SOUTH BEND, Ind. — Pete Buttigieg had been mayor just 13 weeks when he faced a leadership crisis.
It was March 2012, and 300 residents of South Bend, Ind., solemnly marched to the Martin Luther King Center to protest the killing in Florida of a black teenager, Trayvon Martin.
A prominent figure at the demonstration was Darryl Boykins, South Bend’s first black police chief. Admired for teaching tennis and boxing to young people, he had been promoted to chief five years earlier after winning the respect of both black and white officers in a department that sometimes divided along racial lines.
Mr. Buttigieg addressed the protesters, but seemed not to interact with Mr. Boykins. What no one in the crowd knew was that the police top brass were in turmoil — shaken by allegations that Mr. Boykins had improperly taped phone calls of senior white officers who were said to have used racist language, including about him.
With federal prosecutors scrutinizing Mr. Boykins, the 29-year-old mayor fired the veteran police chief just before the Trayvon Martin protest. No action was taken against the officers. Precisely what they said on the tapes of their department phone calls is unknown to the public: Mr. Buttigieg has refused to release them, saying the matter is still being resolved in court.
In the weeks, months and years that followed, the removal of Mr. Boykins unleashed a blizzard of claims, counterclaims and lawsuits, as well as anguish among South Bend’s minority residents over whether an ambitious white mayor had sided with white police officers against a black chief. The day after Mr. Boykins’s dismissal, he was applauded at a gathering of 100 officers, council members and clergy. The events played out against a backdrop of frustration among some African-Americans that they have not benefited equally from an economic resurgence in South Bend, which Mr. Buttigieg extols in his presidential bid.
As Mr. Buttigieg seeks the Democratic nomination in a party whose base is anchored by minority voters, his handling of Mr. Boykins’ dismissal and its messy aftermath raise questions whether the mayor either misunderstood or mishandled sensitivities surrounding race and policing in the place he knew best, a city which is 37 percent black and Latino.
“It felt stomach-churning,” Mr. Buttigieg recalled of the night of the 2012 protest, speaking in an interview. “To know that that same day, we were at what even then I understood was going to be the beginning of an incredibly painful and divisive moment of race relations in my city.”
At that time, Mr. Buttigieg said he removed his police chief because he had lost faith in him after discovering the F.B.I. was investigating him for secretly taping officers’ phone calls. The chief sued the city for racial discrimination over his firing and won $50,000 in 2013. Four white officers sued the city for invasion of privacy and defamation and won a $500,000 payout the same year.
In a political memoir released this year, Mr. Buttigieg wrote that the police tapes case “affected my relationship with the African-American community in particular for years to come.”
Some minority leaders in South Bend say the case is an example of tone deafness on the part of a rising star in the 2020 Democratic field.
Mr. Buttigieg, the first openly gay candidate and the first millennial to seek the presidency, has received a burst of attention and support — measured in $7 million in donations, unexpected strength in polls and mostly positive news coverage.
On Sunday, he kicked off his campaign with a rally in a once-derelict Studebaker auto plant, now sheathed in high-tech glass and home to new businesses. It was evidence of the “turnaround” story of South Bend the mayor tells to rebut skeptics who say America has never elevated a mayor to the White House — much less one who governs fewer citizens than fit in some Big Ten football stadiums.
His accomplishments include the commercial revival of the downtown, a bump-up of 12,000 jobs over his two terms, and the demolition or repair of over 1,000 decrepit houses to attack urban blight.
But there were few people of color at his rally. The former Democratic consultant David Axelrod, a friend of the mayor’s, noted in a Tweet: “Crowd seems very large, very impressive but also very white — an obstacle he will have to overcome.”
Regina Williams-Preston, who represents a majority black district on the South Bend City Council, called Mr. Buttigieg “a smart guy, a nice guy,” but added, “We have to look past the polish and really look at the policy.”
She said minority activists pushed for years for a citizens’ review board that would have a role in police discipline and promotions. At Mr. Buttigieg’s State of the City speech in 2017, she was astonished to hear him cite a longstanding group, the Board of Public Safety, which the mayor appoints, to boast the city now had a citizens’ review board.
“Citizens had asked for a citizens’ review board, and for him to say now we have one, in fact it’s the same thing we’ve always had, that was really disingenuous,” Ms. Williams-Preston said. “Just because you say that doesn’t make it so. To me it was a betrayal.”
