from 31,000 to just over 5,000. (The group has used the data to raise money for its continuing efforts.)

“We wanted Bevin to win, but more than anything, we wanted to test this out before trying it at a much larger scale. Now, donors understand that although we came up a few votes short in Kentucky, this can still work. This is persuasive,” Schilling said.

To prove that thesis, Schilling is about to test his message on the biggest electoral stage of all—the 2020 presidential race.

Next week, APP will debut two ads in battleground Michigan that accuse former Vice President Joe Biden, who has generally used his platform to promote protections for LGBTQ youth, of endorsing “gender change treatments for minors,” including surgery and hormone therapies for transgender youth. One of the ads, featuring former drag queen Kevin Whitt, warns that children “need time” to develop a stable sense of their gender. “As a young teen, I felt I should be a woman,” Whitt says. “Seventeen years later, I felt I should be a man again. Treatments to change the gender of a minor are very dangerous and irreversible.”

In a campaign that has already become defined by the president’s controversial defense of Confederate monuments and attacks on anti-racism protesters, Schilling is hoping that stoking anxieties of suburban women and independents about gender nonconforming adolescents will persuade President Donald Trump to add one more front to his culture war reelection strategy.

“The Democratic Party has run circles around us without any opposition because the vast majority of Republicans shy away from these issues in favor of business and tax topics,” Schilling said. “What I’m hoping is that once we release these ads and numbers start to move, the Trump campaign will see it’s a powerful issue that the Republican Party can use to its success.”

There’s no denying the Trump campaign could use some help. Trump’s handling of the economy, coronavirus pandemic and ongoing civil unrest has hurt him badly in the polls, and public fear of infection has thwarted plans for his signature rallies, all of which has enabled Biden to rise almost untouched.

But there is an enormous gulf inside Trump’s circle of campaign advisers and closest allies over whether, even at this fraught juncture, injecting transgender issues into the campaign is a potential key to victory or an act of self-destruction.

A cohort of establishment Republicans, social libertarians and new GOP converts oppose the strategy. Among them are Trump’s son-in-law Jared Kushner and his wife, Ivanka. They point to a raft of evidence—from the volatile bathroom debate in North Carolina that lost the GOP the governor’s race in 2016 to a bitter Republican primary in Pennsylvania’s 2018 gubernatorial race—that pushing anti-LGBTQ issues is slowly destroying the Republican Party, one high-profile race at a time. Kushner, the de facto leader of Trump’s 2020 operation, and Ivanka have previously worked to kill anti-LGBTQ measures inside the White House. One of the president’s favorite officials, former U.S. Ambassador to Germany Ric Grenell, is a gay conservative who helped persuade Trump to use the power of American diplomacy to end the criminalization of homosexuality abroad.

“This might become a hot cultural issue, but it’s not a thing yet. Right now, it’s just an easy issue for the other side to attack us on. They will call us bigots,” said one senior adviser to Trump’s reelection campaign.

But Schilling has a formidable roster of like-minded allies at the highest levels of the Trump administration. Top White House policy adviser Stephen Miller was one of the chief architects of the administration’s transgender military ban in July 2017 and has routinely encouraged Trump to engage in the most polarizing cultural battles in order to rouse his base. And in his previous perch as chairman of the ultraconservative House Freedom Caucus, Trump’s chief of staff Mark Meadows threatened to vote against a spending bill if it omitted the transgender provision, which would have prohibited the Pentagon from subsidizing medical costs associated with gender transitions for military personnel. Two members of the president’s Cabinet, Housing and Urban Development Secretary Ben Carson and Education Secretary Betsy DeVos, have also lamented the inclusion of transgender individuals in gender-segregated sports and homeless shelters. DeVos recently argued that schools violate Title IX, a decades-old law prohibiting sex discrimination in federally funded educational facilities, when they permit transgender athletes to participate in gender-segregated sports. Competing against a transgender woman, DeVos reasoned, “den[ies] a female student a chance to win a championship.”

