as CEO, user growth had stalled, the stock
had declined nearly 70% since its high
following the IPO, the company was on
track to lose more than $500 million in
2015 alone, and a number of highly regarded employees were about to leave.
Although Twitter made some progress
in releasing new products, including
Moments and its live-video features, it
struggled to refresh its core experience.
In January 2016, Dorsey teased users with
an expansion of Twitter’s long-standing
140-character limit, but it took another 22
months to launch 280-character tweets.
“Twitter was a hot mess,” says Leslie Mi-
ley, who managed the engineering group
responsible for safety features until he
was laid off in late 2015. “When you
switch product VPs every year, it’s hard
to keep a strategy in place.”
Then the U.S. presidential election
arrived. All of Twitter’s warts were about
to be magnified on the world stage. Twit-
ter’s support agents, the ones reviewing
flagged content and wading through the
darkest muck of social media, witnessed
the earliest warning signs as Donald
Trump started sweeping the primaries.
“We saw this radical shift,” says one at
the time. Discrimination seemed more
flagrant, the propaganda and bots more
aggressive. Says another: “You’d remove
it and it’d come back within minutes,
supporting Nazis, hating Jews, [memes
featuring] ovens, and oh, the frog . . .
the green frog!” (That would be Pepe, a
crudely drawn cartoon that white su-
A July 2016 troll attack on SNL star Leslie Jones—incited by alt-right provocateur
Milo Yiannopoulos—proved to be a seminal moment for Twitter’s antiharassment
efforts. After Jones was bombarded with
racist and sexist tweets, Dorsey met with
her personally to apologize, and the company banned Yiannopoulos permanently.
It also enhanced its muting and blocking
features and introduced an opt-in tool
that allows users to filter out what Twitter
has determined to be “lower-quality content.” The idea was that Twitter wouldn’t
be suppressing free speech—it would
merely not be shoving unwanted tweets
into its users’ faces.
But these efforts weren’t enough to
shield users from the noxiousness of the
Clinton–Trump election cycle. During the
Jones attack, screenshots of fake, Photoshopped tweets purporting to show divisive things Jones had shared spread virally
across the platform. This type of disinformation gambit would become a hallmark
of the 2016 election and beyond, and Twitter did not appreciate the strength of this
new front in the information wars.
“You end up going down a slippery slope,” says a former
C-level Twitter executive when asked about why the service
can't fix some of its abuse woes. “;‘Oh, the simple solution is X!’
Lots of these easy solutions are a lot more complex.”