Bill Johnson knew, before he reached out to Joseph R. Biden Jr.’s campaign last spring, that things had changed between the former vice president and the nation’s police unions. A once-close alliance had frayed amid clashes over police brutality and racism in the justice system. Still, Mr. Johnson, the executive director of the National Association of Police Organizations, invited Mr. Biden to address the group as it weighed its 2020 endorsement.

For weeks, the campaign was politely noncommittal, Mr. Johnson said. Finally, he recalled, on the day NAPO was deciding its endorsement, he heard from a campaign aide asking if there was still time to send a message. “Not to be a jerk, but we were literally starting the meeting,” Mr. Johnson said. “It’s kind of a little late.”

The police federation, which twice endorsed the Obama-Biden ticket and stayed neutral in 2016, backed President Trump in July. Soon after, its president told the Republican convention that Mr. Biden and Senator Kamala Harris were “the most radical anti-police ticket in history.”

That attack marked a low point in a political relationship that had endured for most of Mr. Biden’s career.

If elected, Mr. Biden would bring to the White House a long career’s worth of relationships with police chiefs, union leaders and policy experts that is unmatched by any other major figure in the Democratic Party, according to more than a dozen current and former law-enforcement officials who have worked with Mr. Biden in various capacities.

During a late-summer speech in Pittsburgh, Mr. Biden pledged to draw both racial-justice activists and police leaders “to the table” to forge durable solutions.

“I have worked with police in this country for many years,” Mr. Biden said. “I know most cops are good, decent people. I know how they risk their lives every time they put that shield on.”

Yet the 2020 election has also underscored the difficulty Mr. Biden may have in achieving that goal. He is presenting himself as both a criminal-justice reformer and a friend to diligent police officers, a critic of racism and rioting alike.

But Mr. Biden has seen his formal support from prominent law-enforcement groups disintegrate as those organizations closed ranks against reform legislation. They have objected to Mr. Biden’s rhetoric about “systemic racism” in policing and to his vows to regulate police agencies with federal power, even as reformers on the left press Mr. Biden to take up far bolder changes.

Some of Mr. Biden’s colleagues from the Obama administration, including Eric H. Holder Jr., the former attorney general, have worked to organize law-enforcement backing for Mr. Biden outside traditional police groups, and in September the campaign released a long list of endorsements stocked heavily with former sheriffs and prosecutors. Yet Mr. Trump has relentlessly exploited gaps between Mr. Biden and police leaders, running television ads accusing Mr. Biden of siding against the police in a time of unrest and berating him at the first presidential debate about his lack of police endorsements.

Mr. Biden’s response in that debate captured the risky political assumption of his candidacy, and a potential Biden presidency: that through a combination of good faith and long relationships, he might bring about peace between warring factions.

“What I’m going to do as president of the United States is call together an entire group of people at the White House,” Mr. Biden promised. “Well, everything from the civil rights groups, to the police officers, to the police chiefs, and we’re going to work this out.”

ImageJoe Biden Had Close Ties With Police Leaders. Will They Help Him Now?
Credit…Stephen Crowley/The New York Times

Daryl F. Gates was already notorious when he visited Capitol Hill in the fall of 1990. In his 12 years leading the Los Angeles Police Department, he had become one of the country’s most polarizing supercops: a high-profile field marshal in the war on drugs who dismissed concerns about racism and police brutality. Addressing the Senate Judiciary Committee on drug control that September, Mr. Gates told lawmakers that casual drug users “ought to be taken out and shot.”

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If the draconian phrasing startled the committee’s chairman, the 47-year-old Senator Biden of Delaware, he did not say so. Concluding the hearing, Mr. Biden lauded Gates and another chief testifying with him, Lee P. Brown of New York City, the country’s most prominent Black policeman.

“Thank God,” Mr. Biden said, “you are both so darn competent.”

Within six months, the tone of admiration between Mr. Gates and Mr. Biden was gone. When several white police officers in Los Angeles brutally beat Rodney G. King, a Black man, Mr. Biden called on Mr. Gates to resign. The chief responded with mockery, invoking the plagiarism scandal that scuttled Mr. Biden’s first presidential campaign.

Of the demand that he quit, Mr. Gates said, Mr. Biden “probably heard it said somewhere else and is repeating it.”

It was a preview for Mr. Biden of how quickly a relationship forged over battling crime could unravel in a clash over racism in policing.

For years, Mr. Biden stood out in the Senate as a fierce defender of the police. He has alluded, during the current campaign, to an affinity for law enforcement dating to his Irish Catholic upbringing in Pennsylvania and Delaware. (“There were three things all my friends became,” he said in a September town hall, “a cop, a firefighter and a priest.”)

And he has spoken over the years about being drawn to issues of racial justice and public order after witnessing, in his youth, both the breakthroughs of the Civil Rights Movement and the tragedy of rioting in Wilmington, Del., after the assassination of the Rev. Dr. Martin Luther King Jr. — events that may have underscored, in a young politician’s mind, the fragility of political support for large-scale social change.

