The Many Lives of Michael Bloomberg

by Eleanor Randolph

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  CONTENTS

  Introduction

  1. BORN TO RUN, EVERYTHING

  2. THE WAY UP

  3. THE SALOMON BROTHERHOOD

  4. THE MAKING OF A BLOOMBERG

  5. BLOOMBERG MAKES THE NEWS

  6. LIFE IN THE BLOOMBERG FISHBOWL

  7. THE BLOOMBERG WOMEN

  8. RUNNING ON MONEY

  9. FIRST HUNDRED DAYS

  10. A BILLIONAIRE’S CITY HALL

  11. A LABORATORY FOR URBAN REFORM

  12. THE “NANNY” MAYOR

  13. THE GEEK SQUAD

  14. THAT PUBLIC SCHOOL BUSINESS

  15. OFF HOURS

  16. BLOOMBERG’S BULLDOG

  17. THE FORGOTTEN ISLAND

  18. THE CITY GROWS UP AND UP

  19. TAKING THE HIGH LINE

  20. FROM LOW POINT TO LANDSLIDE—2005

  21. A CITY ON THE MOVE

  22. SILICON ISLAND

  23. AS FOR THE OTHER HALF

  24. OVERTIME

  25. BACK TO BUSINESS

  26. MOVING TARGETS NOT SITTING DUCKS

  27. GIVING BACK

  28. GREEN FOR GREEN

  29. GOVERNMENT IN EXILE

  Photographs

  Acknowledgments

  About the Author

  Note on Sources

  Notes

  Bibliography

  Index

  Photo Credits

  For Peter and Victoria

  INTRODUCTION

  THE MANY LIVES OF MICHAEL BLOOMBERG

  “I don’t have anything in common with people who stand on escalators. I always walk up them—why waste time? You have eternity to rest when you die.”

  —Michael Bloomberg, 20141

  When billionaire Michael Bloomberg announced that he was running for mayor of New York in June 2001, the city’s pundits scoffed. “Kinda goofy,” said one.2 Another predicted, “There is no turn of events at all, no leap of logic whatsoever, that could make Michael Bloomberg New York’s next mayor . . .”3 Sure, he could overwhelm the city’s airwaves and mailboxes with expensive commercials, they noted, and voters could be reminded that he was a generous donor to city charities big and small. But this was a vanity project, the experts decided, another rich man’s expensive hobby.

  Yet, these doubters were soon confounded by two important realities. First, they had underestimated how a driven Michael Bloomberg would use his energy and his money to achieve his latest goal. They had misjudged him as a tin-eared and boring novice, and they had missed the complex and relentlessly ambitious salesman underneath. As Bloomberg emerged as the billionaire candidate that year, he was not sitting on a yacht somewhere, offering his latest political whims by long distance. He was out there shaking hands and freely granting interviews, studying polls, and giving some of the worst political speeches New Yorkers had heard in years. No matter. He was out there, learning how to be a big-city politician, starting at the top.

  Then came the morning of September 11 when New York endured the deadliest attack on American soil since Pearl Harbor. Nearly three thousand people died, a whole swath of Lower Manhattan was destroyed, and the nation’s largest city faced the possibility of economic and spiritual decline. Voters began looking for someone who could put the city back together. Bloomberg’s campaign literature sold him as “a leader, not a politician,” a man who tried to fix problems, not simply complain about them.

  When he won, some suggested it was not just his billions, it was a dark form of luck. But, as E. B. White so famously noted, “No one should come to New York to live unless he is willing to be lucky,” and Bloomberg was indeed a lucky man. He had started his business at the right time and had run for mayor at the right moment. (An aide once insisted that he led such a charmed life that when he bet on a horse with the longest odds, he ended up stuffing his pocket with winnings he didn’t need.) Still, Bloomberg was prepared to work extra hard, to use any turn of events to his advantage. He would not only become one of New York City’s most inventive and productive mayors, but he would also become a modern American phenomenon, using his money and his clout in an attempt to improve the lives of millions of people and to preserve the planet where they live.