“I think it could be one stroke of a pen for President Trump to simply say that Title IX … means that females compete in women’s sports and males compete in men’s sports,” said Doreen Denny, vice president of government relations at Concerned Women for America, a group that’s repeatedly praised the president’s job performance and hosted senior Trump administration officials at its promotional gatherings.

The chief executive at CWA, Penny Nance, serves on the president’s “Women for Trump” advisory board and said she has personally encouraged Republican leaders to learn about what she calls the dangerous implications of trans-inclusive sports policies “so they feel comfortable speaking” about the issue themselves. Nance has not had the chance to brief Trump on the issue but said it’s a “clarifying cultural event” she hopes he will lean into.

Schilling has also refrained from making a pitch directly to Trump’s campaign. “I don’t want to cross any lines since we’re touching a very personal issue,” he said when asked why he’s avoided contacting the president’s team. But he also doesn’t want to wait for permission and waste an opportunity to advance a cause that he believes should define the Republican Party going forward. The ads will almost certainly provoke denunciations from the Biden camp, marking a new skirmish in a raging culture war. But can they win?

For some conservatives, the idea of using transgender athletes to win an election looks like a final suicide mission in a war that has already been lost.

For years, it seemed like gay marriage would be a winning issue for the right—Republicans at the state level passed a raft of gay marriage bans in the presidential cycle of 2004—and then, just as suddenly, it wasn’t. The 2015 Supreme Court decision to legalize same-sex marriage in Obergefell v. Hodges capped a seismic shift in public opinion on the issue—effectively ending a messaging battle religious conservatives had spent years waging.

The rights of transgender people, it appears, have followed the same trajectory. In 2016, after eight months of bitter national coverage of North Carolina’s transgender bathroom ban, which required that public restrooms be designated for use based only on one’s biological sex, numerous boycotts and an estimated $196 million in lost tourism revenue, voters washed their hands of Pat McCrory, the state’s incumbent Republican governor who had staked his career on defending the law. Then four years later, conservatives watched with dismay as the Supreme Court again ruled in favor of the LGBTQ community. And it was Justice Neil Gorsuch, supposedly a conservative stalwart, who wrote the majority opinion affirming sexual orientation and transgender status as protected categories against workplace discrimination.

All the while, public opinion was moving dramatically in favor of gay, lesbian or transgender politicians and away from laws and policies treating LGBTQ people differently. Two months after the Trump administration’s transgender military ban took effect last year, a survey by the Public Religion Research Institute showed two-thirds of Americans opposed the policy, including 47 percent of Republicans—up 10 percentage points from when Trump announced the restriction in 2017. And when Pete Buttigieg, the openly gay former mayor of South Bend, Ind., was still competing in the Democratic presidential primary, 70 percent of voters said they would be open to electing a gay president.

“I don’t think it’s going to work,” Jennifer Williams said of Schilling’s plan to use trans issues as a cudgel against Biden. “Four years ago, they were trying to scare everyone by saying young children and women were going to be assaulted in restrooms. That never happened.”

Williams, 52, is a conservative New Jersey Catholic who, at least on paper, could fit right into the circles Schilling runs in. She’s a married Republican, devoted parent, child of a World War II veteran, member of the National Rifle Association and longtime attendee of the Conservative Political Action Conference, a hot spot for grassroots activism and the party’s rising stars. Williams is also transgender. In 2016, she became the first openly transgender delegate to attend the Republican National Convention in Cleveland.

While she wholeheartedly disagrees with Schilling’s strategy, she says she’s more concerned about what it says about her party’s “dangerous betrayal” of both Christian values and individual liberty, which she considers one of the central tenets of conservatism.

“In the short term, some of these groups might get what they want. It will gin up Trump’s base and drive turnout. But if we’re true conservatives, we’re supposed to be about limited government intervention in people’s lives,” she said. “For every voter these scare tactics might get, there will be another voter asking why the president and his allies are focused on transgender children when people are worried about their jobs and whether they can feed their kids and pay their mortgages.”

