Trump’s attempt to ban TikTok and WeChat could face legal trouble for infringing on free speech, according to a First Amendment expert

President Donald Trump signs the National Defence Authorization Act for Fiscal Year 2020 at Andrews Air Force Base, Md., Friday, Dec. 20, 2019. Andrew Harnik/AP

After weeks of ramping up his rhetorical attacks on TikTok, President Donald Trump issued an executive order Thursday banning “any transactions” with its parent company ByteDance.

He didn’t stop there, issuing a second order shortly after targeted at transactions with Tencent-owned messaging app WeChat.

In both cases, Trump cited concerns that the apps could allow the Chinese government to spy on Americans and claiming that Beijing could pressure the companies to censor content it doesn’t like.

But attempting to censor free speech is the exact reason Trump’s executive orders could run into legal trouble in US courts, according to one legal expert.

Kyle Langvardt, a law professor at the University of Nebraska Lincoln, told Business Insider that Trump’s orders “are likely to have First Amendment problems.”

“The reason is that they discriminate based on the identity of the speaker (Bytedance, Tencent), and also, arguably, based on the ‘content’ of their speech,” Langvardt said.

In Thursday’s orders Trump invoked his authority the International Emergency Economic Powers Act, a 1977 law that allows him to declare a national emergency, during which he has “broad authority” to regulate foreign economic transactions.

In an executive order implemented last year, Trump used the IEEPA to give the administration the ability to interfere in any business transaction involving “information and communications technology or services” that “otherwise pose an unacceptable risk to the national security of the United States or the security and safety of United States persons.”

Langvardt said that “both orders probably comply with the IEEPA,” but they still could face legal scrutiny for discriminating against certain speakers or types of speech.

“Content discrimination is unconstitutional unless the law is ‘narrowly tailored’ to serve a ‘compelling governmental purpose,'” he said. “Most laws fail this test.”

Langvardt added that, though he doesn’t personally buy this interpretation, most First Amendment experts would consider the apps themselves to be “content,” and therefore targeting TikTok and WeChat specifically is effectively discriminating against them in violation of the First Amendment.

“The companies express themselves by setting their own rules for what to take down and what to leave up,” he said, so “the [executive orders] discriminate against their ‘message.'”

Aside from the legality of Trump’s orders, there are also practical and technical considerations.

Langvardt and other legal experts told Business Insider that approaches such as removing the apps from Apple and Google’s app stores or blocking internet traffic to the apps similar to China’s “Great Firewall” both raise significant challenges of their own.

Short of a ban that effectively prevents Americans from using TikTok, Trump has pushed instead for a US company to buy ByteDance’s share in the company, thereby severing its Chinese connections.

Right now, Microsoft appears to be the leading contender. The Seattle-based tech giant said earlier this month it’s in talks with ByteDance, and Trump said he would be open to a Microsoft purchase due to the company’s existing “high-level” security clearances.