The Many Lives of Michael Bloomberg

by Eleanor Randolph

  By the time he was hinting that he might run for mayor, the New York Post had labeled him the anti-bimbo billionaire, and Bloomberg’s explanation for his maturing tastes in companions was that he had tried the Wall Street world of girls, girls, girls and decided older women were a better option. “I find women my age more interesting, I guess. Maybe it’s just that I have less in common with younger women. It’s also safer. Somehow or other, the wives of your friends find it much more reassuring.”16

  * * *

  Indeed, he always seemed to be keeping his options open. He scoffed at the idea of getting married again, and even enjoyed teasing anyone who was getting married about the hazards of legalizing a relationship. He professed to like the freedom of knowing he could stray when he wanted.

  Despite his very vocal anti-marriage stance, Bloomberg would spend most of his mayoralty and post-city years with Diana Taylor. Taylor, a financial executive, was beautiful, scary slim, gracious, intelligent, and dressed like someone straight out of Anna Wintour’s wardrobe room at Vogue. A graduate of Dartmouth with an MBA and a degree in public health from Columbia, she was widely viewed in New York’s social circles as “a catch for any man, no matter how powerful,” as one of Taylor’s social peers put it.17

  Yet too often Bloomberg seemed to treat her like a politically appropriate appendage, as far as some of his friends, especially female friends, were concerned. They talked of painful dinners with Bloomberg using Diana as a foil for his heavy-duty humor. Mostly, in public, he gave her an easier time, and she was a perfect substitute first lady for his time as mayor—always there, smiling at even the most tedious public event.18

  Once, shortly after he left city hall, Bloomberg was asked why he had returned to the top job running Bloomberg LP. “Well, the alternative is for me to stay home every day and talk to Diana about feelings,” he told a Bloomberg television audience that laughed nervously. “If that doesn’t get you back to work, I don’t know what would.”19 A joke, but ouch.

  Any such militantly unmarried male over thirty-five in New York City could raise a few questions and some latent hopes from the gay community, and Bloomberg, even when he was nominally a Republican, supported gay marriage and civil rights. But simply watching him work a crowd might have helped dispel such notions. Once, after accepting an award at a gala for the Citizens Union public interest group in 2013, Mike Bloomberg spotted a tall blond woman in a small huddle of people. The mayor maneuvered himself so that as he passed by the makeshift receiving line, he could give her a hug, a kiss on each cheek. Then he moved a little to shake hands with a few admirers. Then he came back to the blonde. Another hug, two more kisses. He even seemed to be angling for a third round when the blonde suddenly moved on. Out of reach.

  Bloomberg worked throughout an era when women evolved from docile or fake-docile homebodies into corporate tycoons, from timid secretaries and lowly assistants to vocal activists for women’s rights. Like many men in his generation, Bloomberg would eventually seem bewildered by the so-called Me Too movement, the army of women who complained about mistreatment and abuse in the earlier times. He would update the company’s rules to protect female employees and make sure they were given premier benefits. But the real test would come when he stepped out of his private company, his private world, to become a public figure. He would soon hire, and depend on, a group of powerful women to help run his campaign and his city.

  8

  RUNNING ON MONEY

  “He doesn’t get bought. He’s the one doing the buying.”

  —Former New York assemblyman Richard Brodsky

  “Why the hell would you want to do that?”

  —Richard Ravitch on hearing Bloomberg wanted to run for mayor

  Michael Bloomberg told his colleagues that if he ever tried politics, he would not be a legislator, not even a senator. He was a natural boss, and he had to be in charge. But he also wrote that, overall, his “impatience with government kept me away from politics. All elected officials should stop worrying.”1

  As it turned out, candidates for mayor of New York did need to worry. When his publisher, John Wiley & Sons, was packaging his autobiography, Bloomberg by Bloomberg, in 1997, the man himself had already begun to make his moves on the city.

  At fancy New York dinners, especially at charity events where his money had turned him into a social and philanthropic superstar, Bloomberg began hinting that he was interested in politics. It was often a question, an invitation to hear encouragement from the moneyed class. “Do you think I should run for mayor after Rudy steps down?” he would ask, trying to make it seem that he had not already decided on the answer.

