Where were you when you first heard about the Snowden leak?

The huge breach of the National Security Agency’s domestic surveillance program in June 2013 was one of the proudest moments in modern journalism, and one of the purest: A brave and disgusted whistle-blower, Edward Snowden, revealed the government’s extensive surveillance of American and foreign citizens. Two journalists protected their source, revealed his secrets and won the blessings of the Establishment — a Pulitzer Prize and an Oscar for it.

One of the people who fell in love with that story was Pierre Omidyar, the earnest if remote billionaire founder of eBay. That October, he pledged $250 million for a new institution led by those two journalists, Glenn Greenwald and Laura Poitras. Mr. Omidyar was the benefactor of journalists’ dreams. He promised total independence for a new nonprofit news site, The Intercept, under the umbrella of his First Look Media. The Intercept was founded in the belief that “the prime value of journalism is that it imposes transparency, and thus accountability, on those who wield the greatest governmental and corporate power.” The outlet’s first mission was to set up a secure archive of Mr. Snowden’s documents, and to keep mining them for stories.

The recent history of the news business has been about what happens when your traditional business is disrupted by the internet and your revenues dry up. But at The Intercept and First Look, the story is of a different destabilizing force: gushers of money.

In 2017, the for-profit arm of the company had budgeted $40 million for a growing staff and bets on movies and television shows, a former executive said, while the nonprofit arm spent about $26 million in 2017 and again in 2018 according to its public filings, most of it on The Intercept.

High-profile stars collected big salaries — Mr. Greenwald brought in more than $500,000 in 2015 —  and they sometimes clashed in public with their titular bosses over the rocky efforts to build an organization. Writers warred on Twitter and in Slack messages over Donald Trump, race and the politics of the left. Mr. Greenwald continues to infuriate younger colleagues with tweets like one denouncing “woke ideologues.”

Not long after Mr. Omidyar wired his first dollar, he found himself presiding over chaos so public that Vanity Fair asked in 2015 “whether First Look Media can make headlines that aren’t about itself?”

All the drama would make this another colorful story about extreme newsroom dysfunction had The Intercept not caught the attention of a naïve National Security Agency linguist with the improbable name of Reality Winner in 2017. Ms. Winner, then 25, had been listening to the site’s podcast. She printed out a secret report on Russian cyberattacks on American voting software that seemed to address some of Mr. Greenwald’s doubts about Russian interference in the 2016 campaign and mailed it to The Intercept’s Washington, D.C., post office box in early May.

The Intercept scrambled to publish a story on the report, ignoring the most basic security precautions. The lead reporter on the story sent a copy of the document, which contained markings that showed exactly where and when it had been printed, to the N.S.A. media affairs office, all but identifying Ms. Winner as the leaker.

On June 3, about three weeks after Ms. Winner sent her letter, two F.B.I. agents showed up at her home in Georgia to arrest her. They announced the arrest soon after The Intercept’s article was published on June 5.

“They sold her out, and they messed it up so that she would get caught, and they didn’t protect their source,” her mother, Billie Winner-Davis, said in a telephone interview last week. “The best years of her life are being spent in a system where she doesn’t belong.”

Failing to protect an anonymous leaker is a cardinal sin in journalism, though the remarkable thing in this instance is that The Intercept didn’t seem to try to protect its source. The outlet immediately opened an investigation into its blunder, which confirmed the details that the Justice Department had gleefully announced after it arrested Ms. Winner. They included the fact that The Intercept led the authorities to Ms. Winner when it circulated the document in an effort to verify it, and then published the document, complete with the identifying markings, on the internet.

Internal emails and records I obtained reveal the tumult that led to one of the highest-profile journalistic disasters in recent memory and provide broader insights into the limits of a news organization dependent on an inattentive billionaire’s noblesse oblige. A spokeswoman for Mr. Omidyar declined to make him available for an interview. The New York Times is not publishing the documents, which run to more than 100 pages, because they include discussions of sourcing and security measures.

The documents, among them two internal reports on the Reality Winner incident that have not been made public, were given to me by people who were senior employees in 2017 and contend that the organization failed to hold itself accountable for its mistakes and for what happened to Ms. Winner as a result.

