Controversy grew on Wednesday over tweets from Elon Musk engaging with criticism of Twitter employees, despite a promise from the entrepreneur not to “disparage” the company or its representatives while he completes the deal to acquire the social media platform. The world’s richest man agreed to restrictions on his tweets as part of a 95-page agreement covering his $44bn acquisition filed on Tuesday. However, a day after signing the agreement, which was published on the website of the US securities regulator, Musk responded to tweets from two political commentators that criticised Twitter staff. Musk replied on Tuesday night to a Twitter post from the podcast host Saagar Enjeti flagging an article claiming Twitter’s legal head, Vijaya Gadde, had become “emotional” during a meeting to discuss the deal. In the post, Enjeti referred to Gadde as Twitter’s “top censorship advocate”, in a reference to the company’s decision in 2020 to block sharing of a New York Post story about President Joe Biden’s son Hunter. Musk replied: “Suspending the Twitter account of a major news organisation for publishing a truthful story was obviously incredibly inappropriate.” His intervention triggered negative tweets from users about Gadde, including one quote tweet in response stating that she would “go down in history as an appalling person”, while other posts called for her to lose her job. Musk also replied to a potentially defamatory tweet from the rightwing commentator Mike Cernovich about Twitter’s deputy general counsel, Jim Baker, which referred to Baker’s work in a previous role at the FBI. Replying, Musk wrote: “Sounds pretty bad …” Former Twitter CEO Dick Costolo responded to Musk’s comments on Twitter on Wednesday, calling out the CEO for bringing on “harassment and threats” to Gadde. Costolo added: “Bullying is not leadership”. Twitter CEO Parag Agrawal tweeted shortly after: “I took this job to change Twitter for the better, course correct where we need to, and strengthen the service. Proud of our people who continue to do the work with focus and urgency despite the noise.” Twitter has been approached for comment. Eleazer Klein, a partner at US law firm Schulte Roth and Zabel, said Musk’s tweets would not have come as a surprise to the company despite the agreement. He said: “The fact that he would be vocal about his beliefs cannot come as a surprise to the company or be unanticipated. You would imagine that the company will be thoughtful about what is really an issue in this case for the deal moving forward.” The agreement also stated Musk would have to pay Twitter $1bn if he walks away from the deal. The break clause, a common feature of takeover agreements, would be triggered if the financing for the deal falls apart. Twitter will also have to pay a $1bn fee to the entrepreneur if, for instance, it accepts a higher bid from elsewhere. Musk has put together a $46.5bn funding package for the deal and his own contribution to it has concerned investors in Tesla, who wiped $126bn off the company’s value on Tuesday amid worries that the billionaire may have to sell shares in the electric carmaker to fund his share. Musk is part-funding the Twitter deal with $21bn of his own equity and a further $12.5bn loan secured against his Tesla stake. The document filed with the US financial watchdog also addresses Musk’s penchant for attention-grabbing tweets that are avidly consumed and retweeted by his 86 million followers. The agreement states: “The equity investor shall be permitted to issue tweets about the merger or the transactions contemplated hereby so long as such tweets do not disparage the company or any of its representatives.” According to the US dictionary publisher Merriam-Webster, the legal definition of disparagement is: “the publication of false and injurious statements that are derogatory of another’s property, business, or product”. Hours later, Musk tweeted that Truth Social, Donald Trump’s rival social media platform, was outperforming Twitter and TikTok on the Apple store. Also on Wednesday, a US district judge denied Musk’s request to scrap a settlement with the US securities and exchange commission (SEC) over 2018 tweets in which the CEO claimed he had funding to take Tesla private. That settlement required Musk’s tweets regarding Tesla to be approved by a company attorney. The judge also denied a motion to nullify subpoenas in an investigation into whether Musk violated the settlement last November.