  New York’s elite swooned at the very idea of a man with experience as a real manager running their city, but the political professionals, the veterans of the city’s mean political wars waged precinct by precinct, saw little more than a rich man’s diversion. Some wondered aloud whether this was simply one more way of advertising the Bloomberg brand.2 Others saw it as a foolish gamble that could only damage his reputation as a successful businessman, an excess of vanity for a man whose considerable assets would, at best, provide a healthy living for campaign consultants.

  Richard Ravitch, a respected city elder who revived New York’s decrepit subway system in the late 1970s, was shocked when Bloomberg broached the subject. Over a private lunch, the gruff Ravitch, who could make a comment on the weather sound like a stormy edict from Mount Sinai, questioned the very idea. “Why the hell would you want to do that?” Ravitch remembered saying. An unsuccessful candidate for mayor in 1989, Ravitch reminded the very private Bloomberg, who ran a very private company, that candidates have no privacy. Their every peccadillo lands on the front page of a tabloid. The media eats politicians, he warned. They will know the family secrets, he predicted. But Bloomberg didn’t seem to care, Ravitch recalled. “Or perhaps he didn’t think it would happen to him.”3

  Bloomberg’s friends also wondered how a man who had wallowed in the money pits of Wall Street could suddenly turn politically respectable. Their pal, who insisted on being called Mike even by underlings at his company, was well known for blurting out whatever crudity or politically suspect idea that came to mind. He was smart and more ethical than most of his peers, but his tough wit straight from the trading floor was too often, well, misunderstood. To the uninitiated, it could simply sound mean, and his jokes could offend—especially women. The claims of inappropriate sexual remarks and harassment of women in his company would begin to seep out as he became more serious about running for office.

  But Bloomberg was very serious. Sometime in the late 1990s, he had decided that nearly twenty years building Bloomberg LP was enough. He had conquered Wall Street. He had become a business media baron. He had made his billions. Now it was time to succeed at something different, he told friends.

  “I thought twenty years at the company, it’s time for somebody else to do things,” he said years later. “A new guy can always do it better.”4 (He smiled when he said that in 2018, recognizing he was still running the company he started more than thirty-five years earlier.) At some point, after all that mentioning the idea to friends and asking for advice, Bloomberg’s name appeared on everybody’s list of possible candidates to run for mayor. His sister teased him, he remembered; making the point that the newspapers had said he was only good enough to be mentioned as mayor, not as a candidate for president.

  Bloomberg laughed it off. Being mayor of New York City was “a better job than even the president’s,” he remembered telling her. “It’s the ultimate political job. You don’t have a Congress to deal with.”

  Also, the city needed his kind of help, he said. “You’ve got a budget bigger than the GDP of half the countries in the world. You’ve got more embassies here than any other city in the whole world because of the UN.” Plus, the man who liked to run things and fix things wanted his city to work. “And I was tired of people saying, ‘Oh. You can’t do things.’ ”5

  Moreover, Bl
oomberg knew his strengths. And his weaknesses. “I’m not an investor. I’m not an analyst. I’m not a consultant. I’m not a teacher. I’m not a writer. I am an executive. I make decisions . . . in government, the president, the governor, and the mayor are executive jobs.” As for details, Bloomberg wanted to hire good people who would bring him the best choices. “We ask [candidates] about policy. But you have other people that do policy. And you don’t know what policy you’re going to need down the road. So to ask you when you’re running what your policy is . . .” He shrugged. “The problems of today aren’t going to be the same problems by the time you get down the road.”6

  Michael Bloomberg, the executive, the decider, the manager, started working toward his new goal with the customary precision and pragmatism of his other expertise, as the engineer. Campaigns are messy, as a rule, and he wanted to begin methodically, even if things couldn’t stay that way for long. First, as always, he hired the best (and often most expensive) people in the campaign business. Patti Harris had already convinced Bloomberg to hire Kevin Sheekey, a handsome, fast-talking political whiz who could spin the dullest detail into a good story. A veteran of then senator Daniel Patrick Moynihan’s Washington staff, Sheekey dazzled almost anybody in his headlights. There was always some question about how many frills he added as he unfurled his latest tableau. But Patti Harris obviously recognized a political force, and Mike Bloomberg spotted a fellow salesman.