Some current and former staff members I interviewed expressed fundamental questions about the internal investigation into the debacle, including why The Intercept hadn’t brought in an outside law firm or other independent entity to conduct the inquiry, and they also asked why Betsy Reed, the editor in chief, had assigned the investigation to Lynn Dombek, then The Intercept’s head of research, who reported directly to her.

Ms. Reed, who had been brought in to stabilize The Intercept and rein in its big personalities in 2015, told me she faced “a treacherous situation” after the article was published. She needed to balance a “legitimate demand for transparency” that aligned with The Intercept’s founding values with lawyers’ strong advice to stay silent to protect her reporters and their sources.

Ms. Poitras said The Intercept should have held itself to a higher standard.

“We founded this organization on the principle of holding the powerful accountable and protecting whistle-blowers,” Ms. Poitras said in an interview. “Not only was this a cover-up and betrayal of core values, but the lack of any meaningful accountability promoted a culture of impunity and puts future sources at risk.”

The internal tensions were boiling over one night, just before Thanksgiving 2017, when the two American journalists who helped bring Mr. Snowden’s revelations public were exchanging late-night emails, which I obtained. They were writing not about government misconduct, but their own newsroom’s.

Ms. Reed’s oversight of the investigation, Ms. Poitras wrote, was an attempt “to cover up what happened for self-protective reasons.”

It was, Mr. Greenwald agreed in response, a “whitewash.”

The documents fall short of revealing a conspiratorial cover-up. Instead they show an extreme version of the human errors, hubris and mismanagement familiar to anyone who has worked in a newsroom — and the struggle of The Intercept to live up to its lofty founding ideals in dealing with its own errors.

Ms. Winner may have thought she was mailing the documents to Mr. Greenwald and Ms. Poitras, who went to great lengths to protect Mr. Snowden. But Mr. Greenwald was in Brazil and when he heard about the document, he was not interested. He told me that he considered its claims about Russian hacking during the 2016 race “wildly overblown” and that it didn’t include direct evidence to persuade him otherwise.

Ms. Poitras, meanwhile, had at that point left The Intercept, and gone on to establish a nonprofit production firm, Field of Vision, a part of First Look Media, which also includes The Intercept and Mr. Omidyar’s other ventures.

Ms. Reed and her deputy, Roger Hodge, gave the story to a pair of established television journalists: Matthew Cole and Richard Esposito. Mr. Cole, formerly of NBC, had collaborated with Mr. Greenwald on the Snowden stories and was on staff. Mr. Esposito, also a veteran of broadcast news at NBC News and ABC News, was brought in from outside and is now the top spokesman for the New York Police Department.

Ms. Reed told me she’d brought them in partly because The Intercept’s outsider posture had left it without the inside sources who could verify documents like Ms. Winner’s. But their reflex to reach out to national security officials carried its own risk.

“If you get a document that purports to be from the N.S.A., it should be a five-alarm fire,” a member of The Intercept’s high-powered security team, Erinn Clark, said in her interview for the internal inquiry. “Go to a secure room, with an editor, freeze where you are. You are not aware who you are exposing or putting at risk.”

Instead, Mr. Cole put the document in his bag and got on a train to New York.

One concern did cross his mind.

“I thought at the time there would be an audit if they printed on a government printer,” he said, according to the internal review notes. “I forgot about that thought.”

Later, he called a source in the intelligence community in an attempt to verify the document, and casually revealed its postmark.

”My source said something about, ‘How did it come to us?’ I said in the mail, from Georgia, and my source laughed about that,” he recalled during the internal investigation. Then, Mr. Cole mentioned that the postmark was Fort Gordon, Ga., which is home to the N.S.A.’s Cryptologic Center. “‘There’s a logic to that,’ the source said.”

The startling carelessness about protecting Ms. Winner was particularly mystifying at an organization that had been founded on security. The Intercept had hired leaders in digital security, Ms. Clark and Micah Lee, for just such situations. Mr. Cole did not involve them at all.

Mr. Cole and Mr. Esposito said they’d been pushed to rush the story to publication, but Mr. Cole also acknowledged that failing to consult with the security team was a “face plant.”