  * * *

  By 2019, Michael Rubens Bloomberg had come a long way from his modest, working-class roots in Massachusetts. If most people have one career per lifetime, this man had already managed three. He had created a computer product that upended the old guard on Wall Street and made him one of the richest men in the world. Then he had served as mayor of New York City for twelve busy years. After that, he had taken his billions to become one of the world’s most inventive philanthropists, pledging to give away his fortune, or most of it, before he died.

  As the 2020 presidential election loomed, Mike Bloomberg was clearly eyeing a fourth mission, this time to challenge a president he viewed as a con man and a threat to America. If he would not be a candidate for president—and that had always looked tantalizing but impossible—he would be a political sugar daddy and guru for the often disoriented and underfunded Democratic Party. He would not be idle—that, he promised.

  This book is an attempt to chronicle the many lives of a man who chafes at an empty hour on his calendar. He can sit rock-hard-still and listen with a searing intensity when people come to him with proposals for his business or his politics or his philanthropy. (The Bloomberg fidget is never a good sign for anyone asking for his approval.) But mostly this perpetually ambitious man moves and adapts with incredible energy from one pursuit to another to another. He does not rest very long on his successes or brood about past failures. And when something goes haywire or simply ends (like his time at city hall), his first question is often a simple one: What’s plan B?

  * * *

  Bloomberg started his adult life on Wall Street. With an engineering degree from Johns Hopkins and extra glister from Harvard Business School, he first learned about the raw, greedy world of stocks, bonds, and big money at Salomon Brothers, a top brokerage in his day. In the late 1960s and 1970s, Bloomberg could fit into the raucous screw-you culture, but he was also different. Unlike many of his elders, the young Bloomberg foresaw the day when computers would eliminate the mountains of paper required to do business. He began to propose a computer system for Wall Street, and the old boys laughed at him. They demoted him to the computer floor and then fired him in 1981 with a generous payout of $10 million.

  Bloomberg and three young Salomon techies quickly started a new business. Those beginnings are now the stuff of Bloomberg lore, and he will often say those were the happiest times as a boss—when he knew everybody who worked for him and could hand out paychecks one by one. Bloomberg’s computer gizmo began working for bond traders before the Internet had taken hold, and as computers became the gateway and the impetus for a far more complex financial world, his business and his wealth grew astronomically. Career one would provide the funds for his other ventures over the next four decades.

  Then came politics. In the late 1990s, after fifteen years as an inventive businessman, Bloomberg told friends he was ready for something new. One associate thought he wanted to become the U.S. ambassador to the United Kingdom. Others saw him eyeing what most peo
ple thought was impossible; he wanted to manage the biggest city in America.

  In many ways, what made Bloomberg different from his billionaire class was that decision to emerge from his wealth-protected cocoon to face press and public as mayor of New York City. After twelve years and at least $650 million of his own money (nearly half of it spent on his campaigns), the Bloomberg era can now be seen as a testing ground for how a modern businessman could manage a very complicated city. It will undoubtedly attract years of study by academics and urban experts about what worked and what didn’t during his busy time as mayor. He would fail in important ways, often involving the city’s poor. Too many black and Hispanic youths were stopped and frisked in the name of gun control. Homeless rates soared and public housing suffered. But he improved much of the city, especially the health of its people and the effectiveness of its government. Overall, his time as mayor was a remarkable success.

  The third Michael Bloomberg has been a giver, a philanthropist, fighting what he called public health issues that included battles against tobacco, guns, obesity, traffic deaths, and above all the man-made climate changes disrupting the entire planet. He had learned from his time in the city to trust in the power of good mayors. He had seen their problems up close, and he gave millions to cities, arguing that mayors could often solve problems better than distant bureaucrats or politicians. In 2018, he was the second most generous billionaire in America (after the richest man in the world, Jeff Bezos), and by 2019 Bloomberg’s staff had calculated that he had given away almost $10 billion so far at age seventy-seven. That left another $45 billion or more to go.

