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A decade ago, Twitter executives, including the chief executive, Dick Costolo, declared that the social media site was the “free-speech wing of the free-speech party.” The stance meant Twitter would defend people’s ability to post whatever they wished and be heard by the world.

Since then, Twitter has been dragged into morasses over disinformation peddlers, governments’ abuse of social media to incite ethnic violence and threats by elected officials to imprison employees over tweets they didn’t like. Like Facebook, YouTube and other internet companies, Twitter was forced to morph from hard-liner on free expression to speech nanny.

Today, Twitter has pages upon pages of rules prohibiting content such as material that promotes child sexual exploitation, coordinated government propaganda, offers of counterfeit goods and tweets “wishing for someone to fall victim to a serious accident.”

The past 10 years have seen repeated confrontations between the high-minded principles of Silicon Valley’s founding generation of social media companies and the messy reality of a world in which “free speech” means different things to different people. And now Elon Musk, who on Monday struck a deal to buy Twitter for roughly $44 billion, wades directly into that fraught history.

Successive generations of Twitter’s leaders since its founding in 2006 have learned what Mark Zuckerberg and most other internet executives have also discovered: Declaring that “the tweets must flow,” as the Twitter co-founder Biz Stone wrote in 2011, or “I believe in giving people a voice,” as Mr. Zuckerberg said in a 2019 speech, is easy to say but hard to live up to.

Soon, Mr. Musk will be the one confronting the gap between an idealized view of free speech and the zillion tough decisions that must be made to let everyone have a say.

His agreement to buy Twitter puts the combative billionaire, who is also the chief executive of Tesla and SpaceX, at the white-hot center of the global free-speech debate. Mr. Musk has not been specific about his plans once he becomes Twitter’s owner, but he has bristled when the company has removed posts and barred users, and has said Twitter should be a haven for unfettered expression within the bounds of the law.

“Free speech is the bedrock of a functioning democracy, and Twitter is the digital town square where matters vital to the future of humanity are debated,” Mr. Musk said in a statement announcing the deal.

Mr. Musk is a relative dilettante on the topic and hasn’t yet tackled the difficult trade-offs in which giving one person a voice may silence the expression of others, and in which an almost-anything-goes space for expression might be overrun with spam , nudity, propaganda from autocrats, the bullying of children and violent incitements.

“We need to protect freedom of speech in order to make our democracy work,” said Jameel Jaffer, the executive director of the Knight First Amendment Institute at Columbia University. “But there is a lot of distance to cover from that premise to the kinds of decisions that social media companies have to make every day.”

Almost no place on the internet or in the physical world is a zone of absolute free expression. The challenge of online expression is the challenge of expression, period, with questions that have few simple answers: When is more speech better, and when is it worse? And who gets to decide?

In countries with strong courts, civic groups and news media to hold politicians accountable, it may be relatively benign when elected leaders trash talk their opponents online. But in countries such as Myanmar, Saudi Arabia and Somalia, government leaders have weaponized social media to subject their critics to releaseless verbal harassment, to spread that mostly unchecked or to incite ethnic violence lies.

If Twitter wants to pull back from moderating speech on its site, will people be less willing to hang out where they might be harassed by those who disagree with them and swamped by pitches for cryptocurrency, fake Gucci handbags or pornography?

The 2016 US presidential election and the Brexit vote that same year gave Silicon Valley executives, US elected officials and the public a peek what can go wrong when social media companies opt not to wade too deeply into what people say on their sites. Russian propagandists amplified the views of deeply divided Americans and Britons, further polarizing the electorate.

During Mr. Trump’s presidency — particularly in the early months of the coronavirus pandemic and then as Mr. Trump and his supporters spread false claims about voter fraud in the 2020 election — Twitter, Facebook and YouTube changed their tune about the role they played in fanning anger, lies, distortions and division that left some people feeling exhausted and cynical about the world around them .

Twitter and Facebook, pressured at times by their employees, took more steps to pull down or label posts that might break their rules against false information and tinkered with computer systems to suppress viral lies from spreading far and fast. Facebook, Twitter and YouTube also kicked Mr. Trump off their platforms after the Capitol riot of Jan. 6, 2021.

It was a crossing-the-Rubicon moment when the “tweets must flow” crowd acknowledged that it could and should do more to prevent people from using its internet properties to blare information that could mislead or harm others.

Some of the judgment calls from Twitter and its peers might have been speech-control overreach. Now more governments around the world are forcing social media companies to shift from largely self-regulating online expression to following government-enforced rules.

New laws, including the Digital Services Act in the European Union, require Twitter and its peers to do more to scrub their sites of misinformation and abuse. In other countries, such as Vietnam, social media companies risk legal jeopardy when people post what the government deems unflattering criticisms of it. Twitter and other social media companies are in the position of potentially harming free expression and democracy when they intervene too little in what people post online and when they intervene too much.

Kate Klonick, an assistant professor at St. John’s University School of Law, said growing laws over online expression theoretically took some power over speech away from unelected Silicon Valley executives. But those leaders still must decide on the interpretation of the laws and make decisions on the speech ungoverned by them.

There is no getting around the fact that Mr. Musk will join Mr. Zuckerberg, Google’s Sundar Pichai, TikTok’s Shouzi Chew and Apple’s Tim Cook as the handful of corporate executives who have enormous say over granting oring access to platforms of denying global discourse.

One of the paradoxes of the Silicon Valley revolution is that it disempowered old gatekeepers of information and persuasion such as media tycoons and political leaders but created new ones. Mr. Musk’s purchase of Twitter won’t change that. We may not want these digital media barons to have so much power, but the reality is that they do.

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