The Many Lives of Michael Bloomberg

by Eleanor Randolph

  —Bloomberg, on his decision not to run in 2020.1

  Even after becoming one of the richest people in the world, even after twelve busy years as mayor of New York City, even after making a name for himself internationally as a powerful philanthropist, Michael Bloomberg had always wanted the top American trophy. He wanted to be president of the United States. An unabashed pragmatist when it came to politics, he was prepared to switch parties to better his chances and to use his own money to sway the voters. But he was also a numbers man who knew the odds of winning the White House, and he would often joke about how his chances were slim. “What chance does a five-foot-seven billionaire Jew who’s divorced have of becoming president?” he said when his name first began to surface as a candidate.2 But the odds and his jokes never stopped him from trying. And trying. And trying.

  Bloomberg’s first real opportunity to run for the White House came in 2008 when he was still mayor of New York. A Democrat in his early years, he became a Republican in 2000 because there were too many Democrats in the race already. In 2007, he became an Independent, declaring himself to be “unaffiliated with any political party.”3 When word leaked out that he was considering a run that year as an Independent candidate, most pundits scoffed. After a hard look at the numbers, Bloomberg agreed that they were right.

  The next chance came in 2012. Although President Obama was the favorite for reelection, Bloomberg was again being mentioned as a possible candidate. (He kept saying, “No way, no how.” Publicly, at least.)4 But, facing the end of his third term as mayor and a return to relative anonymity as another rich city businessman, Bloomberg was being considered for a group called Americans Elect trying to rally support for a third-party or nonparty candidate. But as the numbers hardened against a third party, he endorsed Obama a week5 before the election.6

  Then, in 2016, Bloomberg again rallied his aides for another try. Their high-powered political operation included polls in twenty-two states. Mock television ads for his run as an Independent included one titled “All Work and No Party.” And the campaign logo (pointedly a mix of Republican red and Democratic blue, in other words, purple) was “Fix it.” Bloomberg had even vetted a potential vice president, retired former chairman of the Joint Chiefs of Staff, Michael Mullen, and the campaign staff considered the possibility of announcing an entire cabinet before the election.7

  Bloomberg’s innovative political shop churned out other possibilities. How do you get young people to the polls, for example. Their billionaire candidate could pay for a “voting app” that would call an Uber or Lyft for anyone wanting to vote (for him, they hoped).

  And what if the election were so close that it had to be decided by the House of Representatives for the first time since John Quincy Adams was elected in that manner in 1825? The Bloomberg enthusiasts harbored hopes that the then Republican House would not vote a straight party line. “We could be the non-toxic candidate,” Bradley Tusk, the seasoned Bloomberg strategist, explained.8

  Once again, Bloomberg blinked. Once again, he looked at the numbers and saw that an Independent candidate could only sway a presidential election, not win it. He would be taking away votes from Hillary Clinton. He would hand the White House to Donald Trump, and, as he put it, “That is not a risk I can take in good conscience.”9 Later, he would add a more personal reason: “My obit would be I was the guy that gave you Donald Trump. They wouldn’t have cared about anything else I had done in my life.”10

  Still, his urge to reach for the top never really went away. In the summer of 2018, rumors of a Bloomberg candidacy surfaced again, and they seemed to be confirmed in the fall when Bloomberg re-registered as a Democrat, his party until he was fifty-eight years old and first ran for mayor as a Republican. Soon he would turn seventy-seven, and in early 2019, he told his most loyal advisers, “I don’t want to have any regrets.”11 Let’s get ready, he decided. Start the engines.

