The Many Lives of Michael Bloomberg

by Eleanor Randolph

  Still, he was not left without a club or golf course or other high-end sanctuary. He remained a member of the Bond Club, the Century Association, the Council on Foreign Relations, the Harvard Club, the New York Yacht Club, the Kappa Beta Phi fraternity, the Golf Club of Purchase, New York, a favorite of Wall Street types,20 the Caves Valley Golf Club, a course for serious golfers near Washington, D.C., and, in Bermuda, his weekend getaway of choice, the Coral Beach & Tennis Club, and the Mid Ocean Club.21 He sold his half of a billionaire’s requisite yacht, an admission of excess that Bill Cunningham, a top campaign adviser, insisted was not a big deal. “It’s not an aircraft carrier. It’s not a submarine,” he said. “It’s just a boat.”22

  Bloomberg’s problems with women at his company hovered as a potential hazard, but news accounts of the harassment charges by female employees and the vehement denials by Bloomberg came early—even before he had announced. Did his campaign leak the news in order to inoculate the candidate? The answer is almost certainly yes, as author Chris McNickle wrote in 2017.23 That’s the standard campaign way to downplay a bit of bad personal history—get it out early.

  Ten weeks before Bloomberg announced, the New York Daily News had trumpeted the women’s accusations, the lawsuits, the accusations of things Bloomberg allegedly said (like “Kill it” to a pregnant worker), and the vehement denials by Bloomberg.24 Political regulars chuckled privately as a nonpolitician tried to air out his past before he went public. An aide to Peter Vallone, said that the ruckus in the tabloids “reinforces the fact that Bloomberg is not a serious threat, and his candidacy isn’t quite ready for prime time.”25

  Far from being disheartened, Bloomberg’s advisers saw the muted response and believed they had won a pass. If reporters brought it up later, the campaign could point out that Bloomberg had already denied it and passed a lie detector test. The cases were settled, and it would be old news.26

  Undaunted, or more characteristically even encouraged by the naysayers, Bloomberg finally declared his candidacy on June 5, 2001. His speech announcing his run for city hall was three and a half pages long and used the pronoun “I” 117 times, as columnist Gail Collins noted in the Times.27 No matter. The actual announcement, the real introduction to city voters, was on television, the beginnings of a televised blitz that would be part of a campaign that would eventually cost Bloomberg a stunning $74 million.

  As Bloomberg began his first run for public office, surveys for the Quinnipiac University Poll showed him more than thirty points down, just one step over invisible.28 Most Republicans didn’t think he had a chance, but Bloomberg, who once estimated that he would not spend more than $30 million to get elected, was now ready to fork over whatever it took to get the nomination. As one writer put it, the GOP “welcomed Bloomberg with open pockets.”29

  Soon, even then governor George Pataki ditched Badillo and endorsed Bloomberg. At their first joint press conference, Pataki was standing next to the freshly initiated Republican when a reporter asked the billionaire candidate if he was really, truly a Republican, given that he seemed to be awfully liberal. “I AM a liberal,” Bloomberg answered as Pataki flinched. And after several more questions like those about his liberal views on guns, abortion, and gay rights, Bloomberg grinned and made himself perfectly clear: “I’m a liberal. I’m a liberal. I’m a liberal. I’m a LIBERAL,” he said. Pataki remembered working hard to keep a smile on his face. This was not on the talking points memo, but, as the governor would soon learn, it was standard “I am what I am” Bloomberg.30

  The business community rallied, of course. But others did not fall in line so easily. Betsy Gotbaum, a high-energy force around the city, had been a parks commissioner under Mayor Dinkins and president of the New-York Historical Society, saving it from a dusty bankruptcy and the loss of a splendid building on Central Park West. Bloomberg supported the society and had become a social friend.

  So Bloomberg assumed Gotbaum was on board. Not so fast, she explained. A lifelong Democrat whose husband, Victor, had been a prominent labor leader, she was running for the job of public advocate, the city’s ombudsman. Endorsing a Republican or criticizing Bloomberg’s opponent would be political treason in her world, even for a friend. Bloomberg, however, saw her political attachment as a form of desertion.

