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The 96-year-old magazine, known for its revered writers and sophisticated audience, is being consumed by a labor dispute.

Writers for The New Yorker have been known to refer to the editor, David Remnick, as “Dad,” so there was something a little illicit about their decision to gather without him back in 2018 at a Windsor Terrace apartment.

Some 20 of the writers, many of them marquee names, were getting together to decide how to react to the surprise announcement that their less heralded colleagues — fact checkers, copy editors, web producers, social media editors — were forming a union and demanding raises.

The writers discussed whether they should follow their junior colleagues into the NewsGuild, and whether the magazine treated writers fairly.

George Packer broke with the magazine’s tight-lipped traditions by sharing details of his own deal with Condé Nast. He told his colleagues that after years of reporting from Iraq, he had requested and received health insurance before the birth of his first child. Other writers were shocked, according to several people who were there. Under The New Yorker’s structure, even some of the best-known writers are considered “contractors,” and their bosses had given them the impression that health insurance was not a possibility.

An organizer for the NewsGuild who was present, Nastaran Mohit, told the writers she had avoided involving them in the original organizing drive because she knew how close many of them were to management, and she was worried they’d snitch.

But she also said the NewsGuild believed the writers were misclassified as contractors, when they were really akin to full-time employees, and she laid out a path for them to join the union. She told them, two people in the room said, that the guild could protect them from being fired and could even defend them against misguided editorial choices, if, for example, an editor — she cited Arianna Huffington — suddenly wanted everyone to write about sleep.

What happened next was not exactly a scene out of “Norma Rae.” Emily Nussbaum, a television critic, said she would expect to be fired if she wasn’t doing a good job, according to two people there. Nobody was interested in a union rep coming between them and Mr. Remnick on editorial decisions.

Then Ben Taub, an investigative reporter, asked her why Ms. Mohit had told their unionizing colleagues that the NewsGuild was also organizing the writers. When she denied it, he theatrically produced a printed-out screenshot of a WhatsApp message that Ms. Mohit had sent to some 80 of the unionizing employees. In the message, a copy of which I obtained, Ms. Mohit said the union was “in communication” with the writers but could not “be open and public with the fact that we are organizing the staff writers.”

The writers in the room had been invited merely to a meeting to understand what the existing union drive meant for them, Mr. Taub said, and had no sense that they were secretly being organized. He said it was misleading.

“Bluntly, re: NewsGuild, what it comes down to for me is that I would never hire an agent who had lied to or about me,” Mr. Taub wrote to a WhatsApp group for staff writers after the incident. (The NewsGuild’s president, Susan DeCarava, said in response to questions about the exchange that it “does not comment on confidential organizing conversations.”)

The meeting’s host, Adam Davidson, had already been among the writers talking to Mr. Remnick about setting up a health care plan for writers. He summarized what he saw as the “consensus view” in another WhatsApp message to colleagues. (The contents of the writers’ group messages were shared with me on the condition I only quote people by name with their permission. Some of the material in this article is also drawn from reporting on this topic by my colleagues Noam Scheiber and Marc Tracy.)

“None of us want to do anything that could jeopardize the magazine we love. We don’t want so strong a union that mediocrity reigns and it’s impossible to get rid of poor performers. We actually kind of like the feeling that we need to continue to earn our place,” wrote Mr. Davidson, who is no longer a staff writer but still contributes to The New Yorker. “BUT, most of us would like to be able to get health insurance.”

The unionization effort has created an uncomfortable moment for the writers at The New Yorker, who have the kind of jobs and influence every journalist wants but few attain. It has set off reflections on their status and revealed the rare bond and unusual deference many of them feel toward Mr. Remnick.

About a month after the meeting at Mr. Davidson’s apartment, about 40 of the writers met in the community room at a West Village apartment building. The gathering was, many noted, probably the first time that so many of the magazine’s scattered staff members had ever been in one room, and someone invited the Magnum photographer Peter van Agtmael to document it. Jane Mayer came from Washington, and Lawrence Wright flew in from Austin, Texas. They sat in a big circle and, like the millennials only a few of them are, shared details of their own compensation arrangements.

The conversation made clear how inconsistent benefits and pay were among writers, and many left angry at Condé Nast over the opaque and uneven system. But they were also suspicious of the NewsGuild, and began a parallel set of meetings with its rival, the Writers Guild of America, East.

Neither effort has gained traction.

Many of the writers, it seemed, valued their independent contractor status. Some, led by Tad Friend and Jia Tolentino, used the threat of a union — and the suggestion that Condé Nast had illegally classified many of them as contractors, which the company disputes — to set up a process by which some writers could become employees with health benefits. A deal was finalized late last month.

And that has left the most prominent writers mainly watching from the sidelines in recent weeks as a bitter labor dispute has consumed their beloved magazine. The New Yorker is now working out the final details of a contract, and people on both sides appeared optimistic they would reach an agreement this week. They’ve agreed on a $55,000 starting salary and are hashing out issues like caps on potential health care cost increases, people familiar with the talks said — even as the Guild threatens a strike.

Many writers have tweeted in support. But no writers turned up at a protest outside Condé Nast headquarters on May Day, and none appeared to be present at a march outside the home of Condé Nast’s global chief content officer, Anna Wintour, on June 8.

The conflict has seized the attention of the industry not just because of the employees’ glee at holding the brand hostage in public, but also because it highlights big questions facing contemporary media. How much power can employers exercise over their employees? Are junior employees apprentices or a permanent creative underclass? And as the labor movement seeks to level the playing field, will the stars go along?