At issue in the police taping story are some of the most charged issues in municipal and national politics, including surveillance and personal privacy, government transparency and allegations of racism and unlawful behavior by the police.
Kareemah Fowler, the South Bend city clerk and a political ally of Mr. Buttigieg, said she believed the mayor had worked hard “trying to bridge the gap” between African-Americans and whites in the city.
But Ms. Fowler, whose 2015 campaign backed by Mr. Buttigieg made her the first African-American to hold a full-time executive office in the county, acknowledged that Mr. Buttigieg’s record had not translated into enthusiastic support among black voters for his presidential campaign.
She said the police tapes controversy was a painful episode for the city — and for a young mayor, she said, who had “learned a lot from that experience.”
“Think about his background and where he comes from — Harvard grad, his parents are two professors,” Ms. Fowler said. “He’d probably never been in an environment, prior to that, where he’d had to deal with racial tension.”
Mr. Buttigieg has appointed two white chiefs since ending Mr. Boykins’s tenure. The city has introduced strategies to increase minority trust of officers — implementing body cameras and implicit bias training for officers, and uploading use-of-force incident reports online. But still, minority representation on the department remains low. Only 5 percent of officers were African-American and 5 percent Hispanic in 2018, a slight decline from the previous year.
“Over the years we have had probably 20 minority officers who left their jobs,” said Derek Dieter, a retired South Bend police officer and former City Council president, who is white.
Critics of the mayor say he was too willing to settle multiple lawsuits over the police tapes to make the issue go away, ultimately costing the city close to $2 million. The council itself sued the mayor, trying to get access to the tapes, a case still being litigated, arguing there was no reason for him to withhold them.
Mr. Buttigieg disputes that. Federal and state wiretapping laws, he said, prohibit him from releasing the tapes.
But he also acknowledged that he failed to understand early on the broader racial dimensions of the tapes case, viewing it only “in very legalistic terms.”
“The more that it went on,” he said, “the more protracted and divisive and expensive the issue became, the more clear it was to me there were a lot of other issues at stake that — as not just the policy leader but symbolic leader of the community — I had a lot of responsibility over healing racial divisions, of which this particular incident was just the tip of the iceberg.”
Today none of the four officers heard on the tapes, who held senior roles in the department, still work there. Mr. Buttigieg, who said he has never listened to the tapes because of legal restrictions, doesn’t know if the officers made racist remarks or spoke of illegal activities, as alleged in court filings. The mayor pointed to settlements the city signed with Mr. Boykins and the officers in which all parties acknowledged the absence of evidence of “illegal activity by the plaintiffs” and denied the officers “used any racist word against former Police Chief Darryl Boykins.”
So why did Mr. Buttigieg fire Mr. Boykins in the first place? He maintains he was pressured by federal prosecutors. In “Shortest Way Home,” his memoir published in February, he writes that “a message came through” from prosecutors that he must push out Mr. Boykins or they would file charges against him for violating the Federal Wiretap Act.
Officers in the department had complained to the U.S. Attorney’s Office for Northern Indiana that the chief illegally recorded their phone calls and had threatened to use the tapes against them.
The mayor speculates in his book that prosecutors were trying to duck responsibility for “taking down a beloved African-American police chief” by getting Mr. Buttigieg to fire him instead.
He repeated the explanation this week. “It was made very clear to me by the F.B.I. and the U.S. Attorney that either we would take employment action or there would be indictments,” he said.
Mr. Boykins’s lawyer, Tom Dixon, said that when he first heard this explanation, invoked by Mr. Buttigieg in 2012, a red flag went up. He asked an assistant prosecutor in the U.S. Attorney’s office, a lawyer he knew from church, about the mayor’s assertion.
“He said, ‘Tom, that explanation is so contrary to the protocols of U.S. Attorneys’ offices,”’ Mr. Dixon recalled. “‘We never would condition a determination on prosecuting or not prosecuting based on an employment decision. It would never happen.”
Mr. Boykins has insisted that the recordings were made inadvertently, as part of a longstanding police department practice of taping some phone lines.
The U.S. Attorney informed the city that after a review of the law, no charges would be brought against Mr. Boykins.
