How Bloomberg Won First Race as Billionaire Underdog

Michael R. Bloomberg was not entirely picky. By the late 1990s, financially megasecure and professionally restless, the billionaire businessman had told friends that four jobs on earth could tempt him away from his company: president of the United States, secretary-general of the United Nations, president of the World Bank and mayor of New York.

And several months before Bloomberg announced his 2001 bid to fill the looming vacancy at City Hall, some of those friends were worried about him. One of them, Sen. John McCain, sent word to the sitting mayor, Rudy Giuliani, asking him to talk Bloomberg through the grim realities of what even some aides viewed as an electoral suicide mission.

Giuliani agreed. “You’re going to lose,” he told Bloomberg flatly during a meeting at the mayoral residence, Gracie Mansion. This position was sensible. Bloomberg, a rhetorically challenged political newcomer and longtime Democrat, would be running as a Republican in a Democratic town that had grown weary of its Republican incumbent.

The warning was of no use. Bloomberg had been paying people for months to explain these risks to him. “The next morning,” he often said privately, imagining the day after a defeat, "I'm still better off than the next guy."

He entered the race in June, three months before the Republican primary, appearing so stiff at an introductory news conference that a reporter had to instruct him on how to proceed. “That’s not going to stop, no matter what I do?” Bloomberg asked anxiously as cameras clicked.

He never improved much as a candidate. By January, he was mayor anyway.

Nearly two decades later, as Bloomberg plots an unconventional path to the Democratic presidential nomination, allies see his first mayoral run as proof of concept. It was the race that demonstrated, to Bloomberg and to those who might doubt him, that an inelegant campaigner with bottomless resources, party agnosticism and a heap of political baggage could prevail.

Then as now, he was prepared to spend whatever it took — some $70 million in 2001, a figure he is expected to greatly surpass in 2020 — to burnish his name and bury his opponents. Then as now, those urging him to reconsider were brushed aside, overruled by a man at once fanatical about data-driven decision-making and secure in the knowledge that statistical unlikelihood had never stopped him before.

Yet a review of the 2001 race, drawn from dozens of interviews with aides, advisers and adversaries, makes plain that Bloomberg’s political origin story owes to almost supernaturally improbable conditions — a blend of searing tragedy, canny check-writing and a string of flukes so politically fortuitous that his Democratic rival began wondering if the New York Yankees were conspiring against him. (The team’s World Series appearance that fall, stretching a full seven games and extending into November for the first time in history, allowed Bloomberg’s final advertising blitz to be broadcast before an outsize local audience just before Election Day.)

By far most significant, the shock of the Sept. 11 attacks conferred instant resonance upon Bloomberg’s message of steady-handed management, which had stirred limited enthusiasm initially. “On September 10th, 2001, the city was doing well. There was no compelling need for an outsider,” said Edward Skyler, a campaign aide in 2001 who became one of Bloomberg’s deputy mayors. “A career politician would do fine on September 10th.”

In a flash, the October endorsement from Giuliani, the lame-duck leader suddenly elevated to temporary political deity, also became the highest of municipal blessings.

To this day, Bloomberg, 77, is sensitive to any suggestion that he took office as an accidental mayor, elevated by external forces and a predecessor with whom he was never especially close — particularly after Giuliani’s rightward lurch in recent years. Bloomberg has long insisted to associates that he triumphed primarily because of the unpopularity of the Democratic nominee, Mark Green, a liberal former public advocate. But even admirers attribute his success in large measure to the attacks, Giuliani’s support and a racially divisive Democratic primary.

Veterans of the race tend to say that there were two campaigns in 2001: before the 11th and after.

“He got the benefit of the doubt in that moment that he wouldn’t have gotten,” said Randi Weingarten, the teachers’ union leader, with whom Bloomberg met repeatedly as he explored a run.

And so, too, it seems, were there two Bloombergs: the one who decided he might like to be mayor and saw no harm in trying — and the one, 18 years out, disinclined to remember a world where he almost never was.

The Career Switch

Bloomberg scanned the boldface roster of charity ball committee members and wondered.

“How do you get to be on one of these lists?” he asked an acquaintance, a half-dozen years before entering politics. In short order, he became the kind of person on all of those lists: nonprofit boards; cultural organizations; society affairs he hosted himself, in his Paul Stuart dinner jacket and red bow tie.

Friends saw this period as the first signal that Bloomberg’s business-information empire no longer enchanted him fully. It was also an early template for his courtship of the institutional powers — civic leaders, editorial boards, party officials — that could grease a campaign.

Bloomberg often said he intended to bounce a check to the undertaker. And as he moved toward a run in 2001, he appeared ready to make good on the promise.

In public, he would broadcast ads trumpeting the more than $100 million he donated to various philanthropies the year before, including Gay Men’s Health Crisis and the Committee to Protect Journalists.

