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Billionaire Elon Musk, CEO of Tesla and Space X, reached an agreement to purchase Twitter for $44-billion.Justin Sullivan/Getty Images

Elon Musk wants to make Twitter Inc. the world’s destination for unbridled free speech. Neither its business model nor its 229 million regular users may be ready for that.

His pending US$44-billion Twitter purchase is likely to reshape one of the world’s foremost communication tools. Given his self-description as a “free speech absolutist,” he’s widely expected to reconfigure the way the social platform polices content.

Taking a neutral approach to moderating speech is a strategy that has historically allowed misinformation and hate speech to flourish on platforms. That’s problematic for advertisers.

“No matter how you slice it, this is bad news for people in the marketing and advertising world – because if there’s one thing advertisers do not like, it’s instability or unpredictability,” says Tod Maffin, who runs the digital agency engageQ in British Columbia and hosts a daily podcast called Today in Digital Marketing. Advertising supplies the vast majority of Twitter’s revenue – bringing the company nearly US$900-million in its most recent quarter.

Opinion: Elon Musk could actually make Twitter better for users – and make money in the process

Many users have threatened to leave Twitter if the Tesla, SpaceX and PayPal entrepreneur relaxes its content approach. “I think he’s going to find out that running Twitter is much harder than wanting Twitter,” says former Twitter engineering leader Leslie Miley. A hands-off approach can drive away more vulnerable users and make platforms less inclusive, rather than more. “The thing about being neutral is that you’re okay with that damage,” he said.

Twitter doesn’t have a great history of keeping dialogue under control. “Twitter was born out of chaos, and companies have a tendency to stick to their DNA,” says Mr. Miley, who was the only Black engineer among Twitter’s leaders when he left the company in 2015. Back then, he says, the company struggled to “authentically” engage in conversations about inclusivity. Mr. Miley says Twitter began to find its footing in recent years in terms of inclusivity and content moderation, but that progress could unwind under Mr. Musk.

“The version of free speech Elon Musk is peddling brings up a fundamental question of power,” says Sonja Solomun, research director at McGill University’s Centre for Media, Technology and Democracy. “Exactly which speech is going to be protected here?”

Usually, Prof. Solomun says, “the people left behind in these conversations are vulnerable communities, like women and racialized groups, who can attest to how they experience harassment and hate speech quite acutely under such free-for-all scenarios.” Mr. Musk has personally left people vulnerable after his tweets. He once called a man who rescued schoolchildren from a cave a “pedo guy,” prompting a long defamation suit that Mr. Musk successfully defended.

And a tweet by Mr. Musk this week about a past moderation decision by Twitter’s legal, policy and trust lead, Vijaya Gadde – to suspend the New York Post over a story about Hunter Biden – led to harassment and threats against her.

With unfiltered speech, “the vast majority of the world’s population” would stay away from a platform, says Mark Weinstein, the founder of MeWe, a social media platform with about 20 million users.

MeWe has built its brand on refusing to censor its users. It’s a philosophy that’s drawn in many people who believe that platforms such as Twitter and Facebook are, indeed, censoring them. “We don’t get involved in political censorship,” Mr. Weinstein says.

But even Mr. Weinstein stops short of the absolutist approach to free speech that Mr. Musk has suggested Twitter could take. “You automatically narrow your market opportunity,” Mr. Weinstein says. If Twitter takes that approach, “they’ll never be able to get advertisers.”

He points out that even platforms with an anti-censorship philosophy, his included, have lines they can’t cross: Threats are threats, violence is violence and the law is the law.

So while MeWe has become widely regarded as a haven for conspiracy theorists and anti-vaccination groups to speak freely, its terms of service still prohibit violence, hate and other hurtful content, which Mr. Weinstein says the company takes seriously. The anti-censorship crowd still goes there, and many pay to subscribe to its ad-free services.

The European Union has already warned Mr. Musk that Twitter will be subject to its stringent content regulations, and it’s difficult to enforce rules on a platform differently across jurisdictions.

Under Mr. Musk, Twitter may also aim to tilt Twitter’s revenue model toward subscriptions, which he suggested in a since-deleted tweet.

Twitter already has a subscription service called Blue, but its revenue is less than one 10th of the amount the company gets from advertising. Based on conversations with people close to the Twitter deal this week, the entrepreneur and analyst John Meyer says he believes Mr. Musk may focus on paid subscriptions as a way to authenticate more real humans on the platform, as opposed to bots he hopes to banish.

But he says he also believes Mr. Musk wants to diversify Twitter’s revenue. “If there’s a recession, the ad business is going to decline,” Mr. Meyer says.

Subscriptions, however, may not solve the philosophical questions at the heart of Mr. Musk’s takeover.

“There is a certain hypocrisy that immediately comes to mind when you think of the fact that he wants more free speech on Twitter, while alluding that he wants to amp up their subscription model,” says Philip Mai, co-director of the Social Media Lab at Toronto Metropolitan University, formerly known as Ryerson University. “Is free speech really free then, or is it just the rich who are able to afford yet another subscription?”

Such a notion challenges Mr. Musk’s conception of Twitter as the world’s “digital town square.” Alfred Hermida, the University of British Columbia professor who wrote the award-winning 2014 book Tell Everyone: Why We Share and Why It Matters, says that reduced content moderation further challenges the town-square concept.

“If Elon Musk believes that a politician should be allowed to present their version of events, because that’s their free speech, then that’s a very different interpretation of what Twitter does,” Prof. Hermida says, “and potentially could really change the Twitter space as sort of this public square, or public utility.”

With reports from Mahdis Habibinia and Michelle Carbert