Renee Ferguson, a prominent black television journalist in Chicago, arrived outside the swanky office building with a videographer and her intern — a Harvard sophomore named Peter Buttigieg.

In the summer of 2002, Ferguson had been reporting on an investigation about a sex offender working at a day care in the building’s basement. The three wanted to capture undercover footage of the man on the job.

But when Ferguson tried to get into the building, a security guard turned her away. The videographer, who was also black, tried next. The security guard turned her away, too.

Then, Buttigieg gave it a shot. When he approached the door, the security guard let him in. Buttigieg secured footage that would help Ferguson win one of her seven Emmys, but what stayed with her most was the prejudice that she figured led the young, white intern to acquire access that two black reporters could not.

“I think I understand what white privilege looks like,” Ferguson recalled telling Buttigieg.

“I don’t know if that’s what’s going on,” he said.

“Yes, you do know,” she said. “I couldn’t get in, but you could. Think about how many times in your life that you’ve just been able to walk through doors and the rest of us got turned away.”

Seventeen years later, Pete Buttigieg is still thinking. As a presidential candidate who has rocketed to the top tier of the Democratic primary field, he is scrambling to address what has emerged as a glaring deficiency: his inability to connect with black communities.

Just off a tour of black churches, colleges and neighborhoods in the South, he has tried to introduce himself to voters who, as he has said repeatedly, “might not yet know me.”

But the issue is not simply a matter of whether the black community knows him. He is battling doubts that he knows the black community well enough to be the Democratic nominee.

As a white man with a privileged background who has fumbled relationships with minorities as mayor of South Bend, Ind., the 37-year-old Buttigieg has long been on a quest to grasp the African American experience — and his relationship to it. The journey began even before running for office, as a college student, an intern, a young adult trying to make sense of his heritage and his sexual orientation.

Friends and colleagues describe him as a man still forming a sensibility about African American issues and culture, a work-in-progress.

When confronted about the subject in South Bend, even Buttigieg’s critics there concede he can be well-intentioned and thoughtful. He listens. Nonetheless, they found themselves surprised and frustrated by a streak of attempts to assure black voters that have come off as clumsy, at best.

In his first appearance last summer in a nationally televised presidential debate, days after a white police officer who didn’t turn on his body camera shot a black man in South Bend, Buttigieg admitted that he was unable to figure out how to diversify his city’s police force.

“I couldn’t get it done,” he said.

His campaign angered some African American leaders in South Carolina after at least one was listed as endorsing Buttigieg’s agenda for the black community when they had not. Making matters worse, his campaign issued a photo promoting that agenda featuring a black mother and child who live in Kenya, not the United States.

Just this month, Buttigieg shocked some of his own residents when he said that in South Bend, his racially stratified hometown, he had “worked for years under the illusion that our schools in my city were integrated.”

“It sounded like he wasn’t even from here,” said Henry Davis, Jr., a city council member who ran against Buttigieg for mayor in 2015. Davis wondered how a man who was so intellectually curious that he learned Norwegian to better understand a novel, who went out of his way to learn an Aboriginal wooden instrument called the didgeridoo, could be so unaware about segregation patterns in his own city.

“I think it’s irresponsible for him to not know, when trying to assume such a prominent leadership role,” Davis said. “By admitting his ignorance and still expecting to serve at such a high level, he is just playing into his own white privilege.”

Buttigieg tried to play down such criticisms.

“I think that’s an uncharitable interpretation of the humility that I try to express, knowing how big a mistake it would be to pretend that I understand African American culture or life any better than I do,” Buttigieg told The Washington Post in an interview.

“A part of this is negotiating differences,” Buttigieg said. “I guess there’s two ways to do it. One is to make a show of how much you think you understand. The other is to lay out how much you know that you might not know and put it out there. And some folks will, hopefully, view that as an invitation to continue the dialogue.”

'Feeling a little different'

That dialogue started in earnest during the summer of 2002, when he interned at the Chicago television station with Ferguson.

