By The Washington Post · Sarah Ellison, Roxanne Roberts
But his billionaire lifestyle lifted off at helipads around the city, and he sometimes used one on the East River at 34th Street, where Bloomberg piloted his own helicopter out of Manhattan during hours the city declared off-limits.
Irked by the din of the helicopter engine and the odor of its fuel, a disgruntled neighbor recorded Bloomberg's comings and goings in 2012 and gave the video to a local ABC news station.
The New York press corps pounced. When asked about the illicit weekend travel, Bloomberg said he would no longer use that particular helipad, but his irritation was clear: "Don't know why it's such a big deal," he told reporters. "If that's the news that's fit to print in this day and age, it's a sad day."
Bloomberg's wealth is the defining feature of his presidential bid, a massive asset and political target. He had an estimated net worth of $60.5 billion as of Jan. 29, according to Forbes, making him the ninth-richest person in the world and the wealthiest by far to seek the Oval Office. He's richer than the poorest 125 million Americans combined, a fact Bernie Sanders calls "wrong" and "immoral."
If the 2020 election is a referendum on how Americans feel about money, Bloomberg is either the ultimate expression of the American Dream or one symbol of a corrupt system. In either case, the way he spends his money is one clue as to the kind of president he would be.
"I can't speak for all billionaires," he said during a recent debate. "All I know is, I've been very lucky, made a lot of money, and I'm giving it all away to make this country better."
He's gifted $10 billion to various philanthropic causes. Apart from that, he's poured more than $500 million into the presidential race this year. Campaign advisers say Bloomberg will spend "whatever it takes" to defeat President Donald Trump - whoever is the Democratic nominee. At his current spend rate, that could cost him $2 billion or more.
But he hasn't given it all away.
Over the past 30 years, he's acquired lavish homes, private jets and a modern-art collection - the life of the One Percent of the One Percent. But the money itself was never the point, according to interviews with Bloomberg's friends and biographers. They say he uses his fortune to shape the world to his vision.
Rewind the clock to 1981. That year Bloomberg was forced out of his job as a millionaire partner at the Wall Street firm Salomon Brothers. It was a blow, but softened by a $10 million severance package. On his last day of work, he gave his wife of five years a sable jacket.
"I was worried that Sue might be ashamed of my new, less visible status and concerned I couldn't support the family," he wrote in his 1997 autobiography "Bloomberg by Bloomberg." "A sable jacket seemed to say, 'No sweat. We can still eat. We're still players.'"
But in the political realm, his assets were sometimes a liability - and a blind spot. As mayor, he spent many weekends golfing in Bermuda and refused to release his schedule to the media while he was there.
During a devastating blizzard in 2010, his administration's slow response crippled many snowbound New Yorkers. Bloomberg, who rushed back from the island for the storm, initially dismissed the impact on residents. "The city is going fine," he told reporters. To prove his point: "Broadway shows were full last night."
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Bloomberg was 39 years old when he used $4 million of his severance to create the Bloomberg Terminal, a device that gave financial institutions instantaneous analytics. "Nobody in 40 years has come up with anything comparable to what Mike has," says David Rubenstein, a fellow billionaire and philanthropist.
According to Forbes, Bloomberg currently owns a staggering 88 percent of the privately held business, which had an estimated annual revenue of $10 billion in 2018.
He was and remains an unabashed capitalist, proud of what he built and the country that allowed it to happen. Like most self-made men, he attributes it all to hard work.
The life story the campaign tells about Bloomberg is of a childhood spent in a working-class suburb of Boston, and an education at Johns Hopkins University and Harvard Business School funded by student loans, followed by 15 years on Wall Street. All that all before he had his entrepreneurial idea.
It took Bloomberg, who declined to comment for this story, five years after he founded his own company to make his first major purchase, spending $3.5 million on a townhouse at 17 East 79th Street, steps from Central Park. It was a statement to the world that he'd made it, and it remains his primary residence. The property is now worth at least 10 times the purchase price.
The five-story Beaux-Arts limestone property started with 7,500 square feet. But Bloomberg purchased five of the six apartments in the building next door. He knocked down walls to accommodate his frequent dinner parties, where he presides as an elegant host while serving fried chicken and coleslaw. ("Pretentious in their unpretentiousness." described New York magazine in 2005.)
Local reporters knew Bloomberg and his longtime partner, Diana Taylor, were A-list clients of decorator Jamie Drake. (The then-mayor chose Drake to redo Gracie Mansion, although he never moved in.) But when the designer posted Bloomberg's Manhattan and London antique-filled townhouses on his website without identifying the owner, the media got their first look: Old Masters paintings, a $1 million Georgian Chippendale couch, an antique snooker table, and the faux-leopard upholstery. It was opulent, tasteful and a little over the top.
"Michael wants to live large, like a 19th century railroad baron," then Vanity Fair editor Graydon Carter told the New York Times in 2001. "He sees himself as very much like the Carnegies or Mellons." And New York A-listers saw him that way, too. Bloomberg was respected and embraced by the moneyed society of New York - unlike Trump, who was dismissed as a nouveau riche tabloid mainstay.
In 2006, Bloomberg chose to locate his primary foundation, Bloomberg Philanthropies, around the corner from his home in two combined buildings worth an estimated $86 million, according to property records. There's a condo on Park Avenue, three properties in upstate New York and a condo in Vail, according to financial disclosures he filed as mayor. His Ballyshear Estate, a 1913 oceanside mansion in Southampton, sits on 35 acres with a garden designed by Frederick Law Olmsted, who also created Central Park.