  The fourth Bloomberg was the manager who kept hoping he could manage the entire country. In 2019, alarmed at how President Donald Trump was dismantling so many of the protections Americans had enjoyed and damaging the world’s environment, Bloomberg at first began marching through the stations of America’s presidential primaries—Iowa, New Hampshire, Florida. But, just as he had done three times before, Bloomberg decided that he simply couldn’t prevail in the long trek to the White House. Instead, he would spend his time and especially his money on the main goal for 2020—ousting President Donald Trump.

  Once again, Bloomberg had a new challenge. If he could not survive as the candidate, he could be the very rich, very savvy techno-mensch that the Democratic Party needed. And he would support those candidates who agreed with his policies, as he had done with some success in the midterms in 2018. He would spend $500 million to fight climate changes and coal-fired power plants. And after that? He once said, with a smile, of course, that he planned to live to 125 (his mother died at 102, and he has the best medical care and advice money can buy). If so, that certainly leaves time for still another version of Michael Bloomberg.

  * * *

  More than a few of Bloomberg’s admirers warned that it made no sense to look for a deep, psychological road map to this intense character. He had a stable childhood, tough and loving parents. He was an Eagle Scout. He survived at Johns Hopkins, Harvard. He married a British beauty and kept her as a friend after they divorced. He doted on his two daughters and, as of this writing, his two grandchildren. He was extremely proud to be Jewish, but not overly religious. He was not a philosopher, not an intellectual. (He once claimed his favorite book was a John le Carré novel and his favorite movie was Mel Brooks’s Blazing Saddles.) Instead, he was a brainy engineer who has always wanted to improve things and make them run better, from a squeaky door to notoriously messy things like city government. He was a doer, “Mr. Fixit,” some of his colleagues liked to call him. But he also wanted things done and fixed quickly, as quickly as humanly possible. Asked about how he saw his role in all these careers, he said, “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. Some good. Some bad, but that’s what I do.”4

  As he became a more public figure, the younger version, the Wall Street, smart-ass Bloomberg, remained mostly tucked under the standard businessman’s blue serge regalia. From outside, he was distant, flat, stoic, grumpy to the press and, of course, stilted at the microphone. His face, often set in an inscrutable grin, seemed halfway between the Grinch and the flirt. It could be his distant look or his mischievous look. One colleague called it his “twinkle,” a semi-smile that seemed to hint at some risky pleasure.

  He was a masterful salesman who packed a variety of Michael Bloombergs into his bantam five-eight frame. He could fraternize in the morning with the muscular “Sandhogs” digging a water tunnel under New York City’s streets, and by evening he could be at a gala, blowing air-kisses at the frosty Anna Wintour, editor of Vogue. He could be funny and privately raunchy with a full repertoire of old Catskill jokes that were sometimes edgy and sometimes slipped over that edge.

  His comments about women, leftovers from his feral Wall Street days, would get him into trouble, even as he denied making them. The response from Bloomberg and his people was that women thrived at his company and that he had been surrounded by strong women all his life, starting with his powerful mother and in later years, his top adviser and confidante, Patti Harris.

  Like a lot of men of his era, he showed signs of discomfort that old behaviors were being judged by strict new standards. At one point, he said he had canceled plans to run for president in 2020 because he would not “change all my views and go on what CNN called an apology tour.” He added, “Joe Biden went out and apologized for being male, over 50, white.”5

  Michael “Call me Mike” Bloomberg enjoyed a full plate of contradictions. One example: he wanted all his employees to sit around him, to be available and nearby, to be within earshot. Privacy was a luxury in that office-free world, but for Bloomberg, at least, the bull pen always had its escape hatch. Although he pestered his staff by phone or email on evenings and weekends, those private hours were supposed to be completely off the record. While he was mayor, a Times reporter nosed around his well-guarded compound in Bermuda. Bloomberg was furious. His aides let it be known that he was a public figure only when he chose to be public. The press, of course, begged to differ.