The Intercept’s leaders argued in 2017, and still contend, that the narrative laid out by the Justice Department in its prosecution of Ms. Winner was shaped to make The Intercept — a thorn in the government’s side — look bad. And Ms. Winner’s own carelessness — she printed the document at work — could easily have gotten her caught even if The Intercept had been more cautious. But they also knew they had made real journalistic errors.

And so a key question was who to blame for this catastrophe and what consequences they should suffer. Ms. Dombek, who undertook the internal investigation, concluded that the editors — Ms. Reed and Mr. Hodge — needed to take responsibility. Others, including Mr. Greenwald, were demanding that Mr. Cole and Ms. Reed be fired, and The Intercept provide a public reckoning. (Mr. Greenwald later relented, and said he understood the desire not to “scapegoat” for an institutional failure.)

On July 11, 2017, Ms. Reed published a post on The Intercept announcing that First Look would pay for Ms. Winner’s legal defense. Ms. Reed also announced that an “internal review of the reporting of this story has now been completed.”

“We should have taken greater precautions to protect the identity of a source who was anonymous even to us,” she wrote. “As the editor in chief, I take responsibility for this failure, and for making sure that the internal newsroom issues that contributed to it are resolved.”

But the drama didn’t end there.

Mr. Greenwald and Jeremy Scahill, an investigative reporter who is the third founder of The Intercept, publicly demanded a more thorough investigation, and in response to their pressure, the company commissioned a second internal report, by a First Look lawyer, David Bralow. Mr. Bralow’s report, issued four months later, cited as central issues the decision to share the document with the N.S.A., Mr. Cole’s discussion of the postmark and the publication of the identifying markings.

“While each of these actions may or may not amount to an error in all cases, in this instance, these actions fell below The Intercept’s goals of protecting sources who seek to share information of significant public importance,” he wrote. “The procedures for authenticating leaked, classified documents reveal institutional weaknesses.”

Ms. Winner was sentenced to five years and three months in federal prison in 2018, and The Intercept has covered her case regularly, always noting its own role — “an important part of accountability,” Ms. Reed said.

But there hasn’t been any further accounting. Neither internal report was shared with the public. Nobody at The Intercept was fired, demoted or even reassigned.

Ms. Reed and Mr. Bralow argued that any public reckoning could still expose other sources they spoke to about the document.

The story has clearly been a psychic blow to the idealism that marked the founding of The Intercept. The outlet has stepped back from its early ambitions. The archive of Snowden documents, which it received from Mr. Greenwald and Ms. Poitras on the condition that the company maintain a specific, complex security protocol and a staff to support it, was closed after Ms. Reed reduced its staff, citing budget cuts. Ms. Poitras, who furiously objected to the cuts at the time, called the move “staggering.”

The repository had been “the most significant historical archive documenting the rise of the surveillance state in the twenty first century,” Ms. Poitras wrote in a memo to The Intercept’s parent company. Closing it did a disservice to “the public for whom Edward Snowden blew the whistle.”

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The Intercept never fully regained its swagger after the Reality Winner case, though it has continued to produce notable stories. It has broadened its original mandate to reporting on “civil liberties, social justice, the fight against corruption,” Ms. Reed said, and broken stories including revelations from the Snowden files of AT&T’s role in N.S.A. surveillance and an investigative profile by Mr. Cole of Erik Prince, the founder of the private security contractor Blackwater.

Nowadays, it seems more taken by politics, both in Brazil, where Mr. Greenwald lives, and in the United States, where it has become a hub for the fiery ideological battles playing out among the American left.

A leak to Mr. Greenwald last year showed how corruption investigations had been politicized in Brazil; the reporting reshaped the country’s politics. In the United States, Mr. Greenwald has been increasingly engaged in the bitter feuds with others on the left, charging that liberals — including some of his Intercept colleagues — have become fixated on identity politics and Russia, and ignored the more insidious workings of corporate power. His most memorable television appearances these days seem to be on Fox’s Tucker Carlson show, during which the two men denounce the so-called “deep state.”

