This story was co-published with Glamour.

If you spend any time on Facebook or Twitter, you may have seen one of the Lincoln Project’s viral ads. Or the president’s responses to them.

The day after President Donald Trump returned to the campaign trail in Oklahoma last month after a coronavirus-induced hiatus, the group founded by anti-Trump Republican operatives released a video about the Tulsa rally called “Shrinking.”

“You’ve probably heard this before but it was smaller than we expected,” a female narrator says as the president holds up his hands. “It sure wasn’t as big as you promised.”

In an earlier ad about Trump campaign manager Brad Parscale, the group suggests he has gotten rich at the president’s expense. A female narrator details Parscale’s yacht, Ferrari, and Florida estates while illustrating his alleged high-flying life with images of women partying on a boat in skimpy bikinis and smacking their own buttocks.

The Lincoln Project’s ads have gotten Trump’s attention. He has blasted the group in late-night Twitter tirades as a “disgrace” and its founders as “losers.” The media can’t get enough of the group, describing it as a potentially disruptive force that can expertly troll the president with “potent ads” that a New York Times op-ed writer recently described as “miniature operas of contempt.” Donors have also taken notice, helping the group raise $16.8 million in the last quarter.

Lincoln Project cofounder Rick Wilson reiterated during the group’s first virtual town hall last week that their ads are not just about trolling the president. The group wants to “litigate the case against Donald Trump.” They intend to spend 85 cents of every dollar on voter contact, he said. The group’s latest fundraising filing due Wednesday is being closely watched after earlier questions about how the project is using its money.

As the group expands and its leaders make the rounds on cable news programs, no one is talking about how The Lincoln Project plans to target the group of voters most open to changing their mind about the president: women.

Polls show that women, specifically suburban and White women without college degrees, are souring on the president at higher rates than their male counterparts, making them a must-reach demographic. As many as half of White women backed Trump in 2016.

The Lincoln Project declined repeated requests to discuss whether and how they planned to reach out to women voters, though winning them over would be essential to its stated goal of making Trump a one-term president.

A potential pitfall in that project is the group’s style, which emphasizes masculine leadership attributes while strategically deploying female narration to mock Trump’s stamina, sexual prowess, and mental acuity. These tactics are unlikely to appeal to these women and could even turn some off, according to a dozen political strategists and messaging experts familiar with their ads and the female electorate.

“These are not ads that are targeted at the lower-hanging fruit,” says Anat Shenker-Osorio, a language researcher and progressive communications consultant, referring to winnable women voters.

“If you want women on board, you’re going to have to produce content that speaks to women,” she said.

“The dominance of White men among political practitioners influences how we run campaigns,” says Kelly Dittmar, a political science professor and scholar at the Center for American Women and Politics at the Rutgers Eagleton Institute of Politics.

Seven of the Lincoln Project’s eight cofounders are men: George Conway, Reed Galen, Mike Madrid, Ron Steslow, Steve Schmidt, John Weaver, and Wilson. Many worked for George W. Bush, his father George H.W. Bush or Senator John McCain.

Cofounder Jennifer Horn, the former head of the Republican Party in New Hampshire, is frequently not as looped in to high-level strategy discussions as her male counterparts are, according to individuals familiar with the group’s inner workings. Half of the Lincoln Project’s 10 senior advisers are women, but senior advisers do not play a large role in the group’s day-to-day activities and messaging.

Wilson is the group’s creative director. Until this week many of its most-watched ads were created by Ben Howe, a video editor who came of age politically making anti-Obama spots during the rise of the Tea Party. Howe was dismissed late Monday for Twitter posts in which he used female anatomy as an insult, calling rivals a “vagina” or “c-nt” or “twat.”

On the same day Howe parted ways with the Lincoln Project over what its spokesman called his “unacceptable and offensive posts,” Wilson said during a segment on CBS’s Tooning Out the News, an animated satire show produced by Stephen Colbert, that Trump is a “whining bitch addicted to Twitter.”

“Yes, he is a bitch. That is the biggest insult, comparing someone to a woman—I hate us,” responds cartoon anchor Sarah Sabo, voiced by Maureen Monahan.

Monahan points out in the same segment that Wilson previously called attendees of the liberal Netroots Nation conference “Barack Obama’s bitch” and “pathetic little whores satisfied with crumbs and head pats.” Ahead of the 2016 election, Wilson asked conservative commentator Ann Coulter on Twitter if Trump paid her “more for anal,” insinuating she was prostitute as an insult.

The Lincoln Project also declined requests to respond to Wilson’s statements.

When photos of Wilson with a Confederate flag cooler with the words “The South Will Rise Again” resurfaced last month shortly after the Lincoln Project released the ad “Flag of Treason,” the group did not release a statement or otherwise address it.