She added, “I don’t know the president personally, but I would discourage him from reducing my life and the lives of other transgender people to a political gimmick just because his poll numbers are bad right now.”

Some staunch social conservatives who have employed this strategy in their own political careers have learned firsthand how perilous it can be. Before he became Trump’s pick for vice president, Mike Pence backpedaled on a religious freedom measure he had signed as governor of Indiana—a move that was meant to shore up his Christian base before he announced his bid for reelection—after critics argued it would contribute to discrimination against gay individuals. The 2015 measure, known as the Religious Freedom Restoration Act, was billed by Pence as a move to shield Indiana businesses from cumbersome government regulations by allowing owners to cite their religious beliefs as a legal defense. Pence’s conservative allies claimed the move was also necessary to prevent religious workers and business owners from being forced to participate in same-sex nuptials that would violate sincerely held beliefs. But amid passionate opposition from LGBTQ residents, Pence signed off on a legislative fix aimed at preventing businesses from discriminating against people on the basis of their sexual orientation.

“After much reflection and in consultation with leadership in the General Assembly, I’ve come to the conclusion that it would be helpful to move legislation this week that makes it clear that this law does not give businesses a right to deny services to anyone,” he told reporters at the time.

Still, some White House officials and campaign advisers see cultural wedge issues as crucial to energizing Trump’s base and outraging moderate voters, and—like Schilling—think transgender rights is the wedge issue of the moment at a time when many Republicans are hunting for new ways to discredit the progressive agenda as intolerant, in their view, of the average American’s values and truths.

“It’s gross negligence to avoid the transgender debate and treat this suite of issues as irrelevant,” contended one Republican who speaks with Trump regularly.

Back in 2016, fresh off his stunning loss, Pat McCrory spoke to Trump, too.

The president-elect had summoned McCrory to his gilded Manhattan skyscraper one month after the November election to discuss a potential role in his incoming administration. The meeting was cast by Trump’s transition team as a courtesy to the outgoing Republican governor, whom the president-elect had come to know out on the campaign trail. During one part of their meeting, Trump demanded to know more about the bathroom access issue. Vetting documents later showed it was a point of concern for transition officials who had been eyeing McCrory for various Cabinet positions.

“The complexity of the issue makes it difficult to have a sound political discussion for fear of backlash, and he wanted to know more about the issue and why people get so upset,” said McCrory, who has used his bruising experience to counsel elected officials. He told me he gave Trump an early warning.

“I said, ‘If I were you, sir, I would stay out of it.’”

Two episodes, five years apart, reveal puzzling and contradictory clues about whether Trump will take that advice and stay out of it.

In April 2012, Canadian model Jenna Talackova hired renowned women’s rights attorney Gloria Allred to help her bypass a ban on transgender competitors in the Miss Universe Canada contest. The Miss Universe Organization, a parent company of the Canadian offshoot that Trump owned at the time, had previously disqualified Talackova from participating in the pageant after learning of her transgender status. But amid pressure from LGBTQ rights groups and other contestants, Trump relented. He announced his reinstatement of Talackova and a permanent end to the pageant’s ban on transgender contestants.

“We made the decision two days before we even heard that [Allred] was involved,” Trump said at the time, suggesting he might have landed on a different outcome for Talackova had he known about the “third-rate lawyer” she hired for representation. (Trump’s feud with Allred, who at one time represented a woman who accused Trump of sexual misconduct, would continue into his presidency).

That was when he was just a businessman and promoter. In 2017, six months into his term as president of the United States, Trump fired off a string of tweets around 9 a.m.—before many of his aides had made it into the West Wing. “The United States Government will not accept or allow Transgender individuals to serve in any capacity in the U.S. military,” he declared. Five years after his run-in with Talackova, he had decided to pad his new reputation as a trusted conservative leader with a move aimed squarely at his traditionalist supporters.

