Musk then sent out another picture of a fake tweet written by him, which read “Now I’m going to buy McDonald’s and fix all of the ice cream machines,” captioning the image with “Listen, I can’t do miracles ok.”

After pledging $21 billion in equity and raising $25.5 billion of debt and margin loan financing, Musk has continued to use Twitter to buff his image as a brash billionaire who is not afraid to break the rules of polite society. But as Musk jokes around about the immense power and influence he has over markets and huge corporations, investors in Twitter may not be on the same page.

Twitter’s stock is currently trading 11% below Musk’s $54.20 offer price, a large drop for a deal that is likely to see little antitrust pushback—indicating that investors might be anticipating a breakdown of the deal in its current structure.  

Shares in Tesla have fallen more than 25% since Musk first bought a 10% stake in Twitter on Apr. 4, with market watchers fearing Musk may not have enough cash sitting around to fund the Twitter purchase and will sell Tesla shares to fund the project.

And if investor doubt wasn’t enough to make Musk second-guess the acquisition—which would cost him $1 billion to back out of—Musk may have also gotten a taste of what his “free speech” platform looks like after his tweet on the company’s legal policy chief Vijaya Gadde was met with racist and sexist vitriol.

Troublesome tweets

A day after an SEC filing said Musk must avoid posting disparaging tweets about Twitter and its agents until the buyout deal is finalized, Musk tweeted a meme on Wednesday mocking the company’s head of legal, policy, and trust, Vijaya Gadde.

Gadde, formally Jack Dorsey’s right hand, has been the main driver of Twitter’s new rules regulating the content of its users. Gadde was behind the company’s decision to ban political ads, kick Donald Trump off the platform, and delete controversial COVID-19 tweets. The changes she made at Twitter have rippled through Silicon Valley, with Spotify suspending political ads two months after Twitter did and Reddit also cracking down on hate speech.

But during the 2020 U.S. elections, there was an error in Twitter’s censorship, which Gadde was responsible for. Twitter censored a New York Post story about the contents of Hunter Biden’s laptop, doubting the sources of the story and believing it to possibly be part of a disinformation campaign by Russian intelligence. The story later turned out to be true and verified by multiple other news organizations.

“Suspending the Twitter account of a major news organization for publishing a truthful story was obviously incredibly inappropriate,” Musk tweeted back to YouTuber Saagar Enjeti on Apr. 26, referencing but not naming Gadde. Musk was responding to Enjeti’s post about a Politico story where Twitter’s “top censorship advocate” allegedly cried during the meeting discussing Musk’s acquisition.  

A day later, Musk tweeted a meme of an imaginary conversation between Gadde and Youtube host Tim Pool talking about Twitter’s left-wing bias. The conversation circles a logo of The Joe Rogan Experience, which was also recently slammed for spreading COVID-19 misinformation.   

As soon as Musk tweeted out the image, a flood of racist and sexist comments were directed at the Indian-born Gadde on the platform. Users blamed her for having “destroyed countless @Twitter accounts for speaking the truth.” Most abusive tweets were later removed for violating Twitter rules.

Jason Goldman, a member of Twitter Inc.’s founding team and former board member, said on Bloomberg TV, “You absolutely should not allow the prospective owner of the company to troll your employees for the decisions that they made.”

Goldman criticized Elon Musk’s plan to relax speech restrictions on the platform, adding it “reveals a very naive, unserious approach to the content moderation issues he will face.”