Twitter chief executive officer Jack Dorsey looks on during a Senate Intelligence Committee on September 5, 2018 in Washington, D.C. (Drew Angerer/Getty Images)

Twitter Is About to Get Way Worse

Defending free speech in a time of ascendent authoritarianism was always a losing battle. But Jack Dorsey tried.

I am a Twitter addict. It’s true of most journalists, and it’s true of me. But although I’ve given the platform more hours than I’d ever like to know, I have no idea how Twitter the company really works.

So, when Jack Dorsey, the co-founder and CEO of Twitter, and the company’s bearded public persona, announced this week he was stepping down, I wanted to know something basic: was this, on balance, good or bad? Especially when it comes to the value I think is so vulnerable: freedom of speech. 

How would it affect the ongoing fight between those advocating for chaotic, open conversations online and those who embrace censorship and advocate for top-down control? I fall on one side of this more often than not, but it’s not always simple. 

I reached out to Mike Solana, one of the most insightful (and irreverent) voices in tech right now, to explain what Dorsey’s resignation means.

Mike is a vice president at Founders Fund—Peter Thiel’s venture capital firm, which has invested in transformative brands like AirBnB, Stripe, and Lyft—and he writes one of the sharpest, punchiest, funniest Substacks in all the metaverse: Pirate Wires. — BW

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For anyone who cares about free speech, Jack Dorsey was the villain. But I wonder if this was mostly a matter of aesthetics. Let’s be honest, the guy just always kind of looked like someone who wanted to censor you.

It was that “#staywoke” shirt he used to run around in, I think. It was the nose ring, probably. Then, I guess it also could have been the last five years of partisan Twitter policy culminating in the deplatforming of a sitting president—I mean honestly who knows. But my sense is, despite appearances, Jack is actually at odds with his company’s drift into authoritarianism, and he’s been quietly protecting many of the values he’s often attacked for debasing. 

Alas, Monday, he stepped down as CEO of Twitter. Today, what’s left of our open internet is already less safe. 

In looking ahead for some sign of what’s to come, I think it’s first important we look back at what Twitter did to the New York Post. In October 2020, the paper published a story on Hunter Biden’s laptop that strongly implied Joe Biden, then the presidential nominee, was corrupt. The story was immediately shut down by Facebook, which reduced traffic on the offending piece pending a third-party review (that seems not to have happened). But Twitter blocked the piece entirely, and then took the additional steps of locking the Post out of its account and prohibiting every user in the country from sharing a link to the offending piece over private messenger. 

This extraordinary act of censorship—an overtly political censorship of private communication just before a presidential election—made global news, and would have been alarming even if the Post’s story turned out to be untrue. (It has not). 

But at the time, for me at least, Twitter’s censorship wasn’t so shocking as its CEO’s reaction: 

Jack was mortified and angry. We saw for the first time strong evidence of a social machinery beneath him at Twitter with which he was clearly in conflict: he went on to criticize his company’s handling of the Post debacle repeatedly, and then before Congress, which is really when he told us who he was.  

Following our incredible election season of censorship, which infuriated the right, and the Capitol riot on January 6, which infuriated the left, several tech executives were called before Congress to testify on a disinformation panel. It was a complete and glorious shitshow. But it wasn’t all miserable. Jack brought a glimmer of old internet culture. He not only regretted previous instances of Twitter censorship, but insisted he’d implemented changes to prevent something so draconian as the Post censorship from occurring again. Then, when pressed on theoretical federal censorship, he expressed forceful, almost disrespectful, opposition to the concept. 

This was no savvy political answer, delicately minding the bloated egos of men and women capable of destroying his company. Jack Dorsey appeared before Congress looking like a haggard, bearded sage from the future, fallen back in time from some dystopian hellscape to save us from ourselves. Not only did he not trust Congress with the power of censorship, he didn’t trust himself. In fact, he argued, it was a power that should literally not exist. Finally, he declared under oath he was presently attempting to make sure censorship of the sort being considered by Congress could, in fact, never be considered again. 

Under Jack’s direction, Twitter has been working on a decentralized social media protocol called Bluesky. In other words, by leveraging blockchain, his intention is to build a platform with no boss. The project is still in its research phase, and there’s a lot about it we don’t know, but it seems the protocol would in practice naturally build a kind of censor-proof social media backbone on top of which applications like Twitter would sit. In this way, Twitter might be reduced to a single lens through which you engage with the social internet. It would no longer be the social internet. Twitter could revoke its single lens from you, for failing to follow some ridiculous new speech code, for example. But in a world of Bluesky you couldn’t be erased for the infraction. 

Jack is also a man who, it must be said, truly refuses to shut up about Bitcoin, a decentralized digital currency. These are anti-authoritarian tools. He hasn’t pursued them because he doesn’t understand them. He’s pursued them because he’s been resisting the authoritarian impulses of the people around him, as well as the media and government, for years. He’s pursued them because he believes the world needs them. 

Thank you, in other words, is I guess what I’m getting at. 

Twitter, the purest distillation of our social internet, changed the way we think and opened us to all manner of new concerning social possibilities. But it also hugely contributed to the destruction of our pre-existing hegemonic media Death Star. Cultural outcasts often complain about censorship on the app, but the legacy of Twitter under Dorsey is far more a legacy of empowering heretical voices—voices that could not have existed in a socially meaningful way even 20 years ago—than it is a legacy of silence. (Let’s be real: I am writing this piece for a newsletter founded by a former New York Times editor who, in a pre-Twitter universe, would have been shoved out of The Times and never heard from again.) 

Twitter liberated information. It empowered the counter-voice. Then, most importantly, it gave our stagnant cultural overseers an outlet to simply tell us, honestly, who they are and what they believe, which was, of course, sufficiently horrifying to free us all from the notion they should retain their position of cultural dominance. 

In 2016, when Jack wore that much discussed #staywoke shirt to an otherwise beside-the-point tech conference, it was read as an overtly political statement. And it was political. But not in the way it was interpreted on the political left, as too little moderation too late, or the political right, as a commitment to censoring wrongthink. When pressed, Jack explained exactly what “woke” meant to him, explicitly in terms of the institutional media, which he implied had been lying to us. His answer, insufficiently partisan, characteristically succeeded only in infuriating everyone, which is why he was, in my opinion, the best man for a job that no man should have. 

According to Jack, staying “woke” meant looking at the world with your own eyes, sharing what you saw, and judging it for yourself. His promise was to empower average people to do these things. Yes, he’s made mistakes along the way. But he delivered on his promise, and it is on this delivered promise his tenure should be judged. Still, against the committed efforts of leaders in media and politics, as well as many of his own employees, defending freedom of expression in a time of ascendent authoritarianism was always a losing battle, or at least along the dimensions of Web 2.0. 

It’s been 24 hours since Jack’s resignation, and while I’m not really interested in the evolving loser drama surrounding the new CEO’s decade-old tweets, it is worth noting that Twitter has already updated its content policy in a manner that effectively makes citizen journalism impossible. Things will only get worse. There is perhaps more Jack could have done before he left, but I think we’re all about to realize just how much he was doing, quietly, in stewardship over a power he was wise enough to fear, and good enough not to use. 

Godspeed, bird king. You’ll be missed. 


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