As a young senator, Mr. Biden sought a spot on the Judiciary Committee. Determined not to let Republicans outflank his party in confronting a national crime wave, Mr. Biden spent the 1980s advancing law-and-order policies like the creation of a federal anti-narcotics office led by a “drug czar,” a title he is often credited with coining.

By 1994, Mr. Biden had partnered with police groups to devise the Violent Crime Control and Law Enforcement Act, a sprawling law that poured money into enforcement, banned assault-style weapons, toughened sentences for drug- and gang-related offenses and expanded the federal death penalty, among other measures.

The bill was so sweeping in its scope and so stern in its penalties that it came to be a political liability for Mr. Biden in this year’s Democratic primaries. At the time, it was a popular achievement that thrilled police groups.

“This translated into a tremendous amount of good will for Biden, both nationally and in his home state,” said James Pasco, the executive director of the Fraternal Order of Police, a group currently supporting Mr. Trump.

Mr. Brown, who went on to serve as the drug czar in the Clinton administration and later became the mayor of Houston, said Mr. Biden had always been inquisitive about what the police needed in order “to be more effective in carrying out our responsibilities.”

“He was just upfront in his support of law enforcement,” said Mr. Brown, recalling that Mr. Biden would ask: “What could the Congress do to be more helpful?”

But often left out of those conversations, Biden allies acknowledged, were issues of racial bias and police misconduct. And if Mr. Biden formed deep relationships with police leaders over fighting crime, those bonds have deteriorated during the extended reckoning over racism that has stretched from the Ferguson, Mo., protests of 2014 into the present day.

William J. Bratton, who served twice as New York Police Department commissioner, said Mr. Biden had long enjoyed “very strong support among the police,” spanning internal divisions in the law-enforcement community.

But Mr. Bratton also acknowledged that issues of police racism had not factored prominently into their collaboration. “We did not have those discussions,” he said.

Credit…Stephen Crowley/The New York Times

It was during the 2008 presidential transition, as autumn turned to winter after the election, that Mr. Biden, as vice president-elect, told a few police officials that he planned to be their point of contact in the new administration.

“He said that he told the president: I want to keep law-enforcement in my portfolio,” recalled J. Thomas Manger, then the police chief in Montgomery County, Md., a suburb of Washington, D.C. “At one of our first meetings, he said to me, ‘I’ve always been with the cops. You’ve always been my guys.’”

Mr. Obama and Mr. Biden entered office confronting multiple urgent crises, with a mandate to rescue the economy and resolve failing wars in Iraq and Afghanistan. Violent crime was receding as a political issue and the law-and-order ethos of the 1990s was drawing new skepticism, particularly on the left. Special envoy to the cops was not a particularly coveted assignment.

Mr. Biden embraced it with vigor. During meetings at the Executive Office Building and breakfasts at the Naval Observatory, Mr. Biden functioned dually as peacemaker and political whip. Early on, he helped rouse support from police groups for the Recovery Act and the president’s first Supreme Court appointee, Justice Sonia Sotomayor, helping the administration sell her nomination to the political middle.

“He was a terrific ambassador for the Obama presidency, for law enforcement,” said Laurie Robinson, a former assistant attorney general whose office distributed grants to police agencies. “That made a tremendous difference in the ability to work not just with the leadership organizations, but with the unions.”

On sensitive subjects like immigration and gun control, Mr. Biden sought advice from his longtime allies in the law-enforcement world, asking for guidance on how best to attract police support for Mr. Obama’s agenda amid signs that the law-enforcement community was shifting rightward. One ally was Chuck Wexler, the head of the Police Executive Research Forum, a law-enforcement think tank.

Mr. Wexler recalled a meeting about immigration in Mr. Biden’s suite at the Executive Office Building: In the moments before it began, Mr. Wexler said, a vice-presidential aide pulled him aside and ushered him into a tiny room where Mr. Biden was waiting. “Listen, you and I, we’ve got history,” Mr. Biden said, according to Mr. Wexler. “Tell me: How do these folks feel about immigration? What do I need to know?”

Gil Kerlikowske, a former Seattle police chief who worked closely with Mr. Biden as the top federal drug-control official, said Mr. Biden has spoken frankly about the value of enlisting law-enforcement leaders in the pursuit of progressive goals. The former vice president, he said, saw public safety as a foundational issue for most voters — one on which they would not excuse failure.

“The safety and security issue, to the public, is an important one,” said Mr. Kerlikowske, who described Mr. Biden as walking a “very fine line” in the current campaign.

In their work together, Mr. Kerlikowske said he had not previously heard Mr. Biden use language like “systemic racism,” though he said the former vice president was sensitive to the issue of bias.

