It seems like the friendship between Elon Musk and Twitter founder Jack Dorsey is now all but over.

This week, Musk’s X Corp announced that it’s funding a lawsuit filed by a former employee of Block (former Square), the digital payments company owned by Dorsey, over comments made by said employee on X.

The employee, Chloe Happe, had shared various controversial opinions via her posts on X, across two separate X accounts.

Block dismissed Happe in November last year due to violation of its company policy, though Happe’s defense team claims that there are no provisions within Block’s employee regulations relating to external, non-business communications.

As part of Musk’s offer to fund the defense of anybody sacked because of their posts on X, X corp is now taking on the case, which will also put Musk at odds with Dorsey directly, and seemingly ending any chance of the two rekindling their mutual admiration and respect.  

Back in 2022, when the first reports circulated that Elon was looking to purchase Twitter, Dorsey was initially all in favor, even calling Musk “the singular solution that I trust” to rescue the app. Dorsey had previously put his support behind Elon joining the Twitter board, while the two had also shared various mutual interests, based on Twitter and cryptocurrency.

But post-acquisition, the respect and adoration between the two quickly soured.

It began with Elon’s “Twitter Files” expose, in which he sought to demonstrate how previous Twitter management had coordinated with government officials to censor speech. Musk initially tried to keep Dorsey out of the firing line, by publicly noting that these were not Dorsey’s decisions. But pretty soon, Musk was slating the entire company, Dorsey included, for what he perceived as restriction of free speech in the app.

Musk then further eroded his relationship with Dorsey by blocking links to competing apps, including Nostr, a decentralized social platform that Dorsey has long supported. Dorsey has also been critical of Musk’s moves to block links to Substack, again under the guide of anti-competitive behavior.

When asked about Musk’s takeover last year, Dorsey had changed his tone, saying that Musk had taken the wrong approach at the app.

This latest move looks set to further distance Dorsey and Musk, with Elon essentially taking aim at Dorsey’s own business. And while publicly, Elon will proclaim that this is nothing personal, he’s well aware of what’s he’s doing in this respect.

The real question, however, is whether this is a violation of free speech, as X contends, or whether Block was within its rights to fire Happe because of her comments.

Definitely, given its close links to social media, you can imagine that the Block team would be very aware of Happe’s Twitter/X personas, and you can only imagine that comments like the above example relate to specific employees at the company. That seems like a harmful mix, when employees are being made aware of Happe’s opinions on sensitive matters in a public forum.

But is that a fireable offense? We’ll find out, as X Corp takes Block to court.