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An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

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An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

An hour in the Oval Office with President Trump Fortune Editor-in-Chief: Alyson Shontell sat down with President Trump in the Oval Office for an hour. Tariffs, Intel, AI, Boeing, Iran—and the question every CEO eventually has to answer: who's next?

TechElon Musk

Elon Musk doubted ex-Twitter CEO Parag Agrawal from the start because he was too nice: ‘What Twitter needs is a fire-breathing dragon’

Nicholas Gordon
By
Nicholas Gordon
Nicholas Gordon
Asia Editor
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Nicholas Gordon
By
Nicholas Gordon
Nicholas Gordon
Asia Editor
Down Arrow Button Icon
September 1, 2023, 6:37 AM ET
Twitter (now X) owner Elon Musk
Elon Musk’s changing relationship with then–Twitter CEO Parag Agrawal is charted in a new biography from author Walter Isaacson.Joel Saget—AFP/Getty Images

One of the first things Elon Musk did after taking over Twitter—which the billionaire has since renamed X—was fire several of Twitter’s senior leaders, including then-CEO Parag Agrawal, “for cause.” It capped a fractious relationship between the two business leaders since Musk first expressed his intention to buy the social media company in April last year.

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Yet Musk was wary of Agrawal from their very first meeting—namely, because he thought the social media CEO was far too likable, according to an excerpt from author Walter Isaacson’s upcoming biography of the controversial billionaire, published in the Wall Street Journal. 

“What Twitter needs is a fire-breathing dragon, and Parag is not that,” Musk said after a dinner between the two with Twitter board chair Bret Taylor on Mar. 31, 2022. The covert meal was organized soon after Musk revealed he was Twitter’s largest shareholder. 

While he called Agrawal “a really nice guy,” Musk preferred tougher CEOs who didn’t care about being liked, according to Isaacson. 

Musk’s view of Agrawal quickly soured after Twitter’s CEO politely suggested it might be better if Musk stopped disparaging Twitter, such as posting, “Is Twitter dying?” 

“It’s my responsibility to tell you that it’s not helping me make Twitter better in the current context,” Agrawal texted Musk in April 2022. 

The billionaire did not take it well. “What did you get done this week?” he wrote back, continuing that “this is a waste of my time.”

Musk turned down a seat on Twitter’s board and instead said he would seek to take the company private for $44 billion. “I don’t have confidence in management,” Musk said in a stock filing around the time he made the offer. 

Twitter soon agreed to Musk’s terms, yet the billionaire quickly got cold feet. Musk said that he should get a discount on buying Twitter, arguing that executives like Agrawal had falsified the number of bots on the platform.

Twitter sued Musk to force him to close the deal, and the billionaire eventually agreed to buy the company at the original price after lawyers convinced him he was likely to lose. Musk soon became enthusiastic about buying Twitter again, telling Isaacson in September 2022 there were “many things I could fix” at Twitter, and disparaging the company’s then-leaders as “blockheads and idiots.” 

Musk’s relationship with Twitter executives, at that point, was irreparable. Musk brought forward the close of his Twitter acquisition by several hours so he could fire executives like Agrawal before their stock options could vest. “There’s a 200-million differential in the cookie jar between closing tonight and doing it tomorrow morning,” Musk told Isaacson at the time.

Musk felt the ruthless move was justified owing to a continued belief that Twitter executives had misled him. Immediately after closing the deal, he terminated Agrawal, who was escorted from the building minutes later. “We beat him,” wrote Musk’s lawyer, Alex Spiro, at the time.

Twitter did not immediately respond to a request for comment. 

Who is Parag Agrawal?

Agrawal took over as Twitter’s CEO in 2021, after founder Jack Dorsey’s second stint of running the social media company. (In texts to Musk, Dorsey praised Agrawal as an “incredible engineer.”)  Before that, Agrawal served as Twitter’s chief technology officer. 

Upon taking over the company, Musk also fired Vijaya Gadde, Twitter’s then-head of legal, policy, and trust. Gadde was a focal point for right-wing commentators angry with her content moderation decisions, and Musk had accused her as representing “Twitter’s left-wing bias.” 

Musk also fired Twitter chief financial officer Ned Segal and general counsel Sean Edgett.

Agrawal, along with Gadde and Segal, sued the social media company in April, demanding it pay for legal expenses incurred when the three served as company executives. Twitter, now X, has reportedly refused to pay fees and invoices in a bid to preserve cash.

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About the Author
Nicholas Gordon
By Nicholas GordonAsia Editor
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Nicholas Gordon is an Asia editor based in Hong Kong, where he helps to drive Fortune’s coverage of Asian business and economics news.

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