While Jack Dorsey Mans the Monastery 

The small but boisterous slice of Twitter that's preoccupied with politics imagines @jack, the author of our collective Twitter being, as all-powerful. He's not.
illustration of Jack Dorsey
Illustration: Sam Whitney

The day of January 6, when he hurled down the lightning bolt that cast Donald Trump out of Twitter and into outer darkness, should have been @jack's debut as an imperial overlord. But @jack never seems to flex. This can be maddening. Just when you want him to act Churchillian, @jack is more reticent than ever, a cipher, more Sphinx than Zeus. Last summer, The New York Times asked Jack Dorsey whether he's “one of the most powerful people on earth,” and his voice was like a dial tone: “No.”

On January 13, @jack threaded ambivalently about the Trump ban, ruminating on the question of how to address “offline harm as a result of online speech” while holding sacred “the noble purpose and ideals of the open internet.” He left his pensées unfinished.

Dorsey doesn't generally use Twitter to tweet. “I use it to listen and to observe and to understand our world and my world and myself,” he told the Times. At the same time, he views Twitter as a cosmic verity, a force that mysteriously predates his cocreation of it in 2006. Twitter “wasn't something we really invented. It was something we discovered.” Like suffering, like samsara, Twitter was just always there.

Forty-four-year-old Jack Patrick Dorsey, the reclusive and peripatetic maxibillionaire from St. Louis, exists, presumably, in time and space, somewhere behind his Twitter handle. But it's @jack, that numinous avatar, that's credited with bestowing on his kingdom the relative well-being, quiet, and order that appears to bless us only when Donald Trump is in exile from civilization. The nation would come to know these unfamiliar sensations at the inauguration of President Biden, weeks after @jack, or someone acting in his name, enacted the excommunication. In retrospect, @jack was not just decisive and swift; he was prescient. So he could be forgiven for giving a spike-the-football press conference. But in the weeks since, he's remained every bit as elusive as Q. Or the Holy Ghost. Or Shiva the Destroyer.

And so it has been, for four strange years. @jack is everywhere and nowhere. He's either the emperor of geopolitics or a lost druid. The relatively small but boisterous slice of Twitter that's preoccupied with American politics has come to imagine @jack, the author of our collective Twitter being, as all-powerful. We call out for him, but he stays silent. We beg him to smite trolls; he does nothing. We plead for him to exile Nazis; he retreats to a meditation cushion. Sometimes (as in 2017) he adds characters to our rations. Sometimes (as in 2020) he introduces Fleets, which no one asked for. Because, like other deities, he's capricious—and often seems not to exist—we're stuck with tea leaves: what he likes, tweets, retweets. None of it adds up. All that can be said with any confidence is that @jack in general likes a laissez-faire Twitter—whether out of Buddhist acceptance of what is, blithe indifference, catch-all libertarianism, or anxiety about his untrained capacity for moral discernment.

When incarnate, as in occasional appearances and paparazzi photos, Jack Dorsey does little to give the lie to the online fantasy of him. In October, as he testified before Congress via video, he wore a foot-long gray-brown beard and a gold ring in his left nostril. Once a Missouri fashion model and tinkerer enchanted by dispatch technology, then a springy boyish billionaire on the TED-Davos circuit, Dorsey has now gone full Elminster Aumar. His deep-set eyes can still be called piercing, and the vanity of his early blue-steel pose is not lost. What is lost is the look of complaisance that defines young founders looking for capital. Dorsey, like @jack, no longer truckles to anyone.

But there's a twist. There is one at Twitter who takes action while Dorsey mans the monastery. She is Vijaya Gadde, Twitter's former general counsel, and now head of legal, policy, and trust and safety issues. At 46, Gadde wields so much influence at Twitter that she terrified the gnarly crowd at the late wingnut social platform Parler. One Parlerite called her “Goebbels in a pantsuit.” Another warned, “You don't know her face or name because she rules in the shadows.”

Off the mark, of course. Unlike Dorsey, Gadde is famously non-shadowy and forthright. Born in India, she grew up in Southeast Texas when it was still studded with sundown towns, which shut out people of color with threats, violence, and racist statutes. When her father, a jobless chemical engineer, found work knocking on doors to collect insurance premiums, he had to seek permission from no less than the local Ku Klux Klan leader to walk in his own neighborhood. “My family felt very powerless in those moments,” Gadde said in 2016, when she was honored at NYU School of Law, from which she graduated in 2000. “When people ask me why I went to law school—I went to law school to make sure that people have a voice and that people have someone to fight for them.” She now sits on the board of Mercy Corps, a global humanitarian group and NGO that is currently working to provide emergency supplies to especially vulnerable families and communities during the Covid-19 crisis.

Gadde's earnest moral commitments at Twitter might be explained in part by timing. She joined Twitter not at its start as a group-text goof by Dorsey and his crew in 2006, but in 2011, one decade ago, when it moved to center stage as a communication nexus for the so-called Arab Spring. Where most current social media leaders had no idea what they were getting into in the lighter-hearted days of Web 2.0, Gadde instantly saw the seriousness of the endeavor. She could see Twitter's activist possibilities, as well as its exploitation by those looking to stoke disinformation and racist speech. Above all, as she rose in the ranks, she gained Dorsey's druid ear. As one Twitter official told Politico, “I can't imagine a world where Jack looks at [Gadde] and says, ‘No.’”

In fairness, digging in and impeding change is not Dorsey's thing, so Twitter may for the foreseeable future be synced to the clear-eyed moral vision of Gadde, whose Twitter feed, @vijaya, is focused more on Amanda Gorman's poetry and public health infrastructure than on Bitcoin, a topic that preoccupies @jack.

And while Gadde tweets without reservation about human rights initiatives and progressive projects she admires, and brooks right-wing trolls, the CEO of Twitter continues to be singularly ill-suited to the world of barbs and quips he helped create. He openly prefers the otherworldly interconnectiveness of the service to the tweets that serve as its component parts. When Dorsey reflects on the dynamic of tweeting in interviews, he still hearkens back to the heady early days, when it was “amazing” to be able to tell friends all at once, by making phoness buzz in their pockets, that you were headed to a yoga class.

When he had to show up to thread about the Trump ban on January 13, though, he showed up as himself. He expressed his uncertainty, spoke with little ego, and made it clear he was just another human, improvising on insufficient data, hoping to promote both peace and openness in a world where those values are sometimes at odds. However much Twitter might urge him to play oracle, @jack will refuse. The last sentence of the thread's intro tweet would make an excellent epitaph and an excellent koan: “Was this correct?”

This article appears in the March issue. Subscribe now.

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