  When they both won, Gotbaum expected an easy relationship with the mayor, not like the daily spats between former public advocate Mark Green and ex-mayor Rudy Giuliani. That wasn’t going to happen, she was shocked to learn. She had been disloyal, she was told, and he would have no trouble cutting her budget and getting city voters to drastically limit the public advocate’s position, in other words, her job. It was a very public war. But when her husband died nearly a year and a half after the mayor left office, Gotbaum said that the first outsider to call and offer his sympathy was Mike Bloomberg.31

  If Bloomberg had plenty of money to run for office, a successful candidate also needs something even Mike Bloomberg could not buy—pure, old-fashioned luck. In 2001, this political newbie enjoyed three unexpected advantages, the most important being the disaster on September 11 that alarmed the city and rattled its voters.

  But there were also other circumstances that favored this political novice. First, nobody thought he could win, including himself. A few months before he announced, Bloomberg told Israel’s prime minister, Ariel Sharon: “Am I running? Probably. Will I win? Not a chance.”32 So he made a lot of his mistakes (and gave a lot of really terrible speeches) early, while nobody was really looking. The press and the political diggers from the opposition mostly gave him a pass—until it was too late.

  “If you go back to when he first announced that he was running, people were cracking jokes. He was just kind of goofy,” recalled Joe DePlasco, who ran the campaign of his main opponent, Democrat Mark Green.

  “I remember [a Times reporter] calling after the election and saying, you know, he was sorry that they did not give Bloomberg a bigger and deeper look,” he said. “All that stuff you would have investigated—the background, the expenditures on political stuff, business decisions, personality flaws, whatever, that didn’t take place,” he groused. “They didn’t have the immediate scrutiny that you would have normally in an election.”33

  The second bit of good fortune for Bloomberg was that his Democratic opponent was Mark Green. Green, who had been a steady and sometimes strident voice for reform as the city’s public advocate, was an arrogant and abrasive man. He had a talent for offending people, even if they agreed with every single word he said. Green managed to divide the Democrats, offend key unions, alienate blacks and Hispanics, and generally drive a sure win by the Democrats that year into a humiliating loss.

  Still, the most fateful event for that election and for America in the years ahead was the terrorist attack on the World Trade Center towers on September 11, 2001. With what would become 2,76334 city deaths and the catastrophic destruction of the massive Twin Towers, even tough New Yorkers were shaken. Suddenly, enough city residents would yearn for stability, and Mike Bloomberg’s wooden but dependable candidacy fit the needs of that moment. Bloomberg looked like a successful manager, a qualified chairman at city hall, a steady hand that could control the budget, supervise the city’s 300,000 workers, and generally reign as a paternal figure who could take care of the city’s eight million residents.

  Some voters went to the polls four times that fall. The city primary on September 11 was quickly canceled. There were even people who said the election saved their lives because they stood in the polling place waiting to vote before going to work at or near the World Trade Center. Most New Yorkers could tell you exactly what they did that day, how they watched the destruction on TV or, in real time, who they called, where they were. Bloomberg was in his campaign office, eye on the television, phone at his ear. Voting for mayor was not a priority that day, even for him.

  A new primary was set for September 25, and Bloomberg easily bested his Republican opponent with 72.3 percent of the vote, even
though Badillo had tried, and failed, to make an issue of Bloomberg’s money and the lawsuits from women in his company. Most people, including most of the media, were watching the Democrats, where Green was forced into a runoff with Fernando Ferrer because neither candidate won 40 percent of the vote. Green, who eventually clawed his way to a win against Ferrer, was so confident he could beat Bloomberg that he had already begun offering jobs in his future administration. He repeatedly scoffed at the idea of Bloomberg as mayor, at one point calling Bloomberg’s plan to add schools on Governors Island off the Manhattan shoreline “the naivete of a novice.” “I don’t think he knows the city, and I don’t think he understands government,” Green sneered. “When he’s been to all the neighborhoods like I have, perhaps he’ll be slightly more insightful and credible.”35