Despite widespread outrage over the casual format of his announcement, Trump has not wavered on the decision. His administration defended the move all the way to the Supreme Court. Some Trump allies said the president was acting strategically, knowing the ban would delight religious conservatives who had been outraged when the Obama administration ended the military’s long-standing ban on transgender service members shortly before the 2016 election. Others disputed that ideology or politics had anything to do with it. In their view, the ban was nothing but a businessman making a cost-effective decision.

“What happened was Trump’s generals mentioned how much it costs to cover gender transition treatments for active military personnel and he just tweeted and said, ‘Well, that’s over,’” recalled a former senior White House official.

The range of explanations for Trump’s ban on transgender soldiers underscores the conundrum people like Schilling face as they attempt to sway the president on LGBTQ issues. As predictable as Trump can be on matters such as immigration and race, there’s no telling from one day to the next where he will land on LGBTQ rights. Even now, as the president refuses to lift his ban on transgender service members at its 3-year anniversary, his campaign is hawking Pride T-shirts and ballcaps.

It’s been that way for a while. Before overseeing an administration that has rolled back health care protections for transgender individuals, scrubbed government websites of references to “sexual orientation” or “gender identity,” and filed an amicus brief asking the Supreme Court to oppose employment discrimination protections for LGBTQ workers, Trump was being mentored by Roy Cohn, a ruthless political fixer and closeted gay man, lending charitable assistance to groups conducting AIDS research and promising Caitlyn Jenner, the former Olympic gold medalist and Kardashian-Jenner patriarch, she could use whichever restroom she preferred in Trump Tower. “People go, they use the bathroom that they feel is appropriate. There has been so little trouble,” Trump said during an April 2016 appearance on NBC’s “Today” show, one year after Jenner came out as a transgender woman.

Even as the Trump administration wades into the exact issues featured in Schilling’s ads, the president has declined to insert himself into recent debates over transgender athletes and transitions for transgender youth. When the Department of Education recently threatened to cut off funding for schools that permit transgender students to participate in sports consistent with their gender identity, the announcement came from the agency itself—not the president’s Twitter feed. And when the Supreme Court sided with LGBTQ workers in Bostock v. Clayton County, shielding gay and transgender workers from employment discrimination on the basis of sex, Trump offered a surprisingly muted reaction given his aggressive criticism of other high court rulings.

“They’ve ruled. I’ve read the decision and some people were surprised, but they’ve ruled and we live with their decision. That’s what it’s all about. … Very powerful decision actually. They have so ruled,” Trump said the afternoon of the Bostock ruling.

It’s not as though these issues have failed to pierce Trump’s information bubble.

One of his preferred Fox News personalities, Tucker Carlson, has mentioned transgender athletes at least 10 times on his show since it first premiered in 2016. In February, Carlson excoriated state legislators in South Dakota for declining to pass a bill that would have made it illegal to administer gender-affirmation treatments, such as puberty-blocking drugs, to children under the age of 16. And Trump’s eldest son, Don Jr., devoted an entire chapter in his debut book Triggered to questioning the fairness of transgender athletes competing in gender-specific sports competitions. The younger Trump later went viral in right-wing circles after a clip emerged of him railing against trans-inclusive sports policies during an on-air interview with CBS.

“When you start saying, ‘I’m a man, I become a woman, I’m now winning national championships, setting weightlifting world records, displacing women who’ve worked their entire lives to get to a point in their careers, I think that’s wrong,” he said, adding as the segment came to a close that he was “interested in winning 2020” for his father.

While many of the president’s allies gleefully retweeted the clip, Trump Jr. never gained a nod from his father for the viral moment.

In fact, as Gillian Branstetter, a spokesperson for the National Women’s Law Center, pointed out to me, Trump’s Twitter log—rife as it is with red-meat comments about abortion, immigration, guns and other wedge issues—includes only one thread about transgender people. “We’re a favorite topic on all his favorite TV shows and his son loves talking about us, but the only time he’s every tweeted about transgender people was when he announced his military ban,” Branstetter said in a phone interview earlier this year. Trump did retweet a story in June from the right-wing media outfit Breitbart about an Idaho lawsuit filed by transgender athletes, though he offered no commentary on the matter.