  As his aides began to scramble, the field of other Democrats running for president was growing by the week. The early entrants were mostly progressives, but former vice president Joe Biden, who would later decide to run, was the clear favorite in early polls and a centrist much like Bloomberg. Biden, only a few months younger than Bloomberg, was leading with around 30 percent, while Bloomberg was near the bottom at 2 or 3 percent.12 That is not to say a Bloomberg candidacy failed to attract any support. Some observers were clearly relieved at the thought of New York’s steadier billionaire, after the tumultuous years of Donald Trump. The idea that there could be someone smart, experienced, and sane prompted New York Times columnist Frank Bruni to write, “Maybe one superrich old white guy from New York can save us from another superrich old white guy from New York.”13 BuzzFeed News offered an edgier headline that asked, “Can Mike Bloomberg Make America Boring Again?”14

  Kevin Sheekey, Howard Wolfson, Patti Harris, and the rest of the campaign team soon worked to expand their skeletal political staff into a nationwide political force. They began looking at new rules for key primaries and buying new polls. They planned trips to Florida, Michigan, and other areas where leaders were already receiving Bloomberg’s help to fight guns or climate change or receiving his grants to try new programs. Old political associates were being asked for their support—would they join Bloomberg if he ran or, if not, would they still support his alternative political effort?

  Bloomberg began to prepare his daughters, his close friends and, most important, himself for the grueling marathon. Colleagues said he was avoiding his glass or so of good wine. He went on his lettuce diet—nothing but greens until his weight got down to something a notch below slim. He purchased new contact lenses and futuristic hearing aids. And he submitted to a full checkup from his doctor in advance.

  And what did your doctor say? he was asked.

  “He said, ‘You’re gonna die.’ ” Bloomberg paused.

  “ ‘But not of anything you have now.’ ”15

  The candidate was ready. By late February, the team was ready. Bloomberg said he wanted to think, a day, maybe two. He would decide after the first weekend in March.

  * * *

  The morning of March 4, 2019, began as a bright winter day when most of New York City was preparing for a snowstorm that never came. Bloomberg called his team to the glass table near his desk on the fifth floor of his midtown offices. Sheekey and Wolfson once again outlined the possibilities and challenges. Speech writer Frank Barry was there to help craft the statement, in or out.

  Bloomberg listened to the unadorned details, the latest numbers that added up to an insurmountable roadblock for a moderate, a lonely spot in the no-man’s land of American politics. He could beat Trump one-on-one, the team figured, but the Democratic nomination?

  Fired-up progressives—many of them women—were already attacking the rich. Elizabeth Warren had proposed an “ultra millionaires’ tax” for the “tippy-top” class, a 2 percent tax on anyone with assets over $50 million that would go up to 3 percent for the nation’s five hundred or so billionaires. Bloomberg, in New Hampshire to speak at Saint Anselm College, had already declared that Warren’s plan was “probably unconstitutional,” adding, “We shouldn’t be embarrassed about our system. You want to look at a system that’s not capitalistic,“he said, adding that in one of the wealthiest countries in the world, “people are starving to death. It’s called Venezuela.”16 That same day he blasted the progressives that want “Medicare for all,” saying it was “just not practical.” And Senator Bernie Sanders’s plans for tuition-free college? Bloomberg said it was “a nice thing to do but unfortunately professors want to get paid.”17

  The centerpiece of his most recent work to combat climate change was being challenged by a group of Democrats promoting the Green New Deal. Advocated most vigorously by New York’s left-wing representative Alexandria Ocasio-Cortez of the Bronx and Queens, the Green New Deal proposed 100 percent renewable energy by 2050. The list included job guarantees and scaling back on farm emissions including “cow farts” (th
us sending opponents into a frenzy of comments about the end of hamburgers and truckloads of Gas-X needed out in cattle country).18 Bloomberg rejected the notion as “pie in the sky”19 and said that, ironically, it needed a little meat on its bones, in other words, specific goals.20

  It became clearer by the day that the new left would target Bloomberg as the Scrooge candidate despite his progressive record on such issues as climate change, same-sex marriage, gun control, and immigration reform. The path to the Democratic nomination, the only real way to combat Trump, would disappear in wasted time, energy and, not that it mattered that much, even money.

  If it was now or never, Bloomberg finally decided that morning—it was never.