In private, top-dollar advisers came aboard to synthesize reams of polling and focus group data. Policy experts were summoned for briefings at his company headquarters. Aides were tasked with drilling him, pop-quiz-style: What’s the cost of a subway ride? The price of a gallon of milk?

Touchy about being caricatured as a flighty tycoon, Bloomberg bristled at any implication that he was flirting with a run for the attention. “How can anyone think I’m not running?” he asked privately months before formally entering.

By the spring, he had leased a campaign office in midtown, stocking it with signature flourishes of the Bloomberg brand: an open-plan layout, unlimited snacks and a young, hard-charging staff.

Quickly, some uncomfortable alliances were deemed necessary. Bloomberg, who had determined he could not survive a crowded Democratic primary, won the backing of many Republican officials with the promise of self-funding, despite his socially liberal views.

And because of New York’s unusual voting laws, which allow a candidate to appear on multiple ballot lines, Bloomberg also cast his eye on some fringier political elements. He gave money to the city’s Independence Party, whose support he would seek amid a rolling controversy over some of the group’s leaders. (These included an activist who once called Jews “mass murderers of people of color” and a psychotherapist who had promoted sex among therapists and patients.)

In addition to television spots, Bloomberg blanketed small community papers in several languages, purchasing ad space and goodwill in equal measure. Pro-Bloomberg VHS tapes were mailed to individual voters. “He’s a firm believer in bringing a gun to a knife fight,” said Bill Cunningham, a top adviser on the race.

Bloomberg, unfamiliar with most neighborhoods outside Manhattan, seemed to enjoy getting acquainted. He remarked that some quieter corners of New York reminded him of his native Medford, Massachusetts. He called his mother every day with updates on his whereabouts (“Here I am in Brooklyn!”) and gamely stepped behind the grill to flip sausages at block parties, his polo shirt tucked in.

In younger company, Bloomberg smiled often through a favorite bit of physical comedy: high-fiving children before pulling his hand away, leaving a youngster to swat at the air.

“The untold story of 2001 is that Mike campaigned from 7 a.m. to 10 p.m. every single day,” said Vincent La Padula, another campaign aide.

But Bloomberg could grow frustrated with the attendant scrutiny, at times showing indiscipline as a first-time candidate. He wondered aloud whether Fernando Ferrer, a Hispanic Democratic mayoral contender, was a baseball player. He invited outrage over comments favoring public school prayer. He chafed at questions about his finances. Asked once why he had not released as much tax information as his peers, Bloomberg snarled, “They don’t make anything.”

Several news stories detailed sexual harassment lawsuits at Bloomberg’s company and a booklet of off-color sayings given to him once as a birthday present, copies of which were distributed gleefully around City Hall by a young Democratic congressman and future mayoral hopeful, Anthony Weiner.

After a Daily News article during the campaign cast doubt on Bloomberg’s account of being rejected for Vietnam military duty — questioning the timeline and circumstances of his being turned away for having “flat feet” — he had read enough.

“Take me home!” he instructed his driver, seething, midway through the day’s campaign schedule, according to a person present. Aides persuaded Bloomberg to keep making his planned stops.

Other dust-ups were more confusing to him than maddening. In one speech, he suggested offhand that sanitation workers had a more dangerous job than police officers — strictly true, according to a statistic he had been given about on-the-job hazards. When police union leaders responded with fury, Bloomberg seemed taken aback, unwilling to concede that even a technically accurate statement may have been politically unwise.

“Very few people I work with want to be told what to say, but they do want to be told what not to say,” said Frank Luntz, the pollster and consultant who advised Bloomberg in 2001 and speaks fondly of him. “Mike didn’t want to be told anything.”

But as the summer wound down, Bloomberg appeared poised to win his Republican primary against Herman Badillo, a former congressman and deputy mayor, even if he remained a long shot in the general.

On Sept. 10, the night before the scheduled primary, Bloomberg closed by presenting his campaign as the answer to a citywide political emergency.

“How do you write September 11?” he asked Republicans on Staten Island. “9-1-1!”

The Primary Day

Nobody knew quite what to do. So Bloomberg showed up at a blood bank.

Three of his employees and the brother of a campaign aide were missing. The primary was postponed — all political activity was suspended — but no one much worried about that. Bloomberg had donated one of his company’s spaces downtown for emergency workers seeking food.

At the blood drive, the day after, an NBC reporter spotted him. Was it important, Bloomberg was asked, for the city to see its leaders performing deeds like this?

“I don’t know that it really does anything,” he said. But that was Bloomberg: unsentimental even when he cared.

And in the weeks that followed, with the election looking more winnable, former aides say Bloomberg approached the race with a sharpened sense of purpose. “I want it now more than ever,” he said, according to Cunningham.