  Although his opponents and the press had mostly failed to notice, Bloomberg had been going to all those neighborhoods. He had been steadily meeting people in every borough and finding, to his relief, that all sorts of New Yorkers felt comfortable with his stiff but genuine salesmanship. When he worked to make people like him, they liked him. He was indeed odd, even for a billionaire. He droned through his speeches, like a schoolkid reading a book report, and he had this strange way of speaking—part Massachusetts, part Bloomberg. The word “anyway” always turned into “anyways.” But, hey, he wasn’t fake, New Yorkers figured.

  While Bloomberg was shaking hands and promising a better city, his campaign staff was working just as hard trying to introduce this very rich white man to a very diverse city. Jonathan Capehart, who had been a Bloomberg reporter before he began working to help Bloomberg connect with the African American community, tried to get his subject to loosen up, especially when he visited the city’s powerful black churches. Capehart explained to the candidate that religion in a black church is physical. The organ thumps and the choir soars and people clap and stomp their feet and sing and sway to worship joyously with their whole bodies.

  Bloomberg would just stand there, once in the same church as Green, who tried to rock along with the congregation. Capehart remembered asking him, “Mike, you know, it’s church. You can’t clap? You can’t move? He said, ‘Hey, listen, I could try to pander and pretend like I know what to do and that this is part of my tradition or I’ve been around this all my life, but I haven’t. And it’s not part of my tradition so I’m not going to pretend to be someone I’m not.’ ”

  Capehart added, “I thought, you know what, good for him. There’s nothing more terrible than to see a politician, and particularly a white politician, trying to get down in a black church when they’ve never done it before.”36

  To reporters covering his campaign, this stiff candidate seemed odd for a man who had a reputation straight out of the high energy and low morality of Wall Street. To some, it became clear that he was trying hard, sometimes painfully hard, to stop from blurting out what he might have said on the Salomon Brothers trading floor. Still, he could occasionally go off script and offer a few glimpses of the inner Bloomberg.

  In a key economic address at a breakfast given by Crain’s business magazine in October 2001, he began advising executives from the city’s top corporations to avoid hiring people from the suburbs. They are not “the best and the brightest,” he explained. “This is a self-selection process. People who want to go there [Connecticut or Westchester, for example] aren’t the people that you want to have in your company.”37 It might have hurt him with his richer suburban friends, but it sounded right to New Yorkers. Whether he understood that it might be helping him with the voters, it wasn’t planned, wasn’t in the text. It was just what he wanted to say at the moment.

  During one early interview, Bloomberg was asked what had become a standard question for politicians—had he ever smoked marijuana? Bloomberg said, “You bet I did. And I enjoyed it.” A national pro-marijuana campaign later used the quote as part of an ad that showed a very bleary-eyed Bloomberg with the line: “At last, an Honest Politician.” (Bloomberg would later admit that although he regretted the remark, it “was the truth.” And he would later oppose decriminalization of the drug, especially in his city.)38

  At another point early in 2001, he was talking about how students could apply for jobs. He said that too often students from the city’s public schools “don’t know how to present themselves. They have personal hygiene problems. These are the things that drive employers crazy.”39

  As Bloomberg’s poll numbers went up, the state Democratic chair, Judith Hope, put out a list of Bloomberg’s “offensive remarks” and “blunders.” They included items from the Bloomberg birthday book of quotes compiled in part by a former Bloomberg employee, Elisabeth DeMarse, for Bloomberg’s fiftieth birthday. After DeMarse admitted she had released the book and some of the quotes were printed in New York magazine in September,40 she got a call from a Bloomberg lawyer suggesting, as she put it, that “they were going to take all my money” because she had broken her confidentiality agreement with the company.

  “I didn’t worry,” DeMarse laughed years later. “At that point, I didn’t have any money.”41

  As Bloomberg made headway in private polls, the Democrats pulled out those old jokes and tried to make them sound like campaign statements by the Republican candidate. Their list included:

  “I make it a rule never to go to Queens, and since that eliminates both airports, I don’t travel very much.”

