Elon Musk had plans to buy Twitter and rescind its content moderation policies. On Tuesday, just a day after reaching his $44 billion deal to buy the company, Mr. Musk was already busy working on his agenda. He tweeted that previous moderation decisions by a top Twitter lawyer were “obviously incredibly inappropriate.” He later shared a meme mocking the lawyer, which sparked a spate of attacks from other Twitter users.

Mr. Musk’s personal criticism was a crude reminder of what faces staff who create and enforce Twitter’s complex moderation policies. His vision for the company would take it right back to where it started, employees said, forcing Twitter to relive the past decade.

Twitter executives who created the rules said they previously held views about online language similar to Mr Musk’s. They felt that Twitter’s policies should be limited and mimic local laws. But more than a decade of grappling with violence, harassment and vote-rigging have changed their minds. Today, many executives at Twitter and other social media companies see their content moderation policies as essential safeguards to protect the expression of opinion.

The question is will Mr. Musk change his mind when confronted with the darkest corners of Twitter.

“You said you want more ‘free speech’ and less moderation on Twitter. What does that mean in practice?” Twitter staffers wrote an internal list of questions they wanted to ask Mr. Musk, which was seen by the New York Times.

Another question read: “Some people interpret your arguments in defense of free speech as a desire to reopen the floodgates to harassment. Is that true? And if not, do you have any ideas on how to both improve freedom of speech and keep the door closed to harassment?”

Mr Musk has been unperturbed by warnings that his plans are misguided. “The extreme antibody response from those who fear freedom of expression says it all,” he tweeted Tuesday.

He went on to criticize the work of Vijaya Gadde and Jim Baker, two of Twitter’s top attorneys. Ms. Gadde has led Twitter’s policy teams for more than a decade and has often made complicated moderation decisions, including the decision to impeach Donald J. Trump near the end of his term as president. Mr. Baker, former General Counsel of the FBI, joined Twitter in 2020.

Twitter CEO Parag Agrawal didn’t directly respond to the criticism, but in a tweet he wrote: “Proud of our people who continue to do their jobs with focus and urgency despite the noise.”

Officials at Twitter and other social media companies said that Mr. Musk seemed to understand little about Twitter’s approach to content moderation and the problems that had led to its rules — or that he simply didn’t care. Some of the suggestions he made, like flagging automated accounts, were in place before Mr. Musk made his offer.

“He’s basically buying himself the position of rule-maker and public speaker,” said David Kaye, a law professor at the University of California, Irvine who has worked with the United Nations on public speaking. “It was really exhausting for everyone who was in that position.”

In its early years as a small start-up, Twitter was guided by one philosophy: The tweets need to flow. That meant Twitter did little to moderate conversations on its platform.

The founders of Twitter took their cues from Blogger, Google’s publishing platform, which several of them helped build. They believed any objectionable content would be countered or drowned out by other users, said three employees who worked at Twitter during the period.

“They have a level of idealistic zeal: ‘If people just embrace it as a platform for self-expression, amazing things will happen,'” said Jason Goldman, who was on Twitter’s founding team and has served on Twitter’s board of directors. “This mission is valuable, but it blinds you to the assumption that certain bad things that happen are mistakes rather than equal uses of the platform.”

The company typically removed content only if it contained spam or violated US laws prohibiting child exploitation and other criminal activities.

In 2008, Twitter hired Del Harvey, its 25th employee and the first person tasked with the task of full-time content moderation. The Arab Spring protests began in 2010 and Twitter became a megaphone for activists, reinforcing the belief of many workers that good language would prevail online. But the power of Twitter as a tool for harassment was demonstrated in 2014 when it became the epicenter of Gamergate, a mass harassment campaign that inundated women in the video game industry with death and rape threats.

“If there are no rules against abuse and harassment, some people run the risk of being silenced and then you can’t benefit from their voice, their perspective, their free expression,” said Colin Crowell, former head of Twitter of global public policy, who left the company in 2019.

In response, Twitter began expanding its policies. But new threats emerged. In September 2016, a Russian troll farm was quietly established 2,700 fake Twitter profiles and used them to sow discord between Mr. Trump and Hillary Clinton over the upcoming presidential election.

The profiles went undetected for months while complaints of harassment continued. In 2017, then-CEO Jack Dorsey stated that policy enforcement would become the company’s top priority. Later that year, women boycotted Twitter during the #MeToo movement, and Mr Dorsey acknowledged the company “still isn’t doing enough”.

He announced a list of content the company no longer tolerates: nude photos shared without the subject’s consent, hate symbols and tweets glorifying violence.

In 2018, Twitter suspended several accounts related to the hack-and-leak operation that exposed Mrs Clinton’s campaign emails and began suspending right-wing figures such as Alex Jones from his service for repeatedly violating policies.

The next year, Twitter instituted new policies aimed at preventing the spread of misinformation in future elections, and banned tweets that might discourage people from voting or mislead them about how to do so. Mr Dorsey banned all forms of political advertising but often left difficult moderation decisions to Ms Gadde.

Twitter also devised a strategy that would allow it to maintain more tweets: instead of removing them, it attached labels to tweets that contained misinformation about elections, limiting their ability to spread quickly across the platform.

In preparation for the 2020 US presidential election, Twitter banned manipulated videos known as “deepfakes” and prohibited users from sharing material obtained through hacking campaigns.

This policy was tested when the New York Post ran an article that contained emails purported to have come from Joseph R. Biden Jr.’s son, Hunter’s laptop. Fearing that the materials came from a hack-and-leak operation, Twitter blocked the article from being published on its platform.

Mr. Dorsey publicly disagreed with this decision. Days later, Ms Gadde announced the policy had changed and Twitter would allow the Post article to appear in tweets.

The episode has become a fulcrum in conservative criticism of Twitter and has echoed in Mr Musk’s criticism of Ms Gadde.

Mr Musk said he wanted to take Twitter back to its beginnings, when only illegal content was removed. “I am against censorship that goes well beyond the law,” Mr Musk tweeted on Tuesday.

Mr Musk’s plans could also face legal problems in Europe. European politicians agreed on this on Saturday landmark legislation called the Digital Services Actcalling for social media platforms like Twitter to more aggressively monitor their services for hate speech, misinformation and illegal content.

The new law will oblige Twitter and other social media companies, with more than 45 million users in the European Union, to conduct annual risk assessments of the spread of harmful content on their platforms and outline plans to combat the problem. If they don’t do enough, companies can be fined up to 6 percent of their global turnover or even banned from the European Union for repeated violations.

Inside Twitter, frustration over Mr. Musk’s moderation plans has risen, with some staffers wondering if he really would stop working at such a critical moment when they are supposed to start tweeting about elections in Brazil and another national election in the United States to moderate states.

Adam Satariano contributed reporting.

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