Bloomberg easily won the Republican primary, rescheduled for late September, and a quarrelsome runoff on the Democratic side helped his cause, pitting Green, the former public advocate, against Ferrer, a Bronx borough president whose supporters included the Rev. Al Sharpton and Donald Trump.

After Green secured the nomination, Bloomberg signaled quickly that any political cease-fire had passed. “I am a professional manager,” he said. “He is a rookie.”

The tragedy had scrambled not only the contours of the race but also several lower-order practical and logistical considerations, almost exclusively to Bloomberg’s benefit. The dominant focus on the disaster’s aftermath left little news media oxygen for the election, sparing Bloomberg from deeper vetting and increasing the relative value of his airwave-clogging paid media strategy. And that spending, in turn, affected the wider advertising market, inflating rates for Green.

Then came the Yankees’ marathon postseason, which persisted until two days before the election.

“Ugh, the seventh game,” Green said in an interview, recalling the ubiquity of Bloomberg’s spots during the World Series, which the Yankees ultimately lost. “I don’t want to be disloyal here, but I remember thinking, ‘Wait, is every domino falling?’”

Both camps could see the race tightening in the closing weeks. But Bloomberg still had an unwieldy coalition to herd: He hoped to embrace Giuliani, whose video endorsement of Bloomberg was among the ads in heavy rotation, while appealing to Democrats who had thought little of the incumbent over most of his two terms.

Bloomberg won the support of two prominent Democrats, former Mayor Edward I. Koch and former Gov. Hugh L. Carey, and spoke bluntly about his come-lately Republicanism, alienating George Pataki, the state’s conservative governor, at a joint appearance.

“He said he was a liberal six times,” Pataki said of the event. “‘I’m a liberal. I’m a liberal. I’m a liberal. I’m a liberal.’” By the fourth “liberal,” Pataki said he began shuffling away a bit.

The Next Mayor

All the while, the more traditional liberal in the race could not stay out of his own way.

In Green’s zeal to project readiness for the job, he had committed a cardinal sin of the moment — appearing to diminish Giuliani — imagining that he would have done “as well or better” leading the city after Sept. 11 if given the chance.

Bloomberg’s team cut a devastating ad, punctuating a reel of the Democrat’s own comments with a single word written on-screen: “Really?”

At least as significant, Bloomberg and his allies capitalized on fissures dating to the primary between Green and Ferrer, flowing in part from the distribution of anonymous flyers in predominantly white neighborhoods depicting a tabloid cartoon of Ferrer kissing Sharpton’s rear end. Ferrer’s camp blamed Green. The tensions created an opening for Bloomberg with black and Latino voters, and Sharpton pointedly withheld an endorsement of the Democratic nominee.

While Bloomberg never expected to earn Sharpton’s support, the campaign took care to remind him that Bloomberg planned to open a dialogue if he won, a sharp departure from Giuliani’s attitude.

“He’s not a manipulator, but he’s a great reader,” Sharpton said of Bloomberg in an interview. “He can read a scene very well.”

The Bloomberg campaign ran radio ads criticizing the flyers and connecting them to Green on stations with big African-American audiences. The candidate’s investment in the Independence Party also paid off: Jacqueline Salit, a party leader at the time, said the group urged black residents to “use their vote as a protest against Democratic Party manipulation” by supporting Bloomberg on the Independence line. His vote total on that line would exceed his margin of victory.

Several prominent Democrats strained to strike a fragile peace between Green and disaffected black and Hispanic leaders, prompting private appeals for party unity from Green supporters like former President Bill Clinton and Harvey Weinstein, the not-yet-disgraced movie producer, in an eleventh-hour bid to keep a Republican from office.

In the end, Bloomberg earned about half of the Latino vote and a quarter among African-Americans, far exceeding typical Republican showings. He won by fewer than 3 percentage points overall.

It has not been lost on civil rights activists that the man who would ultimately use his post to expand and aggressively defend stop-and-frisk policing in communities of color came to power, in large part, with their help. “It’s ironic,” Sharpton said.

Still, as early returns dribbled in on election night, nothing seemed guaranteed. Inside his midtown hotel suite, Bloomberg cautioned against overconfidence, setting expectations for his 92-year-old mother, Charlotte. “He said to her, ‘Listen, I’m probably going to lose,’” Cunningham recalled. “‘But it’s going to be really close, so I won’t be embarrassed.’”

Aides scribbled vote tallies on napkins. The initial numbers showed Bloomberg behind, but Staten Island, the Republican bulwark, was still coming in. By midnight, the math was clear.

“I didn’t jump up and down cheering, I can tell you that,” Bloomberg told a biographer years later. “That’s not me.”

He walked across the street to address his victory party at a jazz club. Giuliani stood behind him, picking confetti off his shoulder and raising a chant of “USA.”

Bloomberg smirked a little.

“The easy part is done,” he said. “Now comes the hard part.”

Matt Flegenheimer and Maggie Haberman c.2019 The New York Times Company