  “The three biggest lies are: The check’s in the mail. I’ll respect you in the morning, and I’m glad that I’m Jewish.”

  Hope wrote that “New Yorkers deserve to know about the offensive things their Republican candidate for Mayor has said about women, the borough of Queens and being Jewish.”

  There was, of course, no suggestion by the opposition that these might have been jokes, even terribly old ones. Bloomberg labeled them old “Borscht belt” standbys.42

  Not funny, the joyless Green campaign argued. Green tried desperately to add these quotes as an antidote to the television ads and expensive flyers stuffed in mailboxes of potential voters. These Bloomberg ads showed a strong-looking guy who described himself as “a self-made man from a working-class family.” Television commercials hammered the idea of a competent businessman who had an impish grin and who exuded the kind of confidence of a man who was in control of the world around him. Many voters could see through Green’s umbrage and once again registered Bloomberg’s “blunders” as a little crude authenticity not unknown in the big city.

  The real issue, Green and other Democrats said, was his money. How could people tolerate a rich man buying his way into office? the Green campaign asked. Bloomberg and his campaign turned the question on its head, arguing that it was so much better for him to pay his own bills than to take money from some leftover Tammany Hall wannabe who would ask for favors if he won. (He would later help the city pass a law limiting contributions to candidates from companies that do business with the city. That law would eventually impose a $25,000 fine for taking donations from those on the “doing business database”.)43

  In the end, the New York Times editorials, which had supported the Republican Giuliani in 1997, backed the Democratic candidate Green and argued that Bloomberg’s money was indeed the main issue in the campaign.44 New York City had a model system of public financing for political campaigns that parceled out matching funds to candidates who participated, followed the rules, and ran legitimate races. The system encouraged competition, and it was supposed to provide a hedge against rich candidates like Bloomberg. The problem was that even New York City’s campaign budget could not offer much protection from nearly $74 million. Bloomberg, of course, did not participate in the system.

  * * *

  As the campaign took off, Stu Loeser, Mark Green’s prime researcher, put together a package he called the “Bloomberg White Paper,” designed to reveal the underreported flaws of their billionaire opponent. The Loeser team criticized the Bloomberg company’s treatment of workers who made his keyboards
in Mexico and accused him of running his company like “an electronic sweatshop”45 with hours rivaling the Salvadorean sweatshops that, incidentally, made his campaign T-shirts. (Bloomberg canceled the T-shirt contract shortly after he was asked about the treatment of those workers.) The candidate had indulged in what the Green investigators called “abusive/boorish behavior” about women, and the man who made his money in the world of computers had said repeatedly that classrooms should not have computers for the youngest students. (He wanted children to focus on books and the blackboard and the teacher, not on individual machines—an idea which drew jeers from the Green camp.)

  DePlasco and Loeser tried to peddle the details not mentioned in Bloomberg’s smooth television ads, but Bloomberg’s flaws barely made the news. And in the end Loeser didn’t find enough to sour on his target. In 2005 he joined the Bloomberg political team, and in 2006 he became Bloomberg’s press secretary in city hall.46

  The 2001 campaign reached its peak in mid-October, even though most New Yorkers were focused elsewhere after 9/11. Each day seemed to bring the painful sound of bagpipes keening “Amazing Grace” in memory of another firefighter or police officer lost at the World Trade Center. The media was full of alarming new warnings about anonymous letters containing powder—some of it lethal anthrax, some of it talcum powder sent more to harass than to harm. A journalist in Florida died after opening a letter seeded with anthrax spores. Two assistants to NBC anchor Tom Brokaw grew violently ill after dealing with his mail—a “letter that looked as if it were written by a child.”47 Mail rooms around New York City were on alert, watching for strange packages or envelopes, and some mail clerks had to have hazmat suits ready if a suspicious letter appeared. The economy, already showing signs of weakness before 9/11, was slipping dramatically in New York, as tourists canceled Christmas vacations in the newly damaged city. New York was sliding into hard times.48