Meanwhile, his colleagues have refashioned the site to champion insurgents and critics of the Democratic mainstream, including a woman who accused Joe Biden of sexual assault, Tara Reade, as mainstream outlets raised doubts about her story.

The business conceived to underwrite the journalism at The Intercept — the for-profit moviemaking arm — has sputtered, too, failing to produce another hit since “Spotlight” in 2015. The documents I obtained show a bitter internal fight over leaders’ refusal to give a top female executive a producer credit. Another of its highest-profile hires, the former Topic.com editor Anna Holmes, who left in 2019, told me: “I’ve always admired First Look Media’s stated commitment to free speech, transparency and speaking truth to power. So in that spirit I’ll say this: My tenure there was creatively rewarding — it was also personally and professionally demoralizing.”

Reality Winner, meanwhile, is recovering from the coronavirus in federal prison in Texas. She’s still short of breath sometimes, said her mother, who still blames The Intercept for the disastrous consequences of her daughter’s incautious effort to blow the whistle, though First Look is also paying the legal bills.

Ms. Winner-Davis recently abandoned her retirement to take a job as a corrections officer at a local jail so she could feel closer to her daughter, and understand her experience behind bars.

“It tears me apart every day going into that setting and knowing this is what my daughter is going through,” she said.

New York City’s largest police union had not endorsed a candidate for president in decades when its leader, Patrick J. Lynch, stepped to the lectern last month at President Trump’s golf club in New Jersey.

“Mr. President, we are fighting for our lives out there,” Mr. Lynch said, in the all-caps cadence familiar to any casual viewer of the New York nightly news. “We don’t want this to spread to the rest of the country. We need your strong voice across the country.”

Mr. Lynch said his union, the Police Benevolent Association, was endorsing Mr. Trump because city and state leaders had been relentlessly scapegoating hard-working police officers and allowing chaos to reign on the streets.

But another factor that may have played into the P.B.A.’s endorsement could be seen in the imagery surrounding him: Joining Mr. Lynch before a sea of mostly white union members were three of his top colleagues, each of them a white Republican from conservative strongholds in Staten Island or Long Island.

The tableau of the four union leaders standing together with Mr. Trump reflected a larger truth about the upper ranks of the city’s police unions: Even as the Police Department has become more diverse and is now less than half white, the unions continue to be run mostly by white conservatives who live in the suburbs and increasingly echo the president’s views.

Nearly 90 percent of the police unions’ leaders — officers, trustees, financial secretaries — are white and even more are men, according to an analysis of public records by The New York Times. Close to 70 percent are registered Republicans and more than 60 percent live on Long Island or in counties north of New York City, the analysis found.

The demographic gap helps explain the political spectacle and cultural gulf on display in recent weeks as New York City police union leaders have stridently repeated the president’s mayhem messaging and attacked Black Lives Matter protests in scathing terms.

This is occurring in a city where Mr. Trump is deeply unpopular, only a third of residents are white and the Democratic establishment has embraced the nationwide campaign against police brutality and racial bias.

While some Black and Hispanic police fraternal groups objected to Mr. Lynch’s endorsement of the president, there is no evidence of a broader backlash among rank-and-file members to the announcement of support, nor to Mr. Lynch’s speech last month praising the president at the Republican National Convention.

Still, the demographics of the police unions’ leadership set it starkly apart from a majority of the department’s 36,000 uniformed officers and from the wider population of New York.

Like President Trump, Mr. Lynch and his colleagues have chosen to characterize the current round of protests not as a moment of historical reckoning over systemic racism, but instead as one of chaos sowed by the “radical left.”

Mr. Trump has in turn amplified those views. On Sunday, he responded to a tweet from Mayor Bill de Blasio encouraging New Yorkers to enjoy the nice weather by saying, “People don’t want to get mugged, beaten up, or killed. Let New York’s Finest (who proudly endorsed me!) do their job.”

As they have done for years, the union leaders have set themselves against the momentum for change. They have fought a city law that made it a misdemeanor for police officers to use chokeholds during arrests, and tried to stop a state law that makes officers’ disciplinary records public. And they have fiercely opposed a state law ending the use of cash bail for most nonviolent offenders in New York.

