march 2–15, 2020 | new york 27Bloomberg’s not asking for donations for his campaign—though
he’d prefer his friends, the donor class, didn’t give other candidates
money either. This is appealing to some folks, but not all. “How
much is Mike worth?” says developer Douglas Durst. “A lot of that’s
thanks to Trump’s tax policies. So he’s using the money Donald gave
him to run.” Durst adds, “He doesn’t need my money. I’m going to
support whoever the nominee is.” Even those who may like Trump
regard Bloomberg as a civilized alternative: “Donald has done much
that will be perhaps considered positive in the future, but he polar-
izes people,” says Cancer Research Institute trustee Lauren Veronis.
“Calling him ‘Tiny Mike’—well, the people who like Mike get their
shoulders up about it.” I ask Emma Bloomberg about the young
moneyed class in New York, which, from my casual survey, seemed
split on supporting Trump. She mentions being at a couple of dinner
parties with friends of hers or her dad’s this summer and having “the
question [at the table] be, ‘If it’s Trump or Warren, who do you vote
for?’’ The number of people who, if you ask them on any individual
policy or social policy, are vehemently anti-Trump, who would say,
‘Well, in that case, I’d have to sit it out,’ or in that case, ‘Yes, I’d have
to vote for Trump,’ I found astounding.”
THE EARLY STAGES OF THE CAMPAIGN FELT,internally,
relatively smooth—the race evolving exactly as Sheekey and
Wolfson had hoped, the media desperate to believe in the glow of a
Bloomberg candidacy. But the same day as the New Hampshire
primary, the first bit of oppo dropped: an audio clip about stop and
frisk from a Bloomberg talk at the Aspen Institute several years ago.
As the story gained steam the next morning, it just so happened
some black faith leaders were at HQ for a meeting when Trump
tweeted out that Bloomberg was a “total racist.” “The phones of
Mike and the faith leaders in the room kind of lit up,” says Sheekey.
“Twenty-four to 30 faith leaders around the table’s instant reaction
was, ‘We have to do something. We need to call a press conference.
We need to endorse Mike Bloomberg now.’ ”
To friends, Bloomberg insists he feels bad about stop and frisk,
but he still can’t understand why he’s not gathering applause for gun
control. “Mike came into the mayor’s office, black people were dying,
and he was like, ‘God almighty, how do we solve this,’ ” says a friend.
“What he says privately is, ‘I was sitting with mothers of boys who
were being shot. They said their sons were scared in the projects and
had guns to protect them, so I thought you’ve got to get rid of the
guns. The guns are killing people.’ But he didn’t get the social impact
of stopping kids 70 times in high school.” They say he understands
the humiliation now—mostly. He’s also a little “Asperger’s-y,” friends
say, meaning he doesn’t quite feel others’ pain.
Then the Washington Post got its hands on a booklet of “Wit and
Wisdom” Bloomberg’s employees had put together to celebrate-
slash-roast their boss in 1990—a pamphlet actually located by Fire
and Fury author Michael Wolff for this magazine in 2001. “I wrote
about it on Monday, September 10, and the next day, the story was
forgotten,” says Wolff. “The towers were crumbling and I’m going,
‘My scoop, my scoop!’ ” Bloomberg’s grotesque alleged phrases
pinged around the world, along with the old news that he’d told
an employee newly pregnant to “kill it,” which is quite a bit of dry
humor indeed.
When I ask Wolfson about Bloomberg and women before the
first debate, he waves questions off. “Allegations, news reports,” he
says. “There’s no one who runs for president who doesn’t have to
deal with some negative information that’s disseminated or
reported upon—that’s table stakes, that’s my day at the office.” Tay-
lor was reportedly even more unemotional: “It was 30 years ago,
get over it.” But misogyny is another case where Bloomberg seems
to kind of get it and kind of not. He has argued that in the case of
Charlie Rose, whose TV show taped in his corporate offices and
who, according to two individuals, did not pay rent, courts should
decide. He has many capable women around him, yet he’s known
for making lascivious comments that are totally out of bounds.
Ginny Clark, the first woman in Salomon Brothers’ training class,
sat next to Bloomberg in 1968, and considers him a mentor. “The
things that happened to me,” she says, trailing off. “Honestly, I’ve
never sued through my whole life, or never wanted to, because I
felt I will rise above it, which luckily I always did. You know, today,
for a hug they’ll sue you.” Clark paints a picture of the stockbrokers’
lifestyle of yore—an in-office barbershop and waiters in black tie
bringing around lunch on china so traders never had to leave,
people who would “slam phones, scream, yell, strippers, you name
it, it would go on.” What did Bloomberg do during all of this? “I
won’t tell you some of the things they tried on me, but it wasn’t
Mike—it was some of the others. He was there, kind of like making
them back off some,” she says.
As the oppo fell from the sky like rain, true believers tried to
spread calm. “Mike inspires incredible loyalty,” says Dan Doctoroff,
one of his lieutenants for years and the founder of Sidewalk Labs.
I also talk to Fatima Shama, Bloomberg’s commissioner of immi-
grant affairs. Wearing a lanyard with an i like mike button, she
describes creating the “culture that is Bloomberg” at HQ, with its
grab bag of politicos and social-media managers from all walks of
life. “I have said to people here who have had an abrupt tone, ‘Try
again.’ And they’re like, ‘Excuse me?’ And I say, ‘We don’t speak to
people that way here. Try again.’ ”
On the campaign, Shama leads outreach to minorities and
women as the head of constituencies and coalitions. But would
Sanders take better care of these folks? “There’s no record of Sanders
ever doing that,” she says. She calls Mayor Pete a “38-year-old who➞Mike 2020 swag.