  Bloomberg’s aides tried not to show their disappointment as their man stated the obvious. Now, after months of speculation and hurried preparation, there would be events to cancel, excited new staffers to deflate. If Bloomberg himself was disappointed, the stoic kept it to himself. Aides saw a man who soon seemed at peace with his decision, and instead of retiring to his Spanish and his golf swing, Bloomberg, who often counseled that the way to heal any wound was to “get over it,” seemed relieved to return to his own demon schedule. He went back to business at dawn the next day, back to London that first week for the Serpentine Gallery, where he was now chairman of the board, back to a routine that, by most accounts, was as exhilarating to him as it was exhausting to almost everybody else around him.

  In a more personal way, Mike Bloomberg was released. He no longer had to worry about what he said, not that he watched his words enough for some of those trying to protect him. There was no need to tiptoe around his fellow Democrats and the hundreds of new media outlets that beat the drums across the digital world about any misstep.

  Two weeks after Bloomberg said he was out of the running, he both shocked and entertained those at a forum in New York for the Bermuda Business Development Agency. It was a return of the brash old Bloomberg:

  “I’d already assembled a team, I was ready to go,” he began, talking about his withdrawal from the race. He mentioned his age first. If he won, he would be seventy-nine years old when he arrived at the White House.

  “And, well, people say Ronald Reagan was 80 when he left,” he continued. “Yea, when he was 80, they carried him out gaga,” to titters from the audience, many of whom were undoubtedly Reagan fans.

  “I don’t mean to exaggerate but that’s very close to being true,” Bloomberg added quickly. “To start a four-year job and maybe an eight-year job at 79 may not be the smartest thing to do,” he continued, adding that if he thought he could win, he would have run anyway. But he just didn’t see a path through the Democratic primary, he said, weaving his hands back and forth like a quarterback trying to evade a heavy defense lineup.

  “Unless”—he paused for emphasis—“I was willing to change all my views and go on what CNN called an apology tour. Joe Biden went out and apologized for being male, over 50, white.” (More titters, and, sitting on one side of him, Brian Duperreault, chief executive of American International Group, broke into an involuntary grin. Bermuda premier David Burt, seated on Bloomberg’s other side, did not seem so amused.)

  But Bloomberg hadn’t finished his screed against apologies.

  “And so everybody else, Beto, or whatever his name is, he’s apologized for being born.” Guffaws this time from the audience. “I don’t mean to be unkind, and a lot of people love him and say he’s a smart guy and someday if he wins, I would certainly support him.”21

  The untethered billionaire might offend as well as amuse, but if he was relieved, or at least released, so was his family. His daughter Emma had worked hard to stay out of the ever-expanding Bloomberg limelight. This decision could only provide more privacy for her, her husband, Chris Frissora, and their daughter, Zelda Violet Frissberg (their choice for a merged last name).

  Georgina Bloomberg, the equestrian and co-author of young fiction books, was more like her father. She immediately went on Instagram with a mock campaign photo. It showed an “I Like Mike” button attached to a placard that said, “BLOOMBERG, Because fuck this shit,” which she added was “Officially back to being just our family slogan.”22

  The high-spirited Georgina had already made her views clear in 2016 when she told a reporter that she thought her father would be “great at it,”23 but she was not looking forward to all the criticism. “When you watch the news, you can’t sit there and think, ‘Wow, I’d love one of my parents to be involved in that fight.’ ”

  * * *

  If running for president wouldn’t work, ever, Bloomberg had already moved on, as always. And if these alternative efforts succeeded, they could make him one of the most important power brokers in American politics.

  The first goal was to oust Donald Trump as president.

  “I’ve never made any secret of my belief that Donald Trump is a threat to our country,” Bloomberg said in his 2019 withdrawal statement. “It’s essential that we nominate a Democrat who will be in the strongest position to defeat Donald Trump and bring our country back together. We cannot allow the primary process to drag our party to an extreme that would diminish our chances in the general election and translate into ‘Four More Years.’ ”

  Second, Bloomberg vowed to double down on his efforts to close coal-fired power plants and fight against man-made climate change. He would also put money behind gun control resolutions around the country. He had his heart in these efforts and more and more of his money would follow. And he could back congressional candidates whose platforms included these policies—as he had done in the 2018 midterm elections.