“I thought it was hypocritical for the Lincoln Project, in the middle of George Floyd and Blacks Lives Matter protests, while running ads blasting the president as a racist, to be loudly silent when one of their senior guys was caught with pictures of a Confederate-flag cooler right behind his head on a boat,” says Sophia Nelson, a Black woman who was a senior adviser to the Lincoln Project and former counsel to a Republican congressional committee. “At the very least there should have been a statement from the Lincoln Project saying, ‘We do not support confederate symbols and we respect Black people and Black lives.’”

Nelson herself was dismissed by the Lincoln Project earlier this year for using the word retarded to describe the president on Twitter though she removed her post and apologized. She says she does not think Wilson should be “canceled” as she was but “there has to be a reckoning” for conservative White men on race as well as gender.

As Melissa Payton, a liberal voter in Oregon, puts it: “I feel like I know them—smart, wise-ass, affluent conservatives who grew up in a less enlightened time and haven’t shed their bro-ness despite being anti-Trump warriors.”

“I have been put off by the sexy whispers, bodacious female bodies, and close-ups of glossy red-lipsticked lips,” she says.

She was referencing the Lincoln Project’s ad about Trump campaign manager Parscale and another called “Whispers,” which suggests the president’s inner circle is gossiping about him. The female narrator says they talk about how he’s “mentally and physically weak” and “laugh when you can’t walk down a ramp or drink water.”

Not all of the group’s ads utilize sexual innuendos and make overt references to Trump’s manhood. Others feature speeches by past U.S. presidents and criticize Trump’s coronavirus response. Still, the ads heavily emphasize almost exclusively male leaders and traditionally masculine qualities, experts say.

Dittmar says that using a masculine strategy made sense for Trump in 2016, when more than half of Americans and more than two thirds of his primary supports said they feared “society was becoming too soft and feminine.” His team tapped into this to “reassure voters of a return to an earlier era in which manhood, at least for some men, felt less precarious,” she wrote in a recent analysis.

Dittmar questioned, though, whether the strategy would work for Trump’s opponents. Voters having second thoughts about the president likely already see him as an ineffective leader and “I think the masculinized ads risk turning off some folks,” she said.

Trump won support from between 47% to 52% of White women in 2016, according to exit polls and post-election analysis, and persuading voters to abandon him will require outreach to women, specifically the suburban women who led to the Democratic takeover of the House of Representatives in 2018 and to White women without college degrees.

The Washington Post recently reported that an “already historic partisan gender gap” is taking shape. Democrat Joe Biden recently held a 23-point lead over Trump with women overall; Hillary Clinton won them by 14 points in 2016. Among women without college degrees, Trump still holds an advantage, but it is dwindling.

Trump’s reelection campaign knows that critical to its mission are suburban and White, working-class women, who are souring on the president at higher rates than their husbands, fathers, brothers, and sons. The Republican National Committee considers them a key demographic among the “downshifters”—voters who backed Trump in 2016 but supported Democrats in 2018 or did not vote—they hope to win back this year.

Biden pollster Celinda Lake, who specializes in the female electorate, says for success in November: “We don’t even have to win these women. We just have to make sure we lose them by less.”

Women are less likely than men to find negative ads compelling, and there is risk in pursuing that strategy if you truly want to reach potential swing votes at a time when many female voters cite Trump’s divisiveness as a top concern, experts say.

Shenker-Osorio has said the messaging road map if you want to defeat Trump looks like this: (1) make ads that target women, not men, because they are more open; (2) use “uniqueness, humor, surprise” as most voters, and in particular swing voters, turn off political ads in fewer than four seconds; and (3) create a “permission architecture” for a person to contend with “having been wrong” and to change their mind because simply attacking Trump makes them “feel you’re impugning them.”

Katie Drapcho, director of polling and research at Democratic group Priorities USA, says: “Women make up a big percentage of our persuasion universe and they’re driving the messaging we are focusing on.”

Drapcho says the group’s polling in battleground states shows that suburban women and White women without college degrees are moving away from Trump, and “it’s absolutely imperative that we be communicating with them.”

“One of the things we’ve found over and over again is that highlighting the ways in which his administration and its policies have harmed families is the crux of a successful persuasion campaign,” she says.

When elections become a contest about which candidate is the manliest, there can be a bigger-picture fallout for women that extends beyond one election, according to Dittmar.

The recent Biden ad “That’s a President” shows the former vice president with nearly all male and military leaders as various presidential attributes flash across the screen. (Once they get to the attribute of “compassion,” a few women appear.) It was described by male political reporters as “very MAN” and likened to a Ford F150 truck commercial.

Even mask wearing has become a political battle over masculinity. Over the weekend, after Trump wore a mask for the first time during a visit to Walter Reed National Military Medical Center, his supporters praised him for doing so in masculine terms.

The display “reaffirmed that his folks are very comfortable engaging in a contest over who is manliest,” Dittmar says.

“If the playbook for over 100 years has been for a presidential candidate to prove he’s man enough for the job and therefore emasculate his opponents, the battle is over masculinity,” she says. “Your engaging in a strategy of emasculation only reinforces masculine dominance and doesn’t envision a world or a presidency in which you could value other traits or areas of expertise as important.”