  Sheekey, who had been advising the company on the ways of Washington since 1997, was one of the first political people Bloomberg asked about whether he should run for mayor. Never admit you’re not running, Sheekey counseled. With a direct line to some of New York’s best political reporters, Sheekey kept sowing hints that Bloomberg would run to succeed Giuliani. He knew Bloomberg enjoyed the attention, but, like Harris, he also began to worry that this descent into politics was not going to be neat and easy.

  By January 2001, Sheekey and Harris were working hard to talk their boss out of running when Bloomberg invited them to dinner.

  As they sat down, Bloomberg ordered wine, and when it came, he raised his glass. “Okay, if we’re going to do this thing. Let’s toast on it,” he said. Sheekey and Harris were stunned, but as Bloomberg explained later with a grin, “We decided to take a vote, and one vote carried it.”7

  Soon, Bloomberg had hired political strategists like Frank Luntz, who had helped Republicans, and Doug Schoen, who had helped guide President Bill Clinton through his reelection in 1996, and the seasoned pros at Squier Knapp Dunn, known for creating the advertising for Democratic campaigns going back to Hubert Humphrey’s presidential run in 1968.8 Harris had already been making certain Bloomberg met the key people in the city, including those who knew its politics. She also helped Bloomberg hire not only the political bigwigs, but also the intellectual experts on urban matters like Mitchell Moss of New York University, Ester Fuchs of Columbia, and civil rights activist Alan Gartner, a professor at Queens College of New York.

  But, the prize consultant, David Garth, the guru of political gurus who had helped elect mayors and governors, seemed out of reach. Garth had added his magic to the winning campaigns of three mayors—John Lindsay in the raucous 1960s and early ’70s; scrappy, “How’m doin’?” Ed Koch, who brought the city through the eighties; and the current mayor, Rudolph Giuliani. Garth’s television ads were legendary. When Koch was running against incumbent mayor Abe Beame in 1977, the Beame campaign was pleading with voters to let him finish the job. “Finish the job,” Koch sniffed in Garth’s powerful ad. “Hasn’t he done enough?”9

  Garth had sent word he was not ready to take on a losing campaign, even for a winning paycheck. Harris and Sheekey, however, were not ready to give up. They arranged a clandestine meeting at Garth’s chosen spot—the Café des Artistes, an elegant cave-like restaurant with nymphs painted on the walls and some of the city’s most powerful people maneuvering at the tables. Garth was a tough, plainspoken character, part ogre, part wizard. After Harris and Sheekey convinced him to meet Bloomberg, Garth came away with a rough assessment of the candidate: “This guy was in love with himself. He’s a prick, all right? But he also has empathy for people—blacks and Jews, you know? And I never liked the people around him, except for Kevin, who knows politics and Patti, who has excellent instincts,”10 Garth said later. He signed on anyway. It would be an interesting campaign, he told Sheekey, and the money turned out to be better than good.

  Away from the public eye, at least at first, Bloomberg also shifted more of his philanthropy beyond the city’s cultural centers, adding an astonishing seventy-nine organizations, many of them smaller charities and nonprofits in the five boroughs. They included the Doe Fund to help the homeless and the Staten Island Children’s Museum, the Children’s Health Fund to help pay for a “doctor’s office on wheels” for poor children.11 They were worthy causes, of course, but they would also help introduce Bloomberg across the city to make the super-rich new candidate look as generous as he certainly was.