  Third, he could shore up the Democrats, perhaps by strengthening party weaknesses in technology and fund-raising. He already had the campaign structure, and many of those who had signed on when he was deciding about a run agreed to stay on for plan B. He was also owner of a major technology empire. He and his people knew plenty about the bots, the memes, the high-energy quarters of the Internet that had become the trolling fields for Republicans and their supporters.

  By and large, Democrats proudly argued that they were on top of this advanced tech thing, or that ultimately it should not be a campaign’s top priority. Since 2016, when the Democrats were clearly outgunned, the party had taken note of their deficiencies, hired experts, and tried to catch up to the Republicans. But they were still far behind. As the party’s chief technocrat, Raffi Krikorian, admitted shortly before the midterm elections, “We are a 30-person technology team that’s charged with all the technology strategy for the Democratic Party and that’s clearly not enough to get the job done.”24 The party was no real match for Trump’s advance team that began working on the 2020 campaign four years ahead of time—fund-raising on day one as Trump was inaugurated. Republicans soon bragged about having a voter data vault, a sophisticated bank of information on almost everybody with a strong political view who ever signed on to Facebook or Instagram or Twitter or the latest new platform.25 They promised to make designer ads that fit every type, one-on-one campaign ads. The manipulation of voters had gone very high tech.

  A digital counterattack from Bloomberg might not win any Democrat the election, the Bloomberg people argued, but it could make a difference if it was as close as it was in 2016, for example, when a few thousand votes made the difference in a few key states.

  * * *

  Bloomberg’s visceral dislike of Trump and his deep concern about a Trump presidency had been on full display early in 2016. First, there was his speech at the Democratic National Convention.

  The Democrats, realizing they needed independents like Bloomberg and maybe even some Republicans, asked if he would endorse Hillary Clinton and on prime time—for 25 million people. They wouldn’t even look at the speech in advance, they promised. The slot was all his.

  Some Democrats worried that asking Bloomberg to speak was a gamble, especially for prime time. By the end of his time as mayor, he had become more relaxed in front of the microphone. He
could joke and make his points succinctly. But he could not bring the crowds to their feet like Barack Obama or Bill Clinton. He could not turn an audience into a seething mob like Donald Trump. Would Mike Bloomberg send America rushing to CSI?

  Back at the Bloomberg offices in Manhattan, the political team went to work. Frank Barry drafted the text. Howard Wolfson, who worked on the Hillary Clinton campaign in 2008 before he joined Bloomberg, eyeballed it for political traps. Others took their turn, including Kevin Sheekey and Patti Harris.

  Bloomberg then made his marks, always in pencil, a tiny script that aides complained was hard to read. Back and forth it went until the speech was complete. Then Bloomberg did something unusual. He practiced it. Twice.26

  As he showered to get ready that night, Bloomberg realized he wanted one more line. The speech had already gone out, embargoed, to a few top journalists, his staff explained. But this line was going in. No use even debating.

  In the draft as released, Bloomberg’s description of Trump already had the hard edges of a Wall Street takedown. There were plenty of good lines, polished into short bursts—a bespoke lineup for a news establishment that was madly sending out quick updates or 140-character messages on Twitter:

  “The bottom line is: he is a risky, reckless and radical choice and we can’t afford to make that choice.

  “Trump says he wants to run the nation like he runs his business. God help us.

  “I’m a New Yorker, and New Yorkers know a con when we see one.”

  Then Bloomberg added his line from the shower. “Let’s elect a sane, competent person,” he said. The implication was, of course, that Donald Trump was not merely incompetent, he was nuts.

  Trump erupted, of course. He had watched the speech and wanted to “hit” one of his critics, he said on Twitter. “I was going to hit one guy in particular, a very little guy. I was going to hit this guy so hard his head would spin. He wouldn’t know what the hell happened.” He was talking about Bloomberg,27 who is five eight (or five ten on his driver’s license), compared to Trump’s bulky six three, counting his blond pompadour. Trump claimed Bloomberg’s last term as mayor was a “disaster” and that if he ran again in New York City, he wouldn’t get 10 percent of the vote. “They would run him out of town,” he fumed.28