Now there are increasingly frequent indications that he has broken with Musk and the bull-in-a-china-shop management style the Tesla boss has adopted since his $44 billion October acquisition of the microblogging platform, which Dorsey cofounded in 2006.

Posting on Nostr on Wednesday, the fintech boss criticized the latest snafu under Musk that limited the number of tweets users could post: “Twitter went from real time to 1 minute delay,” he wrote. 

The needling, while reserved, is a far cry from his previous full-throated support and seems symptomatic of an estranged relationship between the two once-close tech figures. 

Dorsey has found himself forced to watch from the sidelines as Musk repeatedly bad-mouths his most famous creation, notably through the so-called Twitter Files. These attempt to document a political bias inherent in Twitter that shadowbanned conservative voices, a key issue Musk initially sought to address when he approached the company in April.

There have also been veiled personal digs from Musk. In one example, Musk’s attempt to protect Dorsey from the ensuing right-wing outrage read more like a damning critique of the latter’s management style, painting him as a well-meaning but ultimately clueless and inept leader out of his depth. “The inmates were running the asylum,” Musk wrote. “Jack has a pure heart.” 

Dorsey has also taken issue with Musk’s characterization of Twitter as a safe space for child pornography traffickers. “It is a crime that they refused to take action on child exploitation for years!” the new Twitter owner posted in early December in a reply to Mike Cernovich.

The alt-right influencer had demanded prison for the three members of Twitter’s Trust and Safety Council, who had just resigned publicly in protest over Musk’s mismanagement, for failing to remove child pornography.

Musk was once the only one Dorsey trusted to act as Twitter steward

“To say we didn’t take action for years isn’t true,” Dorsey told Musk. “You can make all my emails public to verify. Company took away my access to email or I would.” (Musk stood by his claims that he was the first to make child safety an immediate top priority, while Twitter execs like finance chief Ned Segal were more interested in snagging expensive seats at basketball games.)

The Twitter cofounder was the last person one might expect would fall out with Musk. 

Court records show he lobbied internally for Musk, easily among the most adept content creators on the platform, to join the company’s board when it was under attack by Paul Singer’s activist hedge fund Elliott Management. 

When Musk shocked Twitter management by announcing he owned nearly a tenth of the company last April, it was Dorsey who vouched for the Tesla CEO at a subsequent board meeting. His credibility as cofounder helped garner an invitation for the centibillionaire to join as a director.

After the mercurial entrepreneur then changed his mind, Dorsey was there to support Musk’s unsolicited takeover bid for the company, prompting calls that Dorsey was a turncoat who’d stabbed the board in the back. 

“Elon is the singular solution I trust,” Dorsey wrote in late April. “I trust his mission to extend the light of consciousness.”

It appears as if that trust has run out.