At least half of the properties aren't for his personal use and are primarily for his family members, including his two daughters, Emma and Georgina, and his grandchildren, according to his campaign.
Overseas, the self-professed Anglophile has two homes in London, where he stays when visiting Bloomberg LP's sizable office in the city: A three-story Victorian on Cadogan Square and an townhouse in Chelsea where author George Eliot once lived. The Cadogan Square property features sweeping staircases, marble columns and paintings by American artists such as Jasper Johns and Andy Warhol. Bloomberg, who calls London his second home, has an active social life in the city and is chairman of the board of trustees for the Serpentine Galleries.
Then there's the controversial home in Bermuda. He purchased a modest seaside estate in 1998 and replaced it with a $10 million, 6,000 square-foot retreat, with neighbors such as the late businessman Ross Perot and Silvio Berlusconi, the former prime minister of Italy. Bermuda is his favorite place to play golf, which he took up later in life and has obsessively attempted to conquer.
He also owns private jets - notably a Dassault Falcon 900B - and an Agusta SPA A1095 helicopter handpicked by Bloomberg.
"One of his friends said that he saw money as a ticket to the rest of the world," says Eleanor Randolph, author of "The Many Lives of Michael Bloomberg." "Not so much things he could buy, but as a source of power."
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"Philanthropy and public service are my two great loves after my daughters and my company," he wrote in 1997, a year after he wrote his first multimillion-dollar check to Johns Hopkins University. "There are few people as lucky as I have been. Depending on your perspective, I deserve it or I don't. No matter which, I have it."
As a trustee of the university, Bloomberg became taken with the idea of using wealth to save lives. He's given a total of $3.3 billion to his alma mater, the largest single recipient of his philanthropy.
"I never have met anyone in any profession that got the idea so quickly," said Al Sommer, then-dean of the university's School of Public Health. Bloomberg is now one of the most generous philanthropists in America, promoting gun safety, environmental protection, education, women's rights and health care.
But Bloomberg has said he believes private philanthropy can do only so much. In 2001, when he was 59 years old, he decided to run for mayor.
During that first campaign, reporters questioned the billionaire about why he hadn't released his tax returns. Bloomberg chafed at the request, as if his considerable wealth could not be compared to that of the other candidates. "They don't make anything," he shot back. "They get paid exactly what they - " and then he stopped himself. "Forget about it. Next question."
(The question of his tax returns has come up again in his presidential bid; he's promised to release them within weeks.)
As a lifelong Democrat who registered as a Republican to run for mayor, he spent a record $74 million to win the office in 2001, and even more - $85 million - in 2005 for a second term. He won in a landslide over his Democratic opponent, whose campaign spent only $9.5 million, according to campaign finance records.
The financial crisis of 2008 gave the billionaire a compelling reason to lobby for a another four years, which required the city to change its term-limit laws. By the end of the campaign, he had spent $109 million of his own money. The tab for his three mayoral campaigns was the most any individual personally spent to win elected office.
But he was also giving away billions, some of it anonymously. Bloomberg focused on the city's infrastructure, public art projects and public health. He banned smoking in New York City bars, unpopular when it happened until it was roundly embraced.
Between 2001 and 2010, he donated nearly $200 million to the Carnegie Corporation, which in turn funded small programs around the city.
"Anyone who received those grants knew they came from Bloomberg," said Joyce Purnick, author of "Mike Bloomberg: Money, Power, Politics." Critics accused him of using the philanthropy for his own political ambitions - at that point, a third term as mayor.
After leaving office in 2013, there was talk he might settle into a life of philanthropy, entertaining and golf. Instead, he went back to his company, ousted the CEO and took control again.
"The alternative, in my case, is staying home and talking to Diana about feelings," he joked at a panel discussion in 2014. "If that doesn't get you back to work, I don't know what would."
For a few years, he kept busy with his business and philanthropy, then was increasingly drawn into politics. He considered but rejected entering the 2016 presidential race, despite entreaties by fellow billionaires such as Rupert Murdoch. But, horrified by the election of Trump, he gave more than $100 million to congressional candidates in the 2018 midterms. When the president pulled the United States out of the Paris climate agreement, Bloomberg pledged to cover the U.S. contribution, which amounted to $4.5 million in 2018 and $5.5 million in 2019.
In early 2019 Bloomberg launched Hawkfish, a digital voter identification and messaging company that he planned to give to whoever became the 2020 Democratic nominee for president. At the time, he was comfortable with the field, and he accepted former vice president Joe Biden as the likely front-runner and even mentioned advisers for his campaign, suggestions that were ignored. But Biden's lackluster first debate and his poor fundraising worried him, as did Sen. Elizabeth Warren's position on Medicare-for-all. He worried that the large Democratic field wasn't embracing policies strategically and that Trump would beat them in key battleground states.
"That alarmed him, and that's when he decided to enter the race," said a Bloomberg adviser.
His race is a lot like his life: Sweeping, well-funded, luxurious compared with every other Democratic rival. Entry-level staffers for his campaign are paid $72,000 a year, with three catered meals every day, reports the New York Times. The campaign has issued Apple laptops and new iPhones for the thousands of people hired to work in 125 offices around the country. Even his rallies are extravagant: open bars, groaning buffets and lots of free swag.
Whatever it takes to beat Trump.
"It grates on him that a man not nearly as wealthy, not nearly as smart and not nearly as philanthropic became president of the United States," explained another friend. "He thinks he's better than Trump in all those categories - so why shouldn't he be president?"
That, of course, is the $2 billion question.