Although Buttigieg said his memory of the undercover pictures was “fuzzy,” he said his relationship with the journalist was eye-opening in terms of understanding race and racism in America.

“My best chances, especially growing up, of understanding the black experience were through literature,” Buttigieg said. “I mean, I knew some number of black folks in my life, but until Renee — not a lot that we could talk about race.”

The two had first met earlier that winter, when Ferguson was on Harvard’s campus to receive a journalism award. A professor told her there was a student he really wanted her to meet, Ferguson recalled.

“He wants to be president one day,” she recalled the professor saying.“But he wants to understand how the media works.”

Buttigieg was interested in doing an internship at her television station. Ferguson had no plans to advocate for him. She liked him, but as an advocate for diversity, she was pushing for her station to find an African American intern — or at the very least, someone who actually wanted to be a reporter.

Buttigieg’s application essay was so persuasive that he got the spot anyway. He showed up to her office on his first day at work suitcases in hand. His housing plans had fallen through, and Buttigieg, a 20-year-old who had never been to Chicago, planned on improvising until he found something more permanent.

Ferguson, fearing this oblivious young intern would make an unwise choice, offered him a room in her house — much to the confusion of her husband and her cocker spaniel, Goldie, who bit Buttigieg on the first meeting.

“He was going to stay at the Y!” Ferguson recalled telling her late husband, Ken Smikle, also a journalist. Smikle stopped his protestations; any student who thought staying there was a good idea surely needed help.

That summer, Buttigieg became an adopted member of a black family living in Hyde Park. He ate dinner with them, helped Ferguson’s son with his math homework and eventually gained enough trust from Goldie that she allowed him to walk her.

On the job, Buttigieg was interviewing black men who had been assaulted by police and forced into false confessions. He made the connection between that and the advice Ferguson’s husband told their son when he was grumpy one morning: Start the day with gratitude that you are alive.

Ferguson said she told him about her childhood, growing up in a palatial home in Oklahoma, where black travelers stayed overnight because there were no hotels around serving them. She talked about her father spending nights on the front porch with a shotgun in hand; outsiders were throwing rocks at the property after he registered African Americans to vote.

Before then, Buttigieg said he thought “racism was about these big epic clashes that you read about in school.” But Ferguson’s experience “helped me to understand what it’s like when these problems leap off the page,” he said.

Growing up, Buttigieg had related to African Americans through novels such as Ralph Ellison’s “Invisible Man” and Toni Morrison’s “The Bluest Eye,” a seminal work that explored the inner-tumult of a black girl who wanted white features in a world that didn’t appreciate her beauty. Buttigieg saw himself in Pecola Breedlove, the book’s main character. As the son of a Maltese immigrant with a funny name and a young man struggling with his sexual orientation, he, too, felt like an outsider.

“I was trying to figure out how to conform to the environment around me because I was always feeling a little different, a little off from the norm,” said Buttigieg, who publicly announced he was gay in 2015. “Maybe just because I was from a family that was a little different, maybe because I was beginning to understand that I was different.”

Ferguson recalled that telling Buttigieg he was privileged was “quite disturbing for him.” It was hard for him to reconcile the feelings of being an outsider that he had of himself with the reality that he might be receiving benefits that others might not.

“He got very emotional,” recalled Ferguson, who is supporting his presidential bid.

“Don’t get emotional,” she told him. “Do something about it. And he did.”

'Everyday nature of racism'

The lessons he learned in Chicago did not seem consistent with the messages he picked up at Harvard, where he said “the university wanted us to feel like we’re in an environment where racial challenges were not present.”

But it was becoming clearer to him that those ideas were pushed mostly by the white people in his life. When he asked his minority friends if they thought the country was becoming colorblind, their answer was resoundingly no.

Buttigieg said he saw their reality up close one summer when he visited his roommate, Uzodinma Iweala, a Ni­ger­ian American who lived in the wealthy, mostly white Washington suburb of Potomac, Md. In one day, Buttigieg kept seeing what he called “racial bullshit.”