Even when conservative circles lit up with outrage over the case of a 7-year-old child in Texas whose parents found themselves locked in a bitter custody battle over the mother’s affirmation of the child’s transgender identity (the case involved Luna Younger, who was named James Younger at birth), Trump steered clear of the fervor. Trump Jr. and Sen. Ted Cruz (R-Texas) both likened the episode to “child abuse,” while Texas Gov. Greg Abbott vowed to investigate the matter and Fox News ran multiple segments last October and November about the case across its programming. Still, the president decidedly avoided it.

“It was strange he didn’t weigh into that when it was such an easy layup. There is a growing grassroots energy on this that up until this point is untapped. I would venture to say Americans feel like it’s gone too far,” said one senior White House official, who heard about the Younger case from conservative outside groups at the time.

So why hasn’t Trump sunk his teeth into these issues?

Some, like Schilling, say the president is likely simply waiting for an opportune moment to pounce. “We know [Don] Jr. has pushed these issues and we know donors are paying attention to them, but it’s got to make its way into the mainstream first,” said an official at the Trump-aligned super PAC America First Action, which tested transgender issues in focus groups earlier this year. The group was eyeing the summer Olympics in Tokyo, where three transgender women from the U.S., Brazil and New Zealand had hoped to be among the 11,000 athletes competing, as a potential opening for ads related to trans athletes. But the postponement of the games until next July, well after the election, forced the group to abandon the plan.

Others suppose limitations on what Trump can do to alter trans-inclusive sports policies, or curtail parental rights regarding treatments for transgender children, are the driving factor behind his reluctance to weigh in. “What kind of executive order do you have to deal with this?” said Log Cabin Republicans spokesperson Charles Moran, when I asked for his theory on Trump’s demurrals. “Plus,” he added, “You have to have a really high threshold as a conservative to say, ‘Yes, the government should be allowed to step into this issue.’”

And then there are the conservative agitators and centrist Republicans who both acknowledge the thorny nature of these issues but are diametrically opposed over how the GOP should engage, or even if they should.

“It’s clear Republicans are scared of talking about LGBT issues and the major reason for that is their fear over losing corporate donors. I think it’s going to be a kitchen table issue in the near future, so they should learn to take the risk,” said Joy Pullmann, executive editor at The Federalist, a conservative publication with a roster of media personalities who have earned Trump’s repeated praise.

“Not only is it very risky, it’s really only an issue if it’s an issue for you,” countered a former administration official, arguing that most people who do not know transgender persons won’t relate to a wedge issue involving them. “Until these issues saturate the mainstream, there is no reason the president should be mentioning them on the campaign trail.” As recently as last September, only about 1 in 5 Americans in a Pew Research study said they personally know someone who prefers to use gender-neutral pronouns instead of “he” or “she,” and only 38 percent of Americans in a Public Religion Research Institute survey said transgender individuals face a significant stigma or negative social judgment in their communities.

Even in these vastly different responses, there lies a recurring theme: Just because Trump hasn’t used transgender issues as a wedge yet, that doesn’t mean he won’t ever. Trump is, after all, an opportunistic creature at his core. All it might take is a case as button-pushing as Colin Kaepernick’s protest to incite him.

But if he doesn’t, Schilling knows it will become that much harder to ever campaign on this issue again. In early July, he made a successful fundraising swing through Los Angeles to help bankroll the American Principles Project’s newest ad project, but if it doesn’t produce results soon, he doubts that money will continue to roll in.

“It’s going to be very difficult to make the argument I’m making right now if I end up raising all this money and we still come up short,” he conceded. “I was able to go to donors after Kentucky and say, ‘We came up just short of the goal, but we moved 26,000 voters. Help us use this in 2020 to help Trump.’ But I think you’re right, if we come up short this time it’s going to be difficult.”

Then again, Schilling said, “No fight is ever really lost. We settled the socialism issue in the ’80s and now it’s coming back.”