march 2–15, 2020 | new york 23campaigns in our history. Bloomberg’s case, beyond climate
change, gun control, and urban renewal, rested on an electability
argument—that defeating Trump was an absolute necessity and
that a technocratic moderate was a safer bet than a democratic
socialist. But in the space of two weeks, his campaign had seemed
to damage moderate Biden’s prospects and dramatically elevate the
temperature of conflict between the party’s progressive and Wall
Street wings, all without managing much headway on his own
candidacy. By the end of February, the ride looked to be about
over—or at least poised to come to a halt on Super Tuesday, after
two weeks of pile-ons from Elizabeth Warren and Bernie Sanders,
an increasingly ugly and almost unending archive of oppo research
(previous comments about how cops could Xerox pictures of
minorities to find criminals or suggesting Mitt Romney would be
a better president than Barack Obama) and an absolutely dead-
eyed first appearance before a national audience, in which
Bloomberg didn’t seem to have anticipated needing to answer any
of the most obvious criticisms and whiffed his jokes. But in between,
for a brief and glorious moment, it had looked like the New York
power and media elite, who are Bloomberg’s natural base, might
actually have their way, taking the most important presidential
election of any of our lifetimes into their own hands—and collecting
some huge consulting paychecks in the process.
Bloomberg officially announced his candidacy on November 24,
signaling immediately that he’d skip the first four states and just
focus on the races beginning Super Tuesday. The Iowa-caucus
counting app blowing up on February 3 was the stroke of luck
Bloomberg needed to move up in the polls, after which he smartly
capitalized on the chaos by doubling his ad spending (“Obviously a
flex,” as one of his staffers jocularly put it to me). Bloomberg had bet
on no clear front-runner coming out of Iowa, then Biden getting
soft, then the moderate lane falling apart, then Sanders or Warren
arising as the default victor, then a collective buyer’s remorse that
would allow him to swipe the victory out of his or her hands. But this
was better than in his dreams. And it came so cheap! Bloomberg’s
self-funding was $5.6 million per day. Given that Bloomberg’s for-
tune earns $107 million per day, according to the Washington Post,
he could comfortably go a lot higher still. (Biden, then the putative
front-runner, had raised $8.9 million in all of January.)
Before the Nevada debate, some aides had put out the word that
even if Bloomberg performed poorly—which he would, they said, so
please lower expectations—the moderate wing of the party should
line up behind him, given his money spigot and all. He had publicly
floated the idea that he might spend $1 billion on the November
election whether he was the nominee or not. Whispers within the
campaign suggested his actual ceiling was $4 billion. By the end of
the month, it seemed he might have to spend that much to save the
party from the disarray he had himself helped create, in part by
complicating the candidacy of the one moderate who actually had a
shot, Biden, while clearing the way for Bernie to march to the nomi-
nation with 35 percent support.
Until the debate, the question on everyone’s minds had been
“Can the presidency be bought by the ninth-richest man in the
world?,” to which the answer seemed to be “Yes, possibly.” He had
even briefly managed to turn the caricature into a sort of strength,
at least for niche audiences, churning out a raft of weird social-
media memes that it took the internet’s cool kids a few days to
figure out but that amounted, ultimately, to Mike leaning into a
reputation as an out-of-touch moneybags. But that was a kind of
managed image, and the debate was disastrously unmanaged—as
was the South Carolina reprise, though measurably less embarrass-
ing. Afterward, the question became “Can the presidency be won
by someone with negative charisma?” The answer to that was much
less certain. After all, Trump performed a similar end run around
the Establishment in the last presidential election, but he also knew
how to command the camera, and who could stop rubbernecking
whether one regarded him as a demigod or car crash?
So why did Bloomberg run? Love or hate him, he is an exceed-
ingly rational creature, and, over the summer, his team identified
a teeny-tiny crack in the door that opens to more power than any-
where in the world—about a 5 percent chance of gaining the
presidency, I’d heard—and thought they’d try to wiggle through.
Bloomberg had been under the impression that Biden had the
moderate lane covered when he declared that he was skipping a
run in March 2019. But Bloomberg spent the summer in the
dumps (golfing, grandkids, no longer jogging but doing a lot of
speed walking), increasingly anxious about another four years
under the thumb of a man who had been the laughingstock among
his elite friends for decades upon decades. Try to put yourself in the
shoes of a $60 billion ego: If one had Bloomberg’s fortune, and
Bloomberg’s resolve, and did not at least try to destroy the Cheeto
with his own bare hands, what would that mean to history? Trump
worked against the cause of progress, Trump was bad for the
planet, Trump was a threat to rationalism, Trump revealed his
indecency in Charlottesville, and who knew what terrifying animal
spirits he’d stir up next? “Mike once said to me, ‘The only way the
Republicans abandon Donald is if he fucks a child or wakes up in
bed next to a dead person,’ ” says an acquaintance, putting his spin
on Louisiana governor Edwin Edwards’s famous old line. The cam-
paign responds, “Mike does not remember saying this.”
Throughout 2019, Bloomberg, like many older politicians also
feeling their mortality, John Kerry among them, watched as War-
ren became the presumptive nominee, then faded, and looked
again at Biden and thought, How is this guy this bad, and this
broke, and still winning? For years and years, Bloomberg had an
apparatus continually monitoring his chances—maintaining, just
as a kind of casual, on-the-side, not-so-serious exploratory team,
as big a campaign as most candidates would have as they
approached the Iowa caucuses. He also gathered intelligence anec-
dotally, canvassing his clique. “We had a couple pretty long conver-
sations, with me quizzing him and him trying to get an evaluation
for what the odds were,” says Brokaw. “The more he looked at it, the
more he thought, I do have a shot. And the more he felt a civic
obligation.” “My dad often tells me regret is not an emotion that he
has,” says Emma, Bloomberg’s
elder daughter. “I’m not sure
how that’s possible!” But the
interregnum between saying
he wouldn’t run in March and
then declaring he would
indeed run in November was
“the first time in my life that I
would have pushed back,” she
adds. “I would’ve said, ‘I think
you regret making the deci-
sion not to run.’”
When Bloomberg first
announced, facing what
seemed like such steep odds
Nate Silver was reluctant to even list him among the serious can-
didates, Democratic insiders suggested that Bloomberg’s team may
have sold him a little hard on his prospects, making his shot sound
more probable than it was. And Bloomberg’s campaign manager,
Kevin Sheekey, regarded as a master of the dark arts and one of the
hardest-charging political operatives in the country, did donate
$2,800 to Biden, the maximum personal contribution, as recently
as June. But within months, Sheekey, a baby-faced guy regularly
clad in a baby-blue open-collared shirt (“I literally look at people
with ties, even in movies or photos, and think,Who came up with
that, and why do you wear it?”), was back on the Bloomberg train.“As my unclesays, ‘Rich orpoor, it’s goodto have money.’”