He recalled someone stopping Iweala to ask if he lived in the neighborhood — while presuming that Buttigieg did. Hours later, they went to a party at the house of Iweala’s friend, who was also black. A white person asked Iweala if he and his friend were related, even though they looked nothing alike.

Buttigieg said the experience showed him how exhausting the “everyday nature of racism” must be.

“If all you have of race and race issues is kind of a history lesson, then you think, as long as you’re not doing anything knowingly racist, everything will be fine,” Buttigieg said. “But of course, the reality is that there’s a lot more to it.”

The knowledge made a big impact on Buttigieg. He became self-conscious. He didn’t want to be the white person who was burdening black people.

“The more conscious I became, the more I felt I needed to be intentional,” he said. “I don’t think it was always obvious to me what that meant.”

When Buttigieg and Iweala got back to college, they said, they became preoccupied with two questions: What makes an identity? And how do you speak to identities that are different?

Buttigieg and Iweala agreed that bridging differences would be a matter of listening, asking good questions and having a welcoming attitude.

In the efforts to create those experiences, Buttigieg tried to make their dorm rooms feel homey over their years living together. They christened their place “The Chateau.” Buttigieg would order smoked salmon for his roommates, put up a Christmas tree and make eggnog, with Buttigieg occasionally holding a pipe akin to the host of “Masterpiece Theater.”

“We had a feeling that we wanted to essentially create a space where all are welcome, no matter where you may come from — be it a Nigerian American from D.C., a Maltese American from Indiana, a Lebanese American from Massachusetts, a Chinese American from California; that finding a common place would bring us all together,” said Iweala, 37, now an acclaimed author and executive director of the Africa Center in New York.

But his friends noticed Buttigieg wasn’t just interested in the interpersonal nature of these discussions. He began asking another question: “How does difference impact experiences and participation in politics?”

Answering that question became even more necessary eight years later when Buttigieg, at 29, became mayor of South Bend, a city that is 26 percent black.

For a community trying to suss out the intentions of a young mayor who attended wealthy, white private schools, Buttigieg’s opening acts offered little comfort that he got them.

Within months, he fired the city’s first black police chief. He levied hefty fees on property owners of blighted homes in minority neighborhoods, threatening to knock them down to beautify the city.

He even had to be talked out of being inaugurated at noon on New Year’s Day, when many of his black residents would still be in church.

“Who doesn’t know that?” said Oliver Davis, a city council member.

Buttigieg tried to assure black residents that these moves were not racially motivated, which left some flabbergasted. Aggravated, a young black activist asked him over coffee, “Do you think we live in a colorblind society?”

“Of course not,” Buttigieg said he responded.

If that was the case, they wanted him to show it.

Regina Williams-Preston, who fought against the debt-inducing fees she carried after she and her husband bought two fixer-uppers right before Buttigieg’s blight campaign, found Buttigieg too quick to consult data and research papers than the lived experiences of his black constituents.

But she admired how much he tried. He’d take activists out to coffee. During meetings, his staff said Buttigieg began to look out for African Americans making disapproving faces, or raising eyebrows when he was making a point. It happened so frequently that Buttigieg said he started to pull them aside afterward to ask more questions.

His frosty relationship with the black community started to thaw. Williams-Preston would eventually end up on the city council and appreciating his decision to start an office of diversity and inclusion in 2016 so he could address his shortcomings.

As a former diversity trainer herself, Williams-Preston found that Buttigieg was not “very different from many white men who are doing the best as they go.”

“When it comes to Pete, I know there’s a lot of a backlash and truly he’s made a lot of mistakes,” she said. “But the real issue is not Pete; the issue is the worldview through which [his] decisions were being made. And I would say, one thing, as a credit to this leadership, he’s at least been able to listen.”

Williams-Preston is undecided about whether Buttigieg should be president, but she said watching this journey would be a good lesson for future white politicians who have diverse constituents.

