36 new york | september 16–29, 2019
Broadly speaking, Silicon Valley remains
socially liberal and anti-Trump. Its boards
and executive floors are stacked with
Obama-administration alums. But what
once seemed like an intuitive mutual
understanding between the emerging
Democratic majority and the robber bar-
ons of the 21st century has grown into
something more mutually suspicious,
sometimes even hostile. Technologists no
longer unquestioningly assume the more
liberal party actually shares their values,
and Washington Democrats are no longer
willing to be seen by tech billionaires as
know-nothing functionaries who can be
counted on to do their bidding. In 2017,
when a nationwide listening tour
prompted widespread speculation that he
was running for president, Mark Zucker-
berg was asked about his political plans at
another company Q&A. No offense to the
presidency, he said, but I already run a
community of 2 billion people.
Today, tech leaders are baffled and
angry that Democrats so routinely
question their motives. Who do
they think they are?
And while it took the 2008
financial crisis—and the decade of
fallout that followed—to tear Dem-
ocrats from Wall Street, the onset of
their breakup with Silicon Valley
happened much more abruptly.
This decoupling reflects the
tarnished reputations of once-
gleaming companies like Face-
book, Google, and Amazon, still
widely trusted but increasingly
damaged, especially on the left,
by public furor over election
interference, monopolistic prac-
tices, and labor policies. It
reflects, too, a more populist Democratic
Party, which sees tech monopolies not as
the swaggering future of corporate Amer-
ica but as a target for a revived antitrust
movement. (“The fact that within the first
five minutes of the first debate of the
entire season, antitrust came up—how far
are we from 2008?” asks Facebook co-
founder and Obama 2008 “online orga-
nizing guru” Chris Hughes, who in May
called for the company’s dismantling and
labeled his Harvard roommate Zucker-
berg’s power “unprecedented and
un-American.”)
Partly it reflects the rise of the alt-right
and increasingly open libertarian sympa-
thies among leaders in Silicon Valley,
along with the growing divide between
some of those bosses and the rank and
file, who are much less comfortable with
Trump. (Elizabeth Warren was the big-
gest recipient of Google-employee cam-
paign donations over the first half of
2019, even as she threatened to separate
the company’s central businesses.)
But this isn’t just an ideological story or
an inevitable one. Some blame for the
breakup lies with the calculated maneuvers
of just a few politicians on the rise and the
blunders of a few big-money techies look-
ing to play politics, with neither party will-
ing to pay the deference the other felt was
required. Democrats might’ve been a lot
more willing to forgive the sins of Big Tech
if its executives had performed even the
smallest show of political humility or con-
trition in their responses to political scan-
dals or in their outreach to candidates.
Or if some hadn’t been so shameless in
their courting of Trump or their ham-fisted
playacting of distance from Democrats in
response to Republican accusations of
bias—one leading industry group pre-
sented its Internet Freedom Award to
Ivanka Trump in May, for instance. Com-
plaining about tech leaders, the
chair of one state Democratic
Party told me that at this point,
“the only way for them to redeem
themselves is to write big checks,
which they’re not doing.”F THE QUESTION about banks
befuddled Zuckerberg at the town
hall, it would’ve made sense to
Warren, who, in private meetings
on Capitol Hill as early as mid-
2017, was explicitly comparing the
country’s tech leviathans to the
pre-regulation giants of high fi-
nance because of their informa-
tion advantages over consumers
and their D.C. influence. Over the
next two years, she effectively
made it politically impossible for her seri-
ous rivals to offer Silicon Valley outright
praise. break up big tech read a billboard
her campaign put up outside San Fran-
cisco’s main Caltrain station this spring.
Last September, Bernie Sanders re-
branded legislation from Bay Area con-
gressman Ro Khanna as the “Stop Bad
Employers by Zeroing Out Subsidies Act”
(Stopbezos), aiming to pressure Amazon
into increasing workers’ wages. Sensing
trouble, Amazon calculated it would be
worth back-channeling with Sanders’s
staff and invited the Vermont senator on a
warehouse tour even as he ratcheted up
public pressure. Sanders pushed on, and
in October Amazon announced a $15
minimum wage for its U.S. workers. Sand-
ers got no heads-up, but the left felt
empowered. The company was reluctant
to play nice again if it meant another pub-
lic capitulation. The next month, when
Amazon announced its deal to place a sec-ond headquarters in Long Island City, it
did no concerted outreach to progressive
activists, figuring it already had sufficient
support from New York’s Democratic
mayor and governor, the latter having jok-
ingly offered to change his name to “Ama-
zon Cuomo.” As opposition to the deal
soon mounted, both Cuomo and Mayor
Bill de Blasio failed to get Bezos on the
phone, instead only occasionally connect-
ing with Jay Carney, the former Obama
White House press secretary now running
Amazon’s comms and policy arms. Ama-
zon had enough of the leftward pressure
and pulled out in February.
“Amazon came, Amazon left,” Warren
crowed a few weeks later in Long Island
City, announcing a new plan to “break up”
the biggest tech firms (which would actu-
ally have regulators undo a series of tech
mergers). “You know, that is the problem
in America today—we have these giant
tech companies that think they rule the
Earth. They think they can come to towns,
cities, and states and bully everyone into
doing what they want.”
Not everyone in the party saw it like
that. Among the 2020 candidates, none
have tried having it both ways on tech
more than Pete Buttigieg, the contender
who could fit most seamlessly into Sand
Hill Road tomorrow if he wanted to. But-
tigieg was Facebook’s 287th user as an
undergrad, knew Zuckerberg at Harvard,
and hosted him in South Bend in 2017. He
has criticized Google and appeared with
striking Uber and Lyft drivers, but he has
also raised money from or staged fund-
raisers hosted by Netflix chief Reed Hast-
ings; former Facebook exec Chris Cox;
Uber’s Chelsea Kohler; Google’s Scott
Kohler, John Flippen, Jacob Helberg, and
Clay Bavor; Nest’s Matt Rogers; Quora’s
Charlie Cheever; and Groupon’s Andrew
Mason. Buttigieg also tapped a Square
and Kleiner Perkins alum, Swati Mylavar-
apu, to run his finance operation and a
former Google big shot, Sonal Shah, to
lead his policy shop.
But even Buttigieg’s growing Silicon
Valley financial network pales in compari-
son to the operations assembled for can-
didates in recent election cycles after the
door between Big Tech and campaigns
burst wide open with Obama in 2008 and
the industry cemented its role alongside
Hollywood and Wall Street as one of the
party’s biggest backers. One reason for
this is that the field of candidates is so big
that investors are still hedging their bets,
giving to Joe Biden, Kamala Harris, Cory
Booker, and others. Yet none of the candi-
dates has publicly visited any of the tech
behemoths in person, unlike in previous
election cycles, when a Google stop was