City and state officials said the police unions have largely given up on traditional lobbying and back-room negotiations since their main political allies, Republican lawmakers who controlled the State Senate, lost power two years ago. The police union leaders have instead leaned more heavily than ever on incendiary public attacks on liberal politicians and their allies.

In June, for instance, when the unions faced certain defeat in a long battle to keep their members’ disciplinary records secret, they conceded as much to several state lawmakers and asked for only small concessions, according to two lawmakers approached by the unions.

Mr. Lynch has not met with Mayor de Blasio in more than three years, city officials said. Nor, the officials added, did the P.B.A. or other police unions make any attempt to lobby the City Council before it took up a package of police oversight bills this spring or moved weeks later to shift nearly $1 billion from the Police Department’s budget.

Instead, the officials pointed out, Mr. Lynch held a news conference near City Hall with his fellow union leaders, lashing out at local politicians. “For our legislators to demonize police officers, as if we’re the problem, as if we broke the windows, as if we caused the violence, that is absolutely outrageous,” Mr. Lynch said.

Asked about the police unions’ approach, Bill Neidhardt, a spokesman for Mr. de Blasio, said, “They have shifted out of policy and representation and into politics. And not just any politics but the politics of the far right. It’s a step to the extreme.”

The P.B.A. declined requests to interview Mr. Lynch and the other three union leaders at the Trump endorsement. Mr. Lynch also would not respond to questions about his relationship with Mr. Trump or with the city’s communities of color.

In a statement, Mr. Lynch played down the disparity between the police union leadership and the rank and file, saying the P.B.A. was unified under his watch.

“The secret of our solidarity isn’t complicated,” he said. “No matter where we live or what we look like, police officers’ concerns are the same.”

But his endorsement of Mr. Trump, coming after years of opposition to police reform, has disturbed some city officials, and deepened their disillusionment with what they have described as a reactionary stance by the police unions.

“When people in my community hear Pat Lynch speak, what they hear is hatred being spewed,” said Donovan Richards Jr., a Black Democrat from Queens who chairs the public safety committee of the City Council.

Many Black and Hispanic officers said they did not feel represented by their unions, a sense of disconnection that was heightened by the P.B.A.’s endorsement.

“Who are the unions’ shot callers?” asked Detective Felicia Richards, who leads the Guardians Association, a fraternal organization for Black officers. “It’s pretty much still a good old boys’ club.”

Last month, the Guardians Association condemned the endorsement of Mr. Trump and said that while Mr. Lynch had served his members well in some ways, he reached the decision to endorse without even conferring with his union.

Charles Billups, chair of the Grand Council of Guardians, a statewide organization for Black police officers, said Mr. Lynch’s support of Mr. Trump put many active Black officers in the awkward position of opposing people who — at least in theory — were meant to represent them in contract negotiations, disciplinary proceedings and other aspects of their jobs.

“Do we speak out against it and end up being blackballed or ostracized by people we work with every day?” Mr. Billups asked. “Or do we just go along to get along?”

The police union’s embrace of Mr. Trump has been gathering steam all year, but it came to a head last month when Mr. Lynch, a registered Democrat with conservative views, spoke at the Republican convention.

During his address, Mr. Lynch offered New York as a case study backing one of Mr. Trump’s central campaign arguments: that the nation’s cities were under siege by anarchists and criminals.

“Why is this happening?” he asked. “The answer is simple: The Democrats have walked away from us.”

The speech and the endorsement were the culmination of a decades-old campaign to pressure politicians on law and order issues, at times using fear-mongering tactics or language with a clear racist subtext.

Most notoriously, the P.B.A. held a rally in 1992 against the city’s first and only Black mayor, David N. Dinkins. Hundred of union members carried signs with sayings like “Dear Mayor, have you hugged a drug dealer today” and “Dinkins, We Know Your True Color — Yellow Bellied.” Some officers were also reported to have used racial slurs.