  Not everyone saw charity, of course. Among the most vocal was former New York assemblyman Richard Brodsky, a Democrat from the city’s suburb of Westchester, who viewed the Bloomberg contributions as a form of political largesse. “He doesn’t get bought,” a political hazard for poorer candidates, Brodsky said dismissively. “He’s the one doing the buying.”12

  As the money for the campaign spread into the millions, the city’s political insiders scoffed. They saw the pollsters and the admen, the analysts and the advisers, and even some of the charities, “taking him for a ride.”13

  But Bloomberg was looking at the odds a little like the money managers he knew from Wall Street. What he and his advisers saw was a political assumption that a Democrat would win after Rudy Giuliani’s eight years of arch Republican rule. Every Democratic leader with an ounce of ambition seemed to be eyeing the mayor’s job. The Democratic public advocate Mark Green clearly thought he was next in line. The city comptroller, Alan Hevesi, another Democrat, was making his play for the top job. The Democratic city council speaker, Peter Vallone, was running, so was the Bronx borough president, Fernando Ferrer, who hoped to be the first Hispanic mayor. On the Republican side, Herman Badillo, a former Democratic congressman and star in the Puerto Rican community, was making his sixth run for mayor, this time trying out the GOP line. At age seventy-two, and after losing the race for mayor five times, Badillo was little more than a placeholder for the Republicans, who had almost no hope of holding on to city hall. To Bloomberg, a Democrat, that meant he was in the wrong party.

  So in 2000, Michael R. Bloomberg quietly switched his registration from Democratic to Republican.14

  * * *

  For every successful candidate, there has to be a good answer to this basic question: Why you are running? It cannot be simply ambition, although a good supply of determination is necessary to sustain the hard work of campaigning. It cannot simply be a love of attention, although it has certainly helped the likes of Donald Trump. In Bloomberg’s case, there was another reason. He believed he could run the city better than anybody else. So Bloomberg and his team slowly compiled an encyclopedic wish list of things he wanted to do as mayor. He wanted to keep the city safer, of course, but also healthier. He wanted full control of city schools, a goal other mayors had failed to get. He wanted to improve the business atmosphere, create a central place for information (which became 311), develop more and better housing, help the unfortunate, make the mayor’s office nonpartisan, and generally make the city hum nicely like one of his famous machines.

  His list of promises compiled later by one political staffer, Bradley Tusk, included an astonishing 349 items. (By 2004, Tusk would claim that 211 were achieved, 113 launched, and 25 were reconsidered.15 Tusk estimated that in his first term Bloomberg had launched or completed 94 percent of his campaign goals.) Some were far out of his reach like election reform and renovation of the dungeon-like commuter terminal at Penn Station or imposing congestion pricing on city drivers—
all of which were controlled by a notoriously inept state government in Albany. Some plans were canceled, like requiring public school students to wear uniforms. (They were costly, and other cities had found few benefits from the one-look-fits-all school dress, the mayor decided.)16 One item on the list—to move the city hall press room from city hall to Staten Island—may have been a joke. Even so, it managed to irritate two groups Bloomberg needed—the press and the conservative voters on Staten Island.

  Overall, however, it was a useful political package for that era, especially since Bloomberg could afford to spend $92.60 per vote on ads, promotions, and advisers to sell his competent, entrepreneurial image.17

  As he turned from the finance world that counted dollars to the business of counting votes, Bloomberg started shedding bits and pieces of the high-end existence he had worked so hard to acquire. Shortly before he announced, Bloomberg resigned from several mostly white private clubs that could offend a diverse city. Wall Street regulars collected clubs like personal tokens, and in this way, Bloomberg had followed his pack. He quit the Harmonie Club in Manhattan and the Century Country Club in Purchase, New York—two exclusive enclaves established more than one hundred years earlier by Jews who had been excluded from most other clubs in the city.

  At the same time, he quietly turned in his resignation to two all-male societies. One was the Brook Club, a clannish operation founded, according to legend, by men who were ousted from another club after they tried to poach an egg on a member’s bald head.18 Bloomberg also resigned from the militantly all-male Racquet and Tennis Club in Manhattan, a club known for refusing to allow even tennis star Evelyn David to practice on their courts in 1987.19 Denying her time in their pool, which was rumored to feature males routinely paddling around in the nude, might have made sense. But their tennis courts?