Every year, Tom Toles’s Halloween party draws an eclectic mix — journalists and political types from Washington’s power elite, but also artists and musicians, everyone from retirees to college kids, jammed into small rooms and sprawled across the backyard, dancing and gossiping, checking out the crowd to see who has the most inventive and outrageous costumes.

At the 2018 party at the home of The Washington Post’s editorial cartoonist, in addition to several Ruth Bader Ginsburgs, someone dressed as the “Mueller Witch Hunt” and Post columnist Dana Milbank came as just-confirmed Supreme Court Justice Brett M. Kavanaugh, complete with a beer-dispensing device on his head. A guest named Lexie Gruber wore a scary “Beetlejuice” get-up and called herself “dead.”

A middle-aged white woman named Sue Schafer wore a conservative business suit and a name tag that said, “Hello, My Name is Megyn Kelly.” Her face was almost entirely blackened with makeup. Kelly, then an NBC morning show host, had just that week caused a stir by defending the use of blackface by white people: “When I was a kid, that was okay, as long as you were dressing up as, like, a character.”

So just before heading over to the party, Schafer, a graphic designer and friend of Toles, decided to dress as Kelly in blackface to mock her, she said.

Some of the approximately 100 guests at the home of the cartoonist in the District’s American University Park neighborhood said they didn’t notice the blackface. Some noticed it and said nothing. A few people walked up to Schafer, who was then 54, and challenged her about her costume. Gruber, who is of Puerto Rican descent, and her friend Lyric Prince, who is African American, confronted Schafer directly.

“You understand how offensive that could be to a person of color?” Gruber said, according to two witnesses.

“I’m Megyn Kelly — it’s funny!” Schafer replied, the witnesses said.

Nearly two years later, the incident, which has bothered some people ever since but which many guests remember only barely or not at all, has resurfaced in the nationwide reckoning over race after George Floyd, an unarmed African American man, was killed when a white police officer in Minneapolis knelt on his neck for nearly nine minutes. Many protesters have called on white Americans to reassess their own actions or inactions when confronting violent and everyday racism alike.

Gruber felt compelled to revive the 2018 incident. Last week, she emailed Toles, whom she has never met.

“In 2018, I attended a Halloween party at your home,” she wrote. “I understand that you are not responsible for the behavior of your guests, but at the party, a woman was in Blackface. She harassed me and my friend — the only two women of color — and it was clear she made her ‘costume’ with racist intent.”

Gruber, a 27-year-old management consultant, told Toles that the incident had “weighed heavily on my heart — it was abhorrent and egregious.” She asked him to help her identify the woman.

“After the killing of George Floyd and the protests, I began reflecting more on this incident,” Gruber said in an email seeking Post coverage of the incident.

“I wanted to know who this woman is. . . . What impact does she have on society? I think this is an important story — that a party full of prominent people in Washington welcomed a person in blackface, danced and drank with her, and watched in silence as she harassed two young women of color.”

Prince, 36, a science writer, art critic and artist, wants Schafer to explain publicly why she did what she did. “I don’t want an apology because that time has long passed,” she said. And she wants Toles to make it clear publicly “that what [Schafer] did was wrong and that . . . that’s not the kind of person that he knows to be a good person.” Perhaps most of all, she said, “I want people who read this story to say to themselves, ‘I cannot excuse my friend’s bad behavior because it does reflect on me if I say nothing.’ ”

Looking back, some guests at the party say they wish they had confronted Schafer more aggressively. Others say that she has already paid a price and that her embarrassment and regret were evident when she left the party in tears.

“I wish I’d have been the one to call her out,” said Philippa Hughes, a Washington arts entrepreneur who attended the party. Hughes, who is Asian American, is friendly with both Gruber and Schafer. “I did go up to Sue and say, ‘What the hell?’ But it took Lexie yelling at her to make her leave.”

Despite her certainty that wearing blackface was wrong even as a satire aimed at Kelly’s embrace of a racist gesture, Hughes is torn about whether the incident should be reopened.

“When it becomes public, it will be too much of a punishment,” she said. “It’s unfair to go back and attack some clueless woman, because she’s not a public person and she was punished then — by Lexie, by people who chastised her afterward, by Tom. But on the other hand, people do need to be held up as an example of the lines we’re going to draw about what’s acceptable behavior. Every single person at that party should have said something to her. There’s culpability all around.”

'No one would ever do that'

Toles, a 68-year-old Pulitzer Prize winner whose cartoons playfully and often bitingly express a decidedly liberal perspective, replied to Gruber’s email last week with “apologies for your experience at the party. A lot of people show up who I don’t know, and I don’t recognize the woman you’re inquiring about.”

Toles did not tell Gruber who had worn blackface.