Two weeks ago on Twitter, the P.B.A.’s sister union, the Sergeants Benevolent Association, referred to Councilman Ritchie Torres, who is Afro-Latino and gay, as a “first-class whore.” Mr. Torres, the Democratic candidate for a Congressional seat in the Bronx, had called for an investigation into a possible police slowdown during a spike in gun violence.

So far, Mr. Lynch has been the only police union leader in New York to endorse Mr. Trump, but Edward D. Mullins, who runs the sergeants’ union, and Paul DiGiacomo, the head of the Detectives’ Endowment Association, have both come close.

Echoing the president, the three men and their aides have gone on television and social media to blame the rise of shootings in New York on what they have described as failed liberal policies. Some have called on Mr. Trump to send federal officers to the city. Others have launched Trump-like cultural attacks comparing protests around the country to Nazi rallies.

Union leaders have also complained about a “progressive violence plague” in New York and praised Mr. Trump as the only politician with the strength and courage to stand up for the police.

Mr. Mullins has even appeared on Fox News with a mug in view emblazoned with a logo for QAnon, a conspiracy theory that holds that a cabal of satanic pedophiles is intent on defeating Mr. Trump.

As early as February, Mr. Mullins visited the White House to talk about the “plight of police officers in NYC,” as he wrote on Twitter:

“@realDonaldTrump has our backs!” he said.

In the months that followed, Mr. Mullins went to war with Mr. de Blasio, blaming him for a litany of local crimes and launching personal attacks that culminated one day late last month when he demanded the mayor resign by “sundown.”

Employing similar themes, Mr. DiGiacomo gave a recent interview on YouTube in which he displayed framed photos of himself with Mr. Trump and of his father, a onetime city transit officer.

Mr. DiGiacomo said he had never seen New York at such a low point and blamed the city’s problems on police reform laws, feckless district attorneys and Democrats like Mr. de Blasio and Gov. Andrew M. Cuomo who, he said, had given up on supporting New York officers.

While he acknowledged he was not yet formally backing Mr. Trump, Mr. DiGiacomo added: “The way we see it right now, there’s only one person out there standing up for the police.”

Not quite half — or 47 percent — of the city’s uniformed officers are white, police officials say. Twenty-nine percent are Hispanic and 15 percent are Black. Asian officers make up 9 percent of the force.

The union leadership, however, is 88 percent white, according to listings posted on their websites and in tax reports. Hispanic officials account for 7 percent of the upper ranks. Black officials make up only 5 percent.

There is a similar divide in where officers and union leaders live. In 2016, the last year that detailed data was available, 58 percent of all New York officers lived in one of the city’s five boroughs. Long Island was home to 26 percent and about 13 percent lived in one of four northern counties.

But according to public records, only 36 percent of union leaders live within the city. Most — 44 percent — live on Long Island. Another 19 percent make their homes in the nearby northern suburbs. Twenty percent live on Staten Island or in largely white neighborhoods in Queens.

As for politics, voting records indicate that a majority of union leaders — 68 percent — are registered Republicans. Twenty-six percent identify as Democrats, the records show, and 5 percent have no party or another affiliation.

Asked if union leaders reflect their members, Mr. Lynch noted in his statement that his administration, which has been in power for more than 20 years, had appointed both the first Black and first Hispanic officials to the union’s top three slots.

He also pointed out that he had been elected to a fifth term in 2015 with 70 percent of the vote and a sixth term last year after running unopposed.

In an interview, Mr. Mullins said his own membership was well served by its leaders “regardless of their color or ethnic background.” If they were not, he added, “I would expect them to say something about it.”

The son of an Irish longshoreman and a Latina homemaker, Mr. Mullins said that officers of color had not yet had a chance to rise through the union’s ranks.

“People have to go through the process of getting elected and putting in time to get to the top,” said Mr. Mullins, who has run the union since 2002. “The mechanism is there. We just have to allow time to take its course.”

Some former high-ranking officers, however, said the union leadership was less diverse than the department because an old guard of leaders has had a lock on power.

“It’s a network,” said Robert Gonzalez, a former president of the Latino Officers Association who is now a professor of criminal justice at St. John’s University. “They mentor each other. They steer people to vote a certain way. They navigate them and endorse certain people. And it just so happens that those people are white men.”