Jack Dorsey and Elon Musk’s tech bromance takes another weird turn

The relationship between Elon Musk and Jack Dorsey is such an on-again, off-again event that it seems like something out of a television sitcom. And after criticizing Musk’s leadership of Twitter just last year, Dorsey seemed to throw his weight behind that platform over the weekend.

Dorsey, on Saturday, announced (in a one-word reply to someone else’s tweet) that he had departed the board of Bluesky, the Twitter-alternative social media outlet he helped start back in 2019. (That project was originally part of Twitter, but split off on its own before Musk bought Twitter’s assets.) A couple hours later, he seemingly endorsed X, calling it “freedom technology.”

Dorsey, of course, is one of the founders of Twitter and was its longtime CEO. He’s also cofounder of Square-parent Block, where he returned as CEO last September. 

Bluesky confirmed Dorsey’s departure Sunday, saying, “We sincerely thank Jack for his help funding and initiating the Bluesky project. Today, Bluesky is thriving as an open source social network. . . . With Jack’s departure, we are searching for a new board member for the Bluesky public benefit company who shares our commitment to building a social network that puts people in control of their experience.”

Bluesky has an enthusiastic user base, but it’s still a small one, compared to its competitors. (Bluesky membership was an invitation-only affair until recently.) The site has roughly 4 million users, compared to an estimated 130 million on Threads and, as of last September, 550 million on X/Twitter. 

Neither party commented on the reason for Dorsey’s departure from the board.

Jack Dorsey’s praise for X was just as noteworthy as his exit from Bluesky, however. He and Musk have had a relationship that has seemingly tilted from full-throated support to barely disguised disdain for the better part of the past two years.

To get a sense of how volatile the relationship has been, it helps to start four years ago, in the heart of the pandemic, when activist investor Elliott Management was looking to oust Dorsey from his position as CEO of Twitter. Elliott, at the time, had bought up 4% of the company’s stock to become Twitter’s biggest shareholder and did not like that Dorsey was focusing on both the social media site and his financial services company Square.

Musk was one of the first people to support Dorsey, tweeting, “Just want say that I support @Jack as Twitter CEO. He has a good ❤️.”

Dorsey echoed that support in 2022, when Musk announced he would join Twitter’s board (before ultimately deciding to purchase the company entirely instead). “I’m really happy Elon is joining the Twitter board! He cares deeply about our world and Twitter’s role in it,” Dorsey wrote. “Parag [Agrawal] and Elon both lead with their hearts, and they will be an incredible team.”

(Walter Isaacson’s 2023 biography of Musk suggested the leaders struck a private deal surrounding Musk’s purchase of Twitter as Dorsey began to get cold feet about selling the site.) 

Weeks later, when things had become hostile between Musk and Twitter’s board, Dorsey seemed to side with Musk, writing, “it’s consistently been the dysfunction of the company” in reply to a reader who pointed to “plots and coups” on the Twitter board.

In April of that year, he was as clear as could be, writing, “In principle, I don’t believe anyone should own or run Twitter. It wants to be a public good at a protocol level, not a company. Solving for the problem of it being a company however, Elon is the singular solution I trust. I trust his mission to extend the light of consciousness.”

Dorsey rolled over more than 18 million shares in Twitter into the new Musk-owned company as an equity investor, rather than receiving a cash payout, according to a filing with the Securities and Exchange Commission (SEC).

That trust lasted just one year, though. In the summer of 2023, Dorsey slammed Musk’s decisions at the social media company, which included layoffs and doing away with the verification system. "> Appearing on the Breaking Points YouTube channel, Dorsey criticized Musk’s handling of the site, saying the lawsuits surrounding the deal led to bad decisions.

“I think it set up a dynamic where he had to be very hasty, he had to be impatient, and he had to move as quickly as possible with features even if they weren’t fully thought out,” Dorsey said. “It all looked fairly reckless.”

Dorsey doubled down on these statements on Bluesky, saying Musk shouldn’t have gone through with the deal to buy Twitter.

“It’s pretty sad how it all went down,” wrote one user, to which Dorsey replied, “Yes.”

The X endorsement was part of a busy weekend for Dorsey on the platform. He also unfollowed almost all accounts, except for Musk, Edward Snowden, and Julian Assange’s wife and lawyer, Stella Assange. Musk, so far, has not publicly responded to any of Dorsey’s recent comments. 

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