Mr. Biden performed important ceremonial functions, too: He handed out the Medal of Valor, an award for police heroism, and hosted events at his residence for National Police Week. In 2014, when a gunman targeted and killed two New York Police Department officers, Mr. Biden addressed the funeral of one, Rafael Ramos, and visited the family of the other, Wenjian Liu, at their Brooklyn home.

Mr. Bratton, who also spoke at Ramos’s funeral, said Mr. Biden approached him there to compliment a turn of phrase in his eulogy: “We don’t see each other: the police, the people who are angry at the police,” the commissioner had said, promising, “When we see each other, we’ll heal.”

“He was very taken with that expression,” Mr. Bratton said with evident pride. “He uses it to this day.”

Mr. Biden echoed the sentiment in a different context not long ago, after the killing in May of George Floyd, a Black man, by Minneapolis police.

“To everyone speaking out and peacefully demanding justice across the nation,” he tweeted in June, “I see you, I hear you and I stand with you.”

Credit…Andrew Renneisen for The New York Times

In the summer of 2016, Mr. Biden sat with Mr. Obama in the Roosevelt Room at the White House, an array of police leaders before them. Five police officers had been gunned down in Dallas by a man driven by animus against law enforcement. The president and vice president both pleaded with union leaders to temper their rhetoric about a nationwide “war on cops.”

The vice president, Mr. Johnson recalled, made a personal appeal to the police groups, to the effect of: “You know me, you can trust me, I’ve always been there for you.”

“I think it fell flat,” Mr. Johnson said. “For the representatives around the table of various law-enforcement groups, our perception was, things were very bad out there.”

As early as 2009, there had been at least faint signs of tension. One was the uncomfortable episode that summer when Mr. Biden helped chaperone a so-called beer summit between Mr. Obama, Henry Louis Gates Jr., a professor at Harvard University who was arrested at his own home after a passer-by reported a suspected robbery, and Sgt. James Crowley of the Cambridge, Mass., police, who had arrested Mr. Gates. Mr. Obama said the Cambridge police had “acted stupidly,” enraging police groups.

The challenges to come would dwarf that episode by orders of magnitude.

The lethal shooting of Michael Brown, a Black teenager in Ferguson, Mo., by a white officer in 2014 opened a new period of tumult in law enforcement and race relations. By the summer of 2016, a mood of crisis had taken hold, as the country confronted the successive killings of two Black men, Alton Sterling and Philando Castile, in Louisiana and Minnesota, and of the officers in Dallas.

For Mr. Biden, it was no longer an option to focus on the mechanics of crime-fighting over matters of race.

Mr. Biden repeatedly summoned chiefs and union leaders to his residence and his office, and backed an administration task force charged with drafting a reform agenda. Ms. Robinson, who co-chaired the panel, said Mr. Biden’s involvement helped secure cooperation from wary police groups, calling it “a reflection of his real sensibility about tone, and how things are being received, and the role that he can play in those situations.”

Ronald L. Davis, a member of the task force who previously headed the federal Community Oriented Policing Services program, which gives funding to police departments, said Mr. Biden had been emphatic that the panel had to “come up with real solutions,” not just generate a report. (The group’s work was largely dismantled by the Trump administration.)

Without Mr. Biden’s involvement, it is possible that an insuperable rift would have opened between the administration and crucial law-enforcement groups. Mr. Wexler described a session at the Naval Observatory in the aftermath of Ferguson, when police chiefs and union leaders were at loggerheads.

“The police chiefs were pushing for reform, the unions were digging in and Biden had all of us to his residence,” Mr. Wexler said. “He mediated, in the sense that he let people talk, and if nothing else he was the convener, because everybody knew him.”

But if Mr. Biden’s easy manner and concern for cops helped bring police groups to the table, some law-enforcement leaders felt a mounting sense of grievance as they saw the administration take up a reform agenda. Mr. Pasco, of the Fraternal Order of Police, said that for all Mr. Biden’s heartfelt outreach, he was still “on the anti-police side of these issues.”

Credit…Erin Schaff/The New York Times

At the same time, Mr. Trump was mounting his first campaign for the presidency on a simpler message: one of unyielding support for law enforcement and near-total indifference to police brutality. Accepting his party’s nomination in 2016, shortly after the Dallas shooting, Mr. Trump said such attacks “threaten our very way of life.”

In the intervening years, Mr. Trump’s message has scarcely changed, while Mr. Biden’s task has grown more complicated. The racial-justice movement challenging traditional policing has only gathered strength, while police groups have embraced increasingly strident and alarmist rhetoric about rioting and violent crime. And Mr. Biden’s determination to bridge those divides has persisted.

Rich Stanek, a former Republican sheriff in Hennepin County, Minn., who worked with Mr. Biden on gun control during his vice presidency, questioned how much good will Mr. Biden would have to draw on with police groups as president. Yet he and other police leaders did not discount the possibility of a shift if Mr. Biden wins the election.

“It’s the president,” Mr. Stanek said. “If he calls and invites law enforcement to his office to talk about an issue, they’re going to come.”

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