It’s all particularly personal at The New Yorker, where the campaign has pitted a culture built on personal relationships and deep trust against a group of employees who reject the idea that they should be subject to the whims of any boss, no matter how benign.

The easiest-to-understand element of the dispute involves the wages of the production employees, the group that includes everyone from fact checkers to social media editors. Some salaries start as low as $42,000 a year, and remain under $60,000 after 20 years on the job.

But other tensions revolve around the sense that the junior jobs only rarely offer promotions into the ranks of writers, and no clear career path.

Neither of these issues is new. In 1976, a group of employees got fed up with flat wages and, among other things, a 50 percent cut to the magazine’s annual psychiatric benefit, and brought in the union (then the Newspaper Guild) to set things right. The editor, William Shawn, responded with pained, elegant letters, warning that collective bargaining would undermine the “friendly, gentle, free, informal, democratic atmosphere” that made The New Yorker special. The employees ultimately backed down, rejecting the notion of unionism for what seemed in part to be cultural reasons.

An editor there, Daniel Menaker, wrote years later that he was “embarrassed about the ineffectuality and yes, ordinariness of the Guild people we’d come in contact with,” but also that Mr. Shawn’s conduct had been revealing — a classic case of liberals “turning to the right when the capitalist chips were down — just as I had been told, from my childhood on, liberals usually do.”

The New Yorker writer Janet Malcolm was asked during a libel case how compensation was set. “By the whim of the editor,” she replied.

These days, however, the NewsGuild has the cultural wind at its back. A labor movement revival began when Gawker employees joined the W.G.A. in 2015 and has continued apace. There’s been nothing like it since the 1930s. (I’ve had a front-row seat to that and continue to at The New York Times, and wrote about the trend last year.)

And unlike organizers in the 1930s, the NewsGuild has social media. It never rains on a Twitter picket line. Writers who are skeptical of the union’s tactics — some told me they object to its confrontational social media style — have bitten their tongues or deleted critical tweets. In one recent Zoom call, writers even complained to Mr. Remnick of their fears of being bullied on Twitter if they diverge from union talking points.

And underlying much of the 2021 labor tensions are political tensions. The younger generation of employees is to the left of its elders on issues of substance. The New Yorker’s union, for instance, tweeted and then deleted its “solidarity with Palestinians from the river to the sea,” a phrase that some interpret as threatening violence.

Virtually all of The New Yorker writers I spoke to said they supported the union’s core economic goals, and believed the junior staff members deserve pay increases. The union includes 120 people and there are about the same number of staff and contributing writers. Many, including Ms. Nussbaum and Ms. Mayer, have spoken out in favor of the union’s current posture. But some also shun its blunt and adversarial language.

Some of the writers are also worried about the impact of a strike. On one recent Zoom call with union leaders, Mr. Wright, a former Teamster and longtime W.G.A. member, warned that a strike could last months and do immense damage.

But many writers also see what The New Yorker offers as a good deal: a prestigious place to publish that allows them to retain the rights to their work. It’s also a gateway into the real money — books, movies, speaking gigs or other opportunities in the broadening economic landscape for brand-name writers. Those opportunities now also include newsletter platforms like Substack, and a new start-up called Puck, a digital magazine in which star writers get a cut of the subscription business and a share of the company.

That dynamic poses a threat to both traditional, top-down media institutions and organized labor.

While the union won headlines by marching to Ms. Wintour’s house, which was guarded, disappointingly, by two low-key men in shapeless cotton shirts, Ms. Wintour has no real involvement in The New Yorker. Mr. Remnick reports directly to Condé Nast’s chief executive. He’s in a strong position. The magazine was once a charity case among flush glossies, but its subscription business, which boomed in the Trump years, has given its editor unique leverage: The New Yorker avoided companywide layoffs last year, and has also been left out of the rest of Condé Nast’s painful drive toward centralization.

Mr. Remnick declined to be interviewed, but said in an email that his two goals were “that we achieve our highest editorial ambitions and that we work together with fairness,” adding, “I’ll be glad to see us sign a foundational contract that memorializes our commitment to both.”

Many of the writers I spoke to said they saw Mr. Remnick as caught between an uncompromising union and an ailing parent company. Union activists tend to be less charitable, and feel he’s trying to have it both ways. Gili Ostfield, a production employee and union member, pointedly told HuffPost last week that if The New Yorker tries to print a diminished magazine without striking employees, it will be “a stain on David Remnick’s reputation.”

But the support Mr. Remnick retains among the signature writers is deep. Many talk of him as an adored, slightly feared and somewhat distant father whose approval they always seek. They also have deep confidence in his ability to make their work better.

The moment, of course, seems all the stranger, in that much of the conflict is playing out virtually, while everyone is working remotely.

Mr. Remnick has told some writers that he is simply eager for the conflict to be resolved. The editor, who is 62, has also said he doesn’t plan to follow the example of William Shawn, who ran the magazine until he was nearly 80 and the institution had become a kind of museum of itself.

He has tried to be reassuring, even as the prospect of putting out the print magazine without editorial staff members looms. No matter what happens, Mr. Remnick told writers on one recent Zoom call, he would not ask them to cross virtual picket lines.

Correction: June 13, 2021

An earlier version of this article misidentified a New Yorker writer who attended a meeting to discuss union issues, and who has spoken in favor of the union’s posture. She is Jane Mayer, not Jane Kramer.