After Mr. Buttigieg dismissed Mr. Boykins in March 2012 by asking for his resignation, Mr. Boykins submitted and then rescinded it; Mr. Buttigieg then demoted the chief to the rank of captain. He has since retired. Mr. Boykins did not respond to messages seeking comment.
One person who did hear the tapes was the police communications director, Karen DePaepe. In court filings, she described them as “discriminatory racial comments of high ranking officers” in the department, and said she told Mr. Boykins about them. She also heard “something I believe to be possibly illegal.”
Eleven days after Mr. Boykins’s removal as chief, Ms. DePaepe, who had made eight cassettes of the phone calls and given them to the chief, was fired.
In an interview that night, she told The South Bend Tribune that Mr. Buttigieg’s chief of staff, Mike Schmuhl — who is today his presidential campaign manager — threatened her with arrest if she spoke publicly.
“He said, ‘Now you understand that…you and no one else is allowed to discuss the federal investigation or anything that was recorded,’” Ms. DePaepe said she was told by Mr. Schmuhl, according to the newspaper. “‘And if you or anyone else does, you will be arrested.’”
The city paid Ms. DePaepe $235,000 in 2014 to settle a suit she brought over defamation and other claims. As part of her settlement, she agreed not to discuss what was on the tapes.
A spokesman for the Buttigieg campaign said Mr. Schmuhl recalled his conversation with Ms. DePaepe differently than reported by the newspaper.
Ever since Mr. Buttigieg was first elected in 2011, many in South Bend took for granted that he aspired to higher office, with the support of the local Democratic machine, and was carefully building a record of accomplishments.
One of those goals was bringing businesses and people back downtown. After the city directed tens of millions of dollars to pedestrian-friendly streets and incentives for developers, new hotels, restaurants and apartments sprung up.
Decades of deindustrialization since Studebaker closed its auto plant in the 1960s — and the city lost a quarter of its residents — has been stanched. The population has grown a modest 1 percent, to 102,000, under the mayor.
In his State of the City address last month, Mr. Buttigieg received wave after wave of applause as he ticked off these achievements. “When I go on the road, I talk about our experience as a metaphor for what needs to happen in our country,” he said.
But the benefits have not flowed equally to South Bend’s large minority communities.
Some of the data is dismal. Though the overall poverty rate has fallen since Mr. Buttigieg took office, poverty among African-Americans stubbornly remains almost twice as high as for African-Americans nationwide.
The city has one of the highest eviction rates in the country, which has doubled under the mayor, according to the Eviction Lab at Princeton University.
In households with working adults, 54 percent do not earn enough to meet a “survival budget,” according to the United Way.
The downtown may be a vibrant draw once again for residents, but not everyone can participate.
“You’ve got black people, we’re outside looking in the window at folks enjoying a steak,” said Mario Sims, a pastor and community activist.
Mr. Sims has led protests over the police tapes for years, most recently last summer when a federal appeals court ruled in the case brought by the City Council, known as the Common Council, seeking to make the tapes public.
The case arose when the council subpoenaed Mr. Buttigieg in 2012 to hand over the recordings. The city attorney asked a federal court to rule whether the mayor could comply.
A federal district judge initially decided that some of the recordings could be made public, but an appellate court threw out the case entirely, saying it was not a matter for the federal judiciary. The issue was returned to the state judicial system, in the St. Joseph County courts, where it remains. The city has withdrawn from the fight, leaving it between the council and the police officers, who don’t want the tapes released.
As Mr. Buttigieg campaigns for president well beyond Indiana’s borders, the tapes case and his relations with minorities hang over him. He points out that when he cruised to re-election in 2015, he defeated an African-American primary challenger even in the city’s heavily black Second District.
There are some who say the tapes will never be made public. Others, including Ms. Williams-Preston, the current City Council member from the Second District, expect them to come out and to include material that could inflame racial divisions.
“We have to prepare for that as a community,” she said.
Whenever it happens, she said, Mr. Buttigieg, whose term ends this year, will likely be far away from South Bend. Ms. Williams-Preston, a trainer of special education teachers, is running to take over his job.
“In our culture we want to find a hero,” she said. “But I want people to understand the story of South Bend. Any good story has an imperfect hero, where they struggle with something and they overcome. I’m not sure Pete’s completely overcome. But we’ve given him the opportunity to struggle with some issues.”