But Toles did know Schafer, who had been to his parties before and is a friend of his family.

When he denied to Gruber that he recognized Schafer, Toles said in an interview Sunday night, “I meant that I didn’t recognize any bad intent. I didn’t feel it was my place to tell her who my other guest was when she had misinterpreted what the other guest intended” with her costume.

Toles said in the interview that he had confronted Schafer at the party and again later.

“She explained to me very quickly when she came in that she was trying to show what a jerk Megyn Kelly was,” Toles recalled. “I told her this was an ill-considered attempt at satire. She went on and on about what a horror it was to find something to use [as] blackface. She told me that in the cab on the way over, with a black cabdriver, he was upset, and then she explained what her costume was and then he wasn’t upset.”

Later in the interview, Toles said he was not certain that he had told Schafer at the party what he thought of her costume. “I may have told her that wearing blackface wasn’t appropriate, but I’m not sure I did,” he said, “and maybe I should have. . . . I could have told her to leave. I didn’t and that’s on me. Maybe I should have.”

Toles’s boss, Post Editorial Page Editor Fred Hiatt, said: “Blackface is abhorrent, period. I know Tom feels the same way, I know he wishes he had made that clearer to the person who came to his party wearing an offensive costume, and I’m glad he has apologized.” The Post’s editorial and opinion pages are administered through a separate chain of command from the paper’s news operation, which is run by Executive Editor Martin Baron.

In addition to Toles and his wife, Gretchen, another couple, Steve Rochlin and Christina Sevilla, co-hosted the Halloween party. Rochlin, a consultant on environmental sustainability, said that when he saw Schafer, “my reaction was, ‘What the hell?’ I asked why she was in that costume and she explained she was being Megyn Kelly.”

Rochlin said he told Schafer, “ ‘Whatever you’re trying to do, it’s offensive.’ And I said, ‘I’d like you to wash that off or go.’ She looked stricken, almost starting to tear up. Shortly after I spoke to her, she left.”

Earlier that evening, as they got ready for the party, Gruber and Prince had talked about the Kelly controversy and about what might happen if someone showed up in blackface.

They agreed that “no one would ever do that,” Gruber recalled in an interview.

But about 15 minutes after Gruber got to the party, she saw Schafer in blackface in Toles’s backyard. “I thought there’s just no way,” Gruber recalled. “I had never seen someone in blackface before. . . . It was like, ‘Holy s---, this is for real.’ ”

Benjamin Ross, a video company executive who attended the party as a friend of Gruber, Prince and another woman, said: “We had a record-scratch kind of moment, like, is there a frigging woman in blackface here?”

Gruber said that she and Prince were among only a handful of people of color at the party, and that most of the guests were considerably older. “Lyric and I felt very out of place,” she said.

She resolved to remain quiet about the woman: “I said, ‘I’m not going to say anything. I’m not going to ruin my night.’ ”

But then Gruber and her friends moved inside, got drinks and found themselves in the crowded living room. Prince, who is 6-foot-1, easily spotted the woman in blackface and pointed her out to Gruber. “What should we do?” Prince said.

She approached Schafer. Prince said she criticized Schafer’s makeup and told her, “You look horrible” — a way of “clapping back” at the blackface without addressing race head-on. Prince said in an interview that she was worried about being stereotyped as an “angry black woman,” worried that someone might call the police.

“I felt very unsafe talking to that person in the first place,” she said. “I was in an environment that, if it got heated, it would decidedly not be in my best interest.”

Another guest, who spoke on the condition of anonymity to protect friendships, said Schafer laughed after Prince said her makeup was “very ugly.”

Gruber also said that “the woman basically just started laughing.”

Schafer agreed that she laughed but said that it was a nervous laugh, a sign of extreme discomfort, and that it came “only when she told me that I was ugly and had wrinkles. She told me, ‘You think you’re so meta,’ and I didn’t say anything. I didn’t argue with her.”

Prince said of Schafer: “She looked very proud of herself, as if she was eliciting the kind of response that she had been hoping for.”

Prince viewed the blackface not as a satire aimed at Kelly, but rather as the opposite — as “a mockery of the outrage that Megyn Kelly produced. I find it very hard to believe that a white person does not know blackface is offensive. . . . That was the whole point of blackface to begin with — to mock black people.”

After Prince confronted Schafer, Gruber felt that she had to say something more direct.

Gruber asked Schafer whether she knew the history of blackface. “People have been murdered,” she recalled saying. She said she addressed Schafer “calmly and politely.” “They lynched people back in the day. There’s a painful history, and you should have some respect for that.”

Ross, who is white and was standing next to the women, said Gruber’s methodical explanation of the immorality of blackface “was beautiful, very respectful. And the woman just laughed at Lexie, very denigrating and flippant. She was not at all apologetic.”

