June 7, 2023 - 1:00pm

In late January 2023, Jack Dorsey retweeted a classic: setting up my twttr”. His first tweet, from 2006, and the first ever message on the entire Twitter platform. It can now be read as a sign. After many years of maintaining a diplomatic silence, finally, Dorsey speaks.

The Twitter founder has always been the most airless of techs big dogs. Even Mark Zuckerberg has a kind of character to him, as crystallised in The Social Network: the nerd wrath, the Harvard smarm. But now, after years of punching way below his social importance, Dorsey would like to rebrand as a man with opinions. 

And an interesting set of opinions they seem to be. This week, he endorsed the presidential bid of Robert F. Kennedy Jr, the dynasty’s latest great hope. Junior has been picking up a surprising amount of support among the Democratic Party base, and Dorsey is now actively campaigning on social media for an open primary that could include him.   

Dorsey’s politics, however, are not so easily pinned down. As recently as 2020, for instance, he was giving $10 million to an Ibram X. Kendi-aligned “anti-racism” charity and marching down the streets of Ferguson, Missouri over police brutality. In 2013, he expressed his admiration for the law and order Democrat New York City mayor Mike Bloomberg. Later, he gave small sums to the two renegade candidates in the Democratic primaries: the anti-woke anti-interventionist Tulsi Gabbard, and the innovative libertarian Andrew Yang.                  

Back when he was running Twitter, Dorsey would get it in the neck from both sides, and it clearly weighed heavily on him. All the while, he appears to have been mulling potential solutions. There is now good evidence that he was a strong supporter, if only behind the scenes, of Elon Musks Twitter takeover.

A new platform is needed. It cant be a company. This is why I left,” Dorsey texted Musk, according to a cache of messages that emerged during the latter’s court case over his intended purchase of Twitter.

Dorsey buys into what may well be Musk’s long-term vision, too. Namely, that “censorship” should never exist — that the problem of top-down imposition of value judgements can be done away with by creating networks that can be fitted around individual user preferences (hence the creation of his latest project, Bluesky).

The best, most charitable interpretation of Dorsey might be that he’s quintessentially Generation X. Which, at 46, he is. He dreams of a ’90s alternative world: of the vision of a Left that existed at the time of the Seattle Riots, embodied by Noam Chomsky, or Naomi Klein’s once essential book No Logo. At once suspicious of corporate power and government power; anti-war, committed to social justice, but not to Social Justice. It certainly goes some way to explaining his staunch defence of Edward Snowden.

Just as with Bluesky, Dorsey has used his payments company Block to explore a new kind of world wide web driven by micro-payments through Bitcoin and other cryptocurrencies. While others are fixated on AI singularities, Dorsey seems to be trying to build a kind of “full stack” of products that put the ordinary citizen beyond the power of government overreach. 

So if Dorsey has a political philosophy, it is that the powers that be should not be trusted.” Yet he is quite obviously one of the key powers of our age. That’s the strangeness of him. And one of the reasons it’s worth trying to understand him.

Gavin Haynes is a journalist and former editor-at-large at Vice.