  That same man who craved his privacy also relished the spotlight. Dan Doctoroff, who was a deputy mayor and then the head of Bloomberg’s company, described the mayor as being “incredibly anxious” about losing the limelight and the microphone once he left office. Doctoroff said he scoffed at the very idea and told Bloomberg, “You’re going to be at the center of whatever you want to be for the rest of your life!”6

  There was also something of a cowboy inside that expensive suit. Against all sorts of advice from friends and aides, he took on one of the toughest hombres in politics—the National Rifle Association. His anti-gun campaign would help break the NRA’s chokehold on politicians who were often terrified to even mention gun control in the face of rising gun deaths in America. It was a campaign that began when he was mayor and grew more intense after he left office.

  But if that was a little too theoretical, Bloomberg had also been known to confront the bad guys, face-to-face. When two hackers from Kazakhstan found a way into the Bloomberg LP computers, learning details about Bloomberg’s own passwords and credit card accounts, Bloomberg began working with the FBI. Soon he agreed to meet the intruders in a London hotel as part of an “exchange” of money for information about the attack. As he walked out of the room that day, agents walked in. They arrested the two, who were soon extradited to the U.S., and one was convicted; the other deported.7 Asked years later why he wasn’t afraid of being alone in a hotel room with two people from the wild reaches of Kazakhstan, men intent on robbing him or worse, Bloomberg shrugged and said, with his all-purpose grin, “I don’t do fear well.”8

  Almost everybody who talked about working closely with Bloomberg mentioned his view of loyalty. If you were loyal to him, he would be loyal to you, they said, almost as a mantra. And anyone who resigned from his company to work elsewhere was never to be hired again. There could be no going-aw
ay parties for someone who had committed his version of corporate treason.

  Loyalty would also make a dent in his reputation, however, especially when his police commissioner, Ray Kelly, oversaw a department that stopped, frisked, and too often humiliated hundreds of thousands of blacks and Hispanics in the search for illegal guns. Even after the Kelly version was ruled unconstitutional, Bloomberg would continue to publicly support his police commissioner’s efforts—as his attempt to stop shootings, to stop young blacks and Hispanics in higher-crime areas from killing one another.

  For all his concern about fighting big problems, Bloomberg could also tackle the less serious ones with much the same fervor. One spring, he and Governor Andrew Cuomo competed in what was supposed to be a promotional white-water rafting contest in the Adirondacks. The two teams battled through the rapids in upstate New York, and afterward, the timekeeper announced the governor’s team beat the mayor’s team by eighteen seconds. Cuomo said Bloomberg complained repeatedly that he felt robbed, especially since the timekeeper worked for the governor. Weeks later, one member of Bloomberg’s white-water squad asked him to sign a photo showing the mayor and his paddlers madly churning through the rapids. Bloomberg grinned, took the photo, and wrote: “18 seconds, my ass.”9

  * * *

  The flat, conventional view of Mike Bloomberg was always missing more than a few more dimensions. He was a natural manager who could give employees plenty of freedom, money, and support but could fire an aide caught playing computer solitaire during working hours. For almost any project, he could gather a group of terrified aides who knew he would ask the hardest questions or redraw their graph or demand better data and a clearer version of whatever they were trying to say. He could be stubborn and cold, refusing to give up some personal pleasure like a golf game when he was needed at a city event. But he also could be generous and thoughtful, calling widows of city workers killed while he was mayor as he left office. He was notoriously impatient, a good thing in government. And he was extraordinarily self-disciplined—adding extra work hours to his schedule or reverting to his “lettuce” diet when his weight hit an uncomfortable number.