Three witnesses described Gruber as “yelling” at Schafer, and Gruber said that “there wasn’t a single person in that party who didn’t hear me when I spoke.”

Gruber and her friends left the party immediately after the confrontation.

“This was a roomful of elite somebodies, and nobody wanted to touch this,” Ross said. “Nobody asked the woman to take off the costume. She wasn’t asked to leave. There was just silence. We felt like we had to leave.”

Gruber said she burst into tears as soon as she left Toles’s house.

Prince said, “I was pretty much just in a state of, like, shock.”

Schafer said that after the confrontation, she walked into the next room, “tried dancing and it just didn’t feel right, so I left.” She didn’t want a cabdriver to see her in blackface, so she had her cousin, who was at the party, drive her home.

'I'm deeply ashamed'

Schafer said she realized from the moment she entered Toles’s house that she’d made a terrible mistake.

The next day, she called Toles with “absolute remorse about the costume . . . extremely upset on reflection, and apologetic,” Toles said. “She did not come with the intent to confront, embarrass, ridicule or insult anybody.”

Toles said Sunday night that he feels “terrible that [Gruber] had such a bad experience. But I know [Schafer] felt so terrible that I don’t feel comfortable dragging [her] into a public situation that will misrepresent what she was doing.”

On her Facebook page, Schafer posts often about her opposition to President Trump and her support of immigrants, gun control, gay rights and anti-racism causes, including photos she took at marches and demonstrations she attended.

Schafer said she has spent many hours in therapy talking about “how carelessly I behaved. I’m deeply ashamed.”

Prince, too, has sought to work through the events of the evening with a therapist. “It was a humiliating experience for me,” she said. “I felt threatened and physically and emotionally exposed. . . . I felt powerless in a way that I never want to feel again.”

Schafer said she has learned in recent weeks, as protests have sparked new conversations about race, that racism “runs so much more deeply than I’d thought. I should know. I’m Jewish and my grandmother was a child slave for two years. I’ve hung my head for months. I hurt people in my carelessness.” She said she understands Gruber and Prince’s “pain and their consternation and their hurt. Clearly, I didn’t understand the history of blackface enough. I failed completely, but I’m not a malicious person.”

Schafer wrote an email to Tom and Gretchen Toles the day after the party, saying that she had “made a huge mistake. I’m very sorry I ruined the evening for some of your guests.”

She said she would like a chance to tell Gruber in person how sorry she is: “With this story, they’ll get the public humiliation they want, but it won’t foster any real dialogue between us. I wish they would talk to me. I made a mistake, and I understand now that when black people make a mistake, they can get killed.”

On Wednesday, after Schafer informed her employer, a government contractor, about the blackface incident and The Post’s forthcoming article, she was fired, she said.

'A hard line that you never cross'

Everyone involved in the incident agrees that the message blackface sends is unmistakable.

“Blackface is a hard line that you never cross,” said Hughes, the artist, who wrote a blog post about the incident a few days after the party without naming anyone. “I can super-intellectualize it to argue that what [Schafer] did was satire, it’s a commentary, but emotionally, I mean — I get the joke, but it’s not funny.”

Hughes said the incident “reminded me how tough and complex it is to talk about race, now more than ever. I try to have compassion for when people make mistakes like this, particularly because I know I will make mistakes. And these days, there’s so much calling out and canceling that I am worried that progressives are actually making it harder to achieve the policy goals we want. On the other hand, I think there are lines we need to draw, and wearing blackface in 2018 under any circumstances should probably be one of them.”

This week, Gruber and Toles traded emails. The exchange started out promisingly.

“I understand that you are not responsible for the behavior of your guests,” Gruber wrote.

Toles replied that he was “wrong” to deny that he knew who was wearing blackface. “I am sorry — for that, and more,” he wrote. He admitted that Schafer was “a friend.” He said he has realized that wearing blackface “was offensive in any context. I regret I did not see that more clearly at the time, and I apologize to you now unreservedly for that.”

But Toles did not give Gruber the woman’s name, and Gruber reacted sharply: “Hiding her name is a deliberate act of white privilege and cowardice, not friendship.”

In response, Toles offered to connect Gruber with Schafer, who he said wanted “a chance to explain and apologize to you herself.”

Gruber replied that she has “a hard time believing that you are genuine in remorse. . . . I do not feel comfortable reaching out to a woman who publicly harassed me and my friend — simply because we are not white. This happened in public — and so I want a public apology, not a private one.”

She told Toles that he was not innocent in the conflict: “As you well know,” Gruber wrote, “we are an extension of the company we keep.”

An earlier version of this story slightly mischaracterized Prince’s profession. She is a science writer, art critic and artist.