How Elon Musk, Jack Dorsey, and Parag Agrawal cratered the Twitter deal, in texts

Elon Musk’s deposition for the Twitter v. Musk suit may have been rescheduled for next week, but the public got some more inside dirt about his plans for Twitter, thanks to the release of two slideshow presentations and a slew of Musk texts.

The texts show Musk and a variety of contacts — including former Twitter CEO Jack Dorsey, entrepreneur Jason Calacanis, and podcaster Joe Rogan — talking about everything from the blockchain to putting Oprah on Twitter’s board. (That part might be a joke, but with Musk, it’s difficult to tell.) But above all, they’re a chronicle of the deal’s slow implosion.

The texts are light reading, and you can check them out here if you’re so inclined. They’re mostly divided into two sections: a giddy feeding frenzy around Musk acquiring Twitter and a protracted venting session as the acquisition went south.

The first key section starts about a month before Musk’s $44 billion offer to buy Twitter. In March of 2022, Jack Dorsey reaches out about one of Musk’s tweets, part of a thread complaining about a lack of free speech on Twitter. “A new platform is needed. It can’t be a company. This is why I left,” Dorsey says. He tries to sell Musk on a new decentralized communication protocol, saying Twitter “never should have been a company.” Musk more or less agrees, but with a caveat: “I think it’s worth both trying to move Twitter in a better direction and doing something new.”

Dorsey expresses doubts about this, but when Musk buys a substantial share in Twitter, Dorsey is extremely on board. “I’ve wanted it for a long time. Got very emotional when I learned it was finally possible,” he texts after an initial announcement that Musk is getting appointed. He’s equally enthusiastic about Musk meeting current CEO Parag Agrawal: “Parag is an incredible engineer.”

Threaded through various text message subplots (Kimbal Musk really wants to talk with Elon about Web3), one theme stands out: as Twitter’s old CEO pushed to bring Twitter and Musk together, Musk’s patience with its new one frayed almost immediately. Musk and Dorsey are on the same high-minded wavelength. Meanwhile, Agrawal comes off as, well, a current executive and former nuts-and-bolts engineer at a very large company that’s about to take a big risk.

This isn’t immediately an issue. “I just want Twitter to be maximum amazing,” Musk gushes in an early conversation after his investment, touting his expertise in “heavy duty software.” Agrawal tries gamely to do a little coder-to-coder bonding: “I used to be CTO and have been in our codebase for a long time … treat me like an engineer instead of CEO and let’s see where we get to.”

But two days later, Agrawal makes a pivotal mistake: he asks Musk to stop tweeting. “You are free to tweet ‘is Twitter dying?’ or anything else about Twitter — but it’s my responsibility to tell you that it’s not helping me make Twitter better in the current context,” Agrawal texts on April 9th. “I’d like the company to get to a place where we are more resilient and don’t get distracted, bu we aren’t there right now.” Two minutes later, Musk declares joining the board “a waste of time” and says he’ll offer to take Twitter private. (Over in the Web3 B-plot, he’s simultaneously texting Kimbal about how to start a paid blockchain social network.)

“Fixing Twitter by chatting with Parag won’t work,” he tells Twitter board chair Bret Taylor tersely. “Drastic action is needed.”

(Meanwhile, in an ongoing C-plot that is by far the most entertaining part of these text messages, Jason Calacanis offers Musk a constant stream of thirsty suggestions that include raising his offer price, moving Twitter’s headquarters to the Gigafactory in Texas, and bringing YouTube creator MrBeast onto Twitter to win over Zoomers and Millennials. Also, Calacanis is ride-or-die for Musk, will jump on a grenade for him, and tells Musk, among other things, “You have my sword,” and “Twitter CEO is my dream job.”)

Dorsey is entirely on board with the acquisition — “I won’t let this fail and will do whatever it takes. It’s too critical to humanity,” he pledges. (Back in the B-plot again, Musk is texting Boring Company CEO Steve Davis about “a blockchain-based version of Twitter” where users pay in Dogecoin, then thankfully concluding that “blockchain Twitter isn’t possible.”) And Dorsey tries to smooth things over with Musk and Agrawal: “He is really great at getting things done when tasked with specific direction,” Dorsey tells him.

Musk is not into this. “Parag is just moving far too slowly and trying to please people who will not be happy no matter what he does,” he says. Dorsey diplomatically takes the glass as half-full, saying that “at least it became clear that you can’t work together.” But it’s the last message we get from him — while Musk texts Rupert Murdoch heirs Kathryn and James to say he’s too busy with his crypto startup to rejoin Twitter.

And this all happens while Musk is still mostly excited about buying Twitter. (This section ends perfectly with venture capitalist Steve Jurvetson suggesting that Musk hire his son to run operations — again, a feeding frenzy.) Jump into May, and he’s complaining to banker Michael Grimes about Twitter having “asked no good questions and had no good comments” at a meeting, immediately before asking to slow the deal down in case of World War III and guessing that fewer than half of Twitter’s users are real.

There was plenty of obvious public friction between Musk and Agrawal, and Dorsey’s support for the acquisition was known as well. But based on the string of text messages here, it’s striking just how quickly things with Agrawal go south and how little Dorsey manages to sell Musk on any of this being a good idea — something Musk seems to start doubting nearly the minute he strikes his bargain.