Of the two presidential campaigns, Trump’s better knew how to take advantage of the service to amplify
its candidate’s voice. When Twitter landed massive ad deals from the Republican nominee, left-leaning
employees complained to the sales team that it should stop accepting Trump’s “bullshit money.”
The ongoing, unresolved disputes over what Twitter should allow on its platform continued to flare
into the fall. In October, the company reneged on a $5 million deal with the Trump
campaign for a custom #CrookedHillary emoji. “There was vicious [internal] de-
bate and back-channeling to Jack,” says a source involved. “Jack was conflicted.
At the eleventh hour, he pulled the plug.” Trump allies later blasted Twitter for
its perceived political bias.
On November 8, employees were shocked as the election returns poured in,
and the morning after Trump’s victory, Twitter’s headquarters were a ghost town.
Employees had finally begun to take stock of the role their platform had played
not only in Trump’s rise but in the polarization and radicalization of discourse.
“We all had this ‘holy shit’ moment,” says a product team leader at the time,
adding that everyone was asking the same question: “Did we create this monster?”
In the months following Trump’s win, employees widely expected Dorsey to
address Twitter’s role in the election head-on, but about a dozen sources indicate that the CEO remained
mostly silent on the matter internally. “You can’t take credit for the Arab Spring without taking responsibility for Donald Trump,” says Leslie Miley, the former safety manager.
Over time, though, Dorsey’s thinking evolved, and he seems to be less ambivalent about what he’ll
allow on the platform. Sources cite Trump’s controversial immigration ban and continued alt-right manipulation as influences. At the same time, Twitter began to draw greater scrutiny from the public, and
the U.S. Congress, for its role in spreading disinformation.
Dorsey empowered engineering leaders Ed Ho and David Gasca to go after Twitter’s problems full bore,
and in February 2017, the company rolled out more aggressive measures to permanently bar bad actors
on the platform and better filter out potentially abusive or low-quality content. “Jack became a little bit
obsessed,” says a source. “Engineering
in every department was asked to stop
working on whatever they were doing
and focus on safety.”
Twitter’s safety operations, previously
2017, for example, after learning how
as a combination of product and policy.”