NEW YORK -- Michael R. Bloomberg sat stone-faced behind an ornate desk at City Hall, as speaker after speaker berated him for 4 1/2 hours.
"I may not be able to vote yet, but I know for a fact that what you are doing is wrong," a 14-year-old from Brooklyn told him. "Quite frankly, Mayor Bloomberg, you are cheating."
It was Nov. 3, 2008, the day before Barack Obama was elected president. The economy was in a deep recession. Bloomberg's second term was near its end, and, against the advice of some of his closest advisers, he had strong-armed a divided City Council to extend a two-term limit that had been imposed by voters, so that he could run again. New York, he declared, needed him.
Before he could sign that extension into law, he had to endure days of withering face-to-face criticism from New Yorkers who accused him of hypocritically circumventing democracy. Bloomberg also paid a price: In 2009, he barely squeaked to a third term over a fairly weak opponent. And that was after spending $100 million of his own money.
It was audacious, humbling and ultimately successful. Bloomberg now hopes to parlay his largely successful tenure as mayor of the nation's most populous city, along with his heavy spending on progressive causes like curbing gun violence and mitigating climate change, into a successful bid for the Democratic nomination for president.
Bloomberg's strategists are modeling their effort on his long-shot race for mayor in 2001. He was initially dismissed as yet another rich person indulging with politics as a hobby. Bloomberg turned that perception around by spending generously on direct mail and TV ads. He also convinced voters that his Wall Street experience and entrepreneurial ability were assets. The uncertainties of the 9/11 attacks, Bloomberg's enormous spending and a last-minute endorsement from the incumbent mayor, Rudolph W. Giuliani, helped push him over the line.
Bloomberg used about $74 million of his fortune for his race in 2001, $85 million in 2005 and $102 million in 2009. With a net worth estimated at $54 billion, he can easily burn through multiple times the $1.6 billion that Donald Trump, Hillary Clinton and their allies spent in total during the 2016 presidential campaign. Since he announced his candidacy on Nov. 24, Bloomberg has spent more than $60 million advertising on TV, cable and social media, according to Advertising Analytics, an ad tracking firm.
Still, even his admirers acknowledge that winning a national Democratic primary will be a uphill battle. Bloomberg is a billionaire seeking favor among Democratic voters who are deeply worried about inequality in income and wealth. His commitment to the party is tenuous: A longtime Democrat, he became a Republican so he could face a less-competitive primary when he ran for mayor in 2001, and then declared himself an independent in 2007 before returning to the Democratic Party last year.
Moreover, no New York City mayor has ever been a major-party nominee for president, though several -- John V. Lindsay in 1972, Giuliani in 2008 and the current mayor, Bill de Blasio, this year -- have tried.
Having thrice decided against running for president -- in 2008, 2016 and most recently in March -- Bloomberg changed his mind in November, when surveys conducted by his and other pollsters showed President Donald Trump with a strong chance of winning six swing states that could likely decide the 2020 election.