26 new york | march 2–15, 2020bookkeeper from Medford, Massachusetts, with a job as a parking-
lot manager to pay tuition at Johns Hopkins who then attended
Harvard Business School. Shocked and intimidated by the inherited
wealth at HBS, he felt more comfortable on Wall Street. He loved
New York, taking an L-shaped studio on the Upper East Side listed
for $150 a month that he bargained down to $120. He went to Max-
well’s Plum, the singles bar where Donald is rumored to have met
Ivana, and told this magazine he spent his vacations on his apart-
ment building’s roof—“tar beach.”
Bloomberg made his billions in an unsexy business: database
terminals for the Wall Street bond market. Though his company,
of which he owns 88 percent, expanded into many areas, including
media, it remains a data-processing and terminal company. “Mike
destroyed every competitor in the terminal game to become a
monopoly,” says a former employee. “The terminal is a status
symbol—Bloomberg-terminal fanboys rival Apple fanboys and
Tesla fanboys.” And while that makes Bloomberg himself a tech
mogul, he no longer really plays the part. “If Mike had a problem
with his computer or phone, the entire engineering team would
run over to his desk,” says an ex-employee. “Then they’d be like,
‘You need to put your phone on Wi-Fi.’ ” After expanding into the
news business, he worried over the font size on TV chyrons and
exhibited only a cursory awareness of the internet. (His campaign
counters that Bloomberg is “deeply aware of technology trends.”)
Long-term employees say he seemed to have lost a step when he
returned to the business from the mayoralty in 2014, lobbing the
notion he should cease publishing a website and saying he was
against advertising. An employee argued for ads, saying, “ ‘Well,
Mike, what if you were reading, like, a golf magazine and saw some
clubs? You might think these are worth getting.’ He was like, ‘No,
I’d just ask my golf pro what the best club is.’ ”
It’s incredible that in 2020 anyone still needs a $24,000 dedi-
cated Bloomberg terminal to gather corporate information and
trade stocks, but apparently they do. A friend says Bloomberg mostly
socializes with the buyers of big terminal orders at banks and old
friends, and he even maintains a relationship with Jeff Bezos, whom
he likes quite a bit (Bloomberg was privately appalled that New York
City wouldn’t let Amazon into
Queens, though he also sug-
gested the deal was too gener-
ous to the company). A devout
kibitzer, he’s a funeralgoer,
wedding-speech-maker, and
I’m-calling-the-top-oncolo-
gist-for-you-er who keeps in
touch with many from his
past, even those from high
school who have fallen on
hard times; they hit him up for
money, which he finds stress-
ful. But he does dole out. At a
New York City fund-raiser, “I
was in front of the crowd, waf-
fling on about trees, saying, ‘I
always had this dream of
planting a million trees,’ ” says
Bette Midler. “Suddenly, Mike leapt to his feet and shouted, ‘That’s
a great idea! We’re going to do that!’ Everyone stared, aghast. Three
beats later, thunderous applause, and a standing ovation, because
the whole crowd knew that if he said it, it would get done. And it did.”
As mayor, he famously chose not to live in Gracie Mansion,
preferring the comforts of his 79th Street compound, though not
everyone is impressed by his old-world décor: “The first time I
went to Mike’s house, I was surprised to find the décor very much
like a child’s idea of what a rich man’s house would look like,” saysan acquaintance. “Very Citizen Kane.” He kept his social life
mostly intact, spending weekends golfing at his home in Ber-
muda. “Mike gets loosey-goosey on wine, visibly shining, but if you
really try to get him to open up then, sure enough he gets flustered
and retreats into his shell,” says a reporter.
Bloomberg’s children, Georgina and Emma, are opposites. Geor-
gina, 37, is an equestrian and private-plane-flying Instagram bomb-
shell who, when her dad said he wasn’t going to run for president
in March, posted a picture of a faux campaign sticker, reading
bloomberg: because fuck this shit, with the caption “officially
back to being just our family slogan.” She has lots of animals: “We
have a 300-pound pig,” says Mike Bloomberg. “We have a goat who
tries to put his horns in your pocket and rip your pants open. We
have a pigeon that just moved in, but we also have a rooster who
wakes you up early in the morning. We have a mule. We have some
horses. Stop me when you get bored.”
Emma, 40, is a policy wonk who runs an education nonprofit.
When I meet her in a hotel lobby near Bloomberg HQ, she’s all
Tribeca-mom elegance: her brown hair slightly lightened, arms
sculpted, and many tiny diamonds adorning her ears and climbing
from wrists to forearms. Donald has famously declared he never
changed diapers; Bloomberg, ever the egalitarian, didn’t like feed-
ing infants, so took as his solemn duty changing diapers instead.
Emma knows Ivanka—they were in an after-school art class in
middle school together—but she doesn’t remember her dad talking
about Donald Trump before he became president. “I cannot
remember ever hearing of him,” she says. “He’s not going to be
happy about that. I’m sure he’s supposed to be the subject of every-
one’s dinner-table conversation.”
Unlike the Trumps, whose family unit was forged in Donald and
Ivana’s miserable marriage, Bloomberg and his ex-wife, Susan, had
an amicable divorce in the ’90s and even lived together at times
afterward. “People can love each other, can be dear friends, can be
supportive of each other in lots of ways and not be meant for
marriage—they were very clearly not,” says Emma. “My mother
wanted to stay at home, and my father had to be out. As a child, just
because you’re young doesn’t mean you’re an idiot, right? You actu-
ally do see these things and internalize them.” After the divorce,
Bloomberg tomcatted around town and made many comments
about women’s figures not at all under his breath. The campaign has
recently been rolling out his longtime partner Diana Taylor, 65, a
lifelong Republican from the heartland of Old Greenwich, Connecti-
cut, who became a Democrat in 2018. Taylor attended Milton and
Dartmouth, started at Smith Barney in the 1980s, and has been New
York’s state superintendent for banks. Anna Wintour calls in dresses
for her, she loves her Labradors, and she’s on the boards of Citigroup
and a micro-lending nonprofit.
This genteel lifestyle—Bloomberg’s planes aren’t very chic, says a
friend, “though they have four”—is a direct contrast to the patriarch’s
salty language. “His humor is dry, almost too dry, and sometimes it’s
over the line,” says Brokaw. “I would say I probably learned every
curse word I know from my father,” says Emma. “I have vivid memo-
ries of the expletive, expletive, slam!” She pantomimes hanging up
a corded phone. “But he never used them at me or with me. That was
how he got his stuff done.” Even at his home, during carefully com-
posed dinner parties, he can get touchy. Long ago, during his quest
to build a stadium on the West Side, conversation naturally turned
to the viability of the project. “I asked a question, as one does at a
cocktail party, revealing my personal concerns, and was startled
when he interrupted me with the harsh admonition, ‘You have no
idea what you’re talking about,’ ” says the head of a nonprofit. “It was
a really bizarre moment. I was a guest in his home. Mike was not
only not interested in engaging in discussion but devoid of basic
manners.” (About this episode, the campaign says, “This person
probably had no idea what he was talking about.”)“You’re a sellout,”
they scream.“Thank you formaking me feellike I was inNew York City,”Bloombergresponds.