Dorsey, Musk, Trump and the battle for Twitter
IN August 2016, Twitter secured a $5mn advertising deal with Donald Trump’s election campaign, including the promise that it could have an emoji automatically run alongside a bespoke hashtag. Most brands use an image of their logo, but the campaign wanted to employ the emoji of a robber running away with a bag of money. The hashtag? #CrookedHillary.
Days before it was supposed to go live, Twitter balked. Trump’s team was furious, and pulled part of the deal. “For [then chief executive Jack] Dorsey and Twitter, it was an embarrassing and costly introduction to dealing with Trump,” writes Bloomberg journalist Kurt Wagner in his new book Battle for the Bird. “It was also a reminder of the power it suddenly had.”
Dorsey’s anxiety about this power — and the question of what happens when Elon Musk wields it — lies at the heart of Wagner’s book. He draws on dozens of interviews, leaked documents, court filings and public statements to chronicle the Dorsey era, which now seems like a distant memory, as well as Musk’s dramatic first year at the helm.
Another book, Extremely Hardcore by Zoë Schiffer, is a sharp and deeply sourced fly-on-the-wall account of similar subject matter — focusing in particular on the impact of the takeover on Twitter’s staff, thousands of whom had their lives upended by Musk’s job cuts and overhaul of company culture when he took control of the business in October 2022 and renamed it X.
“It’s a business case study, a labour investigation, and a murder mystery,” explains Schiffer, a journalist at Platformer, an online tech publication. “The body count is still being tallied”. It’s also packed with original reporting; Schiffer single-handedly broke a great deal of news on Twitter’s inner workings herself.
Dorsey and Musk represent the extremes of leadership. Dorsey’s hands-off style led Twitter to breaking point, the authors argue, only for Musk’s hardcore approach to break it some more. While much ink has been spilled on Twitter as the saga has unfolded, these titles are an important exploration of the impact of personality and politics on communication tools so powerful and ubiquitous that some argue they should be public utilities.
But first: Dorsey. After co-founding Twitter in 2006, he was chief executive until he was fired in 2008, only to return to that position again in 2015. From the outset, he loathed the perennial challenge of maintaining a “healthy” space while also enabling free speech.
In Wagner’s telling (Dorsey himself declined to be interviewed), between 2015 and 2021 the eccentric, intermittent-fasting, ice-bathing CEO fashioned a rambunctious but collaborative company culture, hosting gaudy work events (at one, the chief financial officer “wore glow sticks around his neck and bright orange suspenders”) and delegating much decision-making.
Over time, however, Dorsey — born to a Republican father and Democrat mother and “a huge proponent of transparency” — grew uncomfortable with moderation decisions made by his subordinates. These decisions included cutting down on Covid misinformation, suppressing the New York Post’s 2020 exposé on Hunter Biden’s laptop, and eventually banning Trump in the wake of the January 6 2021 riots at the US Capitol.
Instead of stepping in, Dorsey checked out, part bruised by attempts by aggressive activist investor Elliott Management to oust him, part distracted by his bitcoin endeavours. He seems to have believed that the man to rescue Twitter was Musk, for whom he has a sycophantic adoration, and was instrumental in supporting his $44bn approach.
As has been widely reported, Dorsey’s faith in Musk turned out to be grossly misplaced. With a mega-rich provocateur in charge, and no board of directors, “the power that Dorsey so worried about has only been further centralised”, Wagner writes.
What emerges in both books is a gaping chasm between Musk’s selfdeclared devotion to free speech — fighting what he has repeatedly called the “woke mind virus” — and the day-to-day use of his power as leader, which often seems capricious. Neither book explores the enthusiasm of some prominent figures in the tech industry for free speech. Schiffer suggests that the hardening of Musk’s libertarian views (he has previously voted Democrat) may be personal; he believes “woke” culture affected his trans daughter, who has now disavowed him and become a Marxist.
Perhaps the greatest example of Musk’s libertarianism coming up against his own ego occurred in February 2023, when US President Joe Biden got more views than the billionaire on a tweet about the American football Super Bowl. According to Schiffer, the Twitter CEO’s response was to order an “all hands on deck effort” from engineers to determine why, and artificially boost his own tweets.
In the past 15 months, as the platform has become increasingly rowdy, advertisers have pulled away, edging the company close to bankruptcy. Just like Dorsey before him, “Musk seems to be learning the hard way that having power and control over global speech is a much greater burden than most people realise,” Wagner writes.
Notably absent from both accounts are insights from those left holding the bag. What of the Wall Street bankers — Morgan Stanley, Bank of America, Barclays — who loaned Musk $13bn for the purchase? Or the equity investors, such as Larry Ellison, billionaire founder of Oracle, who put in $1bn? Do they care about his chaotic business decisions thus far? Or do they have faith in his ability to turn things around in the longer term?
There are rare flashes of success. In 2023, Twitter embarked on a savage cost-cutting exercise directed by Musk’s inner circle, saving $1bn — double their $500mn goal, according to Schiffer. But always there seem to be unintended consequences: it remains unclear if Twitter will face lawsuits for refusing to pay bills or regulatory action, as the Federal Trade Commission hovers.
Presumably because of their publishing schedules, both books stop in 2023, but this story by no means finished. So far, Musk appears to be a man without a plan. As we head into a year of dozens of elections globally, and increased fears about the spread of misinformation, it seems likely that he will keep us guessing.