“It’s a good opportunity for the country to see what he is going to do,” Williams-Preston said. “How can he change and adapt? He’s young and he’s been on a very steep trajectory, so maybe he’s missed a lot because he’s been on that trajectory. But it’s exciting to see that he’s on a path.”

Buttigieg would end up hiring a program manager from the University of Notre Dame named Christina Brooks to lead the diversity office. In their time working together, she said she found at least one surefire way to persuade him.

During a meeting over whether the city should commission a study looking at racial disparities in the distribution of city contracts, she reminded the group that the city had first promised to do the study in 1987.

“The community has been waiting for the results,” Brooks recalled saying. “It would be great if we could deliver on that promise.”

With the loom of an unfulfilled promise hanging over the black community for a generation — and also a potential presidential campaign — Buttigieg approved the study.

A curious intellect

Buttigieg is still asking how to deal with addressing differences.

He brought it up with the Rev. Al Sharpton when they dined at a soul food restaurant in Harlem. Sharpton noticed that Buttigieg was “very self-conscious in that he did not want to rub people the wrong way or be misunderstood,” so much so that he asked Sharpton if it was okay to eat fried chicken with his hands.

Buttigieg primarily wanted to know whether Sharpton thought African Americans would accept his difference, being a gay candidate, Sharpton said. Sharpton told him to “be candid and say, I am how I am, and be nonapologetic and not be arrogant. You’ve got to talk to them like you understand their reality rather than this preconceived notion.”

Other politicians were able to overcome differences — and form strong connections with the black community. Bill Clinton demonstrated such a comfort and knowledge of black culture that Morrison, the author, referred to him as “the first black president.” Barack Obama, who at first received questions about whether his Kenyan ancestry made him “black enough” for African Americans, drew appeal through his charisma and the history-making nature of his presidential candidacy.

In many ways, Buttigieg’s struggle contrasts with another front-runner who is trying to appeal to moderates, former vice president Joe Biden. Biden’s racial lens was largely based on forming relationships, which have endeared him to black voters in South Carolina even as a young generation harps on his lack of familiarity in discussing systemic racism.

Buttigieg, meanwhile, has been criticized for understanding race on an academic level, but not on a personal one. It’s the difference in their approaches in their formative years. When Biden wanted to learn about black culture, he took himself to the local pool. Buttigieg went to the bookshelf.

Sharpton suggested Buttigieg lean into his personality as a curious intellect.

“The fact that he wants to learn what he does not know and represent it as part of his campaign and his quest of the presidency, with having the Ivy League kind of background, is a good thing,” Sharpton said. “I think if we tell people you have to stop engaging in classism and racism and gender bias and homophobia, [we can’t be] biased against people who are well-educated and veterans and kind of nerdy-like.”

Buttigieg’s political opponents argue that the polarizing times call for a president who can lead on race issues, not just learn about them.

And then there’s the issue of how he has represented what he has learned. When he suggested during a debate last month that being gay helps him empathize with African Americans familiar with “feeling like a stranger in my own country,” he was channeling the emotions he experienced with his roommate while walking through Potomac, his empathy with main character in “The Bluest Eye.”

But Sen. Kamala D. Harris (D-Calif.), who has since ended her presidential bid, dismissed his rhetoric as “a bit naive.” Some worried he might revive a tension between the black rights and gay rights movements.

Oliver Davis, a South Bend council member who has since endorsed Biden, groaned when Buttigieg made that allusion. It has felt to him like Buttigieg was showing the same tone-deaf nature he had when he first became mayor. When Buttigieg’s campaign first started, something happened that made the council member question whether his mayor had truly learned anything at all.

Buttigieg announced his candidacy in South Bend at an old Studebaker plant. The crowd was overwhelmingly white. Many older black residents, Davis said, would not attend even if they were interested. It started at noon on a Sunday, and they were in church.

Correction: An earlier version of this article stated the wrong time for Pete Buttigieg’s event in which he announced he was running for president. The article also incorrectly said Barack Obama spent his youth in Kansas.