24 new york | march 2–15, 2020
“We presented Mike with data, which I actually did move up a few
days because I did recognize what the calendar was,” says Sheekey.
If Bloomberg decided to run, even skipping all the primaries before
Super Tuesday, his team still needed to file petitions for his candi-
dacy in Alabama right away. “We met with Mike about three days
before that deadline, with no real urgency that that was a serious
concern—but it was material.”
The next morning at seven on the dot, Sheekey’s phone went beep-
beep-beep. “He goes, ‘Hey, it’s Bloomberg.’ I said, ‘Yep.’ He goes, ‘Okay,
so I guess we’re going to do this thing.’ Fortunately I was sitting at
the time.” Sheekey got on the horn with an advance man in Arkan-
sas, “which struck me as reasonably close to the state of Alabama.”
Sheekey told him, “ ‘I need you to get every single person you know
into Birmingham by this afternoon.’ He said to me, ‘Does this mean
what I think it means?’ I said, ‘It sure does.’ All I heard was, ‘Yahoo!’ ”
As a candidate, Bloomberg sells himself as a management savant
who can fix the federal government. Maybe there was a constitu-
ency for him: Supporter and congressman Ted Deutch of Boca
Raton says, “The kind of people I grew up with in Pennsylvania, my
neighbors in Ohio, and now in Florida—these folks in swing states
who turned up in 2018 to send a message to President Trump—just
want a president that lets the country function again.” He certainly
built an extraordinary election machine almost out of thin air.
Within six weeks, Bloomberg had hired nearly a thousand employ-
ees and transformed an empty floor of a neo-Gothic building near
Times Square that once housed the New York Times (and is now
partially owned by the Kushner family) into his headquarters.
Up in the waiting room, an ad plays on a flat-screen TV about
low-income and minority pregnant women and how they die more
than white women (but Mike will fix that). Two countdown clocks
hang above the TV, one marking the days until Super Tuesday and
the other the days until the national election. The folks here don’t
seem like run-of-the-mill campaign volunteers; they’re middle-
aged political mercenaries in fleece with time-tested strategies and
robust Rolodexes. A political consultant tells me, “They’ve hired the
whole goddamn world and have a lot of credible people. It’s not like
Trump’s first campaign, with people working for him you’d never
heard of before—which, by the way, definitely worked.” Bloomberg
has recruited from his City Hall and hoovered up people from shut-
tered presidential campaigns (Kamala Harris, Andrew Yang).
He’s always treated employees to salaries, health care, and
bonuses beyond industry standards and is now paying many mul-
tiples more than other campaigns, plus free furnished apartments
in Manhattan. “This is the kind of campaign we’ll never be on
again in our lives!,” exclaims one staffer, incredulous at his new
Bloomberg-issued iPhone 11, the free booze, and the three catered
meals a day (peeking in the campaign café at dinnertime, I spied
pizza and tuna steak). Even the lowest-level campaign workers, like
a yoga teacher who says they’re making $6,000 a month just to
canvass for him—work that almost every other campaign relies on
volunteers for—share some of these benefits.
“As my uncle says, ‘Rich or poor, it’s nice to have money,’ ” says
senior adviser Howard Wolfson, an architect of Hillary ’08 and a
longtime Bloomberger, usually wearing AirPods in his ears and a
Cheshire-cat grin. “Would you pay for people’s Ubers” to get them
to the polls?, I ask him. “Sounds like a good idea,” he says, and it’s
not entirely clear he’s joking. But you can’t make people vote for
you, he says. “I’ll take the Uber and vote for someone else.”
To anyone on the outside, it looked like Bloomberg was trying to
buy the nomination, and indeed, he was. People at Bloomberg
Philanthropies who’d distributed many of his millions to American
cities were the same folks facilitating asks to the same mayors and
other legislators about endorsing Bloomberg. And even only half-
informed voters could see that it was probably impossible for
Bloomberg to win the nomination outright and intuited, therefore,
that the mayor’s plan was to drive Democrats to generational infight-
ing at a contested convention in Milwaukee in July, which struck fear
in their hearts: If they didn’t unite behind someone until July, the
party stood a good chance of losing again to Trump.
Bloomberg must’ve known Democrats would figure this out
eventually, and when they did, they’d be pissed—so, partially as a
defensive maneuver, he made it clear he was only in this game to
defeat Trump, and even if he didn’t secure the nomination, he’d
keep up his payroll and also rain millions upon millions on whoever
trounced him, which is a crazy move for one of the world’s most
competitive people, but he promised.
“You know what’s amazing to me?” Sheekey asks, somewhat rhe-
torically, as we talk in mid-February in a conference room domi-
nated by a TV with CNN on mute. “I was just talking to somebody
who worked for Hillary for a really long time. I said, ‘Where do you
want to start? Joe’s campaign’s over.’ She goes, ‘What are you talking
about?’ I’m like, ‘Are you kidding me? What are you drinking? You
don’t come in fourth in Iowa and fourth or fifth in New Hampshire
and go on to win a major party nomination. There’s no historical
precedent for it. What are you talking about?’ ”
And then there were the ads—millions of ads. Positioning him-
self as a friendly new product in the American landscape, like the
Geico lizard, Bloomberg carpet-bombed 50 states with television
ads and even hired female prisoners in Oklahoma to call to voters
via a third-party vendor (the campaign says it was unaware of the
arrangement and halted the contract when it was revealed). Gary
Briggs, the former CMO at Facebook, is running Hawkfish, Bloom-
berg’s main digital-strategy team, which has put 2 billion ads so far
on Facebook and Google. At a scale unprecedented for political
campaigns, which are always playing with so much less cash than
the corporate world, Bloomberg has drafted an expansive, best-in-
class team of Silicon Valley data scientists, social-media managers,
and even executives from his own company, “some of whom are
true believers in Mike and trying to save the Republic and some of
whom were not really given a choice about joining the campaign,”
says a former colleague. “He’s working them like dogs, and they’re
like, ‘When can I go back to my nice corporate job again?’ ” (A cam-
paign spokesperson says no employees were forced into a job.)
Bloomberg, a believer in open-plan offices, sits in a quiet corner.
His head pokes up over his desktop computer, partially obscured
by a vase with yellow daffodils. One ex-employee describes getting
into a fight with Bloomberg and, regardless of whether Bloomberg
has an executive suite in his offices, hearing him bark: “ ‘Don’t forget
whose name is on the front door.’ It’s ridiculous,” he says. “Mike’s
name isn’t only on the door; it’s on the fucking pencils.”BEYOND THE MANAGEMENT SKILLS, those who know
Bloomberg call him a sun god—when he’s shining on you, all is
bright, but wait for the shadow. In Providence, he stands in front of
a crowd of a couple hundred in a fancy new civic building dubbed
the “Innovation Center” to deliver his usual stump speech to crowd
of mostly white professionals (afterward, I talk to a therapist, a
retired engineer, a designer of logos at CVS, and several professors).
As they hold up their cell phones to capture the historic moment of
a presidential candidate in the flesh in their small and not-at-all
electorally important state, he drones on and on. He speaks in
monotone with such a flat affect that one’s brain almost cannot
process his words as language, but rather white noise with a soothing
background whisper of “We’ll do lots of things, it will be great.”
Here and there, he usually tells some jokes. “People say, ‘Do you
really want a general election between two New York billionaires?’
To which I say, ‘Who’s the other one?’ ”
Directly to Bloomberg’s left, a bunch of tattooed guys wear-
ing black leather bomber jackets, looking vaguely like the band
Foreigner in Red Sox caps, start hollering. “Can you tell us why