Yet less than a year after announcing he was a candidate, Bloomberg was elected the 108th mayor of New York.

And now, two decades later, he is running for president in more or less the exact same way.

To understand how Bloomberg can become president, it is worth considering how he first became mayor—by executing, and succeeding with, a plan no less unlikely than running for president and skipping Iowa and New Hampshire.

“Before he ran, I said to him, ‘Do you know what guys like me do to guys like you?'” said Bill Cunningham, a longtime Democratic operative who became Bloomberg’s top strategist and later his spokesman as mayor. The implication was clear: We fillet people like you—wealthy men with political ambitions—alive.

In 2000 and 2001, candidate Bloomberg forged a path that seemed almost dauntingly difficult, but he pulled it off by recognizing an unusual opening and quickly moving to capitalize on it. It was a campaign that relied on a lot of things going right for him but also made sure that his candidacy was well-positioned to exploit his advantages whenever and wherever he could. It’s not crazy to think he could do it again.



***

Buzz had begun building in the summer of 2000 that Bloomberg, at the time worth $4 billion (now $54 billion), was considering a run for mayor as Rudy Giuliani’s term was ending. The smart play for Bloomberg, it seemed, would be to run as a Democrat. It was the party that Bloomberg belonged to his whole life, and, conveniently for his prospects, Democrats outnumbered Republicans 5 to 1 in New York City. Giuliani wasn’t all that popular, either. In the spring of 2000, he was facing a 37 percent approval rating in New York.

Then Bloomberg polled the prospect of running in the Democratic primary. According to Kevin Sheekey, his longtime political aide, and one of more than a dozen Bloomberg aides and associates interviewed for this story, the poll came back with bad news for Bloomberg’s chances. Beyond the polling, the primary was crowded, and the city’s interest groups, labor unions and civic organizations had been courted relentlessly by other candidates for the previous eight years.

So he decided it couldn’t be done. And so in 2000, with the election more than a year away, he changed his registration to the Republican Party. He began courting Giuliani, having what the New York Times called a “supplicantlike breakfast at Gracie Mansion,” the mayor’s official residence, in late 2000. It was the beginning of a delicate dance that would continue through the election. Bloomberg needed Giuliani’s support, especially in the primary, in which a former top Giuliani administration official, Herman Badillo, represented Bloomberg’s biggest threat in the GOP nominating contest. Bloomberg would often praise Giuliani on the campaign trail, while making clear his differences with someone who, pre-9/11, was running a city that had largely tired of him.

“I am not here to run as Rudy Giuliani,” Bloomberg said at his campaign kickoff, quickly adding, “He has made this city better, and for the groups that don't hate him, he has made the city better based on numbers.”

After 9/11, Giuliani gave a final, tepid endorsement to Bloomberg, one literally so quiet that reporters in attendance could barely hear him, but it was enough to allow the Bloomberg campaign to run ads of the two of them on television in a near nonstop loop.

In addition to wooing the Republican mayor, Bloomberg made another adroit move to assure wary Republicans of his devotion to his new party: He donated money to the five county Republican parties in New York City. The amounts were not huge, but for county parties no one much paid attention to, they were enough to bring loyalty. And Bloomberg wooed Roy Goodman, a patrician state lawmaker and head of the Manhattan Republican Party, and Guy Molinari, an old-school machine politico who was then the most powerful Republican on Staten Island, New York’s most Republican borough. Molinari literally taught Bloomberg how to kiss babies, demonstrating for him at a Beatlemania tribute concert and fireworks display on the island’s South Shore—“The first thing you have to learn as a candidate,” he said—even as he got slammed by conservatives for backing a left-leaning Democrat in everything but his new voter registration.

But Bloomberg mostly kept his distance from New York’s party politics. He grabbed the endorsements of the county parties before he was an officially declared candidate, and he didn’t even bother showing up when the groups officially backed him. His campaign said it was because he was traveling and didn’t know the endorsements were coming, but it is hard not to notice that it was part of a deliberate strategy on the part of the businessman to keep his distance from party politics as much as he could.

When Bloomberg was endorsed by the Manhattan Republican Party, a group that considered its prerogative to set the direction of the GOP for the rest of the city, it turned into something of a fiasco, one of the rare party endorsements in New York political history in which the major players couldn’t agree on basic facts or even bother to stand side by side with one another for a photo op. “We didn’t pull a rabbit out of a hat today,” Goodman told the media after the endorsement, disputing the candidate’s account that the timing was a surprise. But the party released a news release calling the mogul “an authentic mensch” who was a “warm and caring human being.”

“He made it very clear that he was running on the line because it was available, and that he didn’t agree with a lot of Republicans,” said William F.B. O’Reilly, a prominent party operative. “He made the rounds, he did what was required, but he really wasn’t into any party stuff. He never even appointed a Republican judge, but on the other hand he never said that he would.”

New York’s unique voting laws meant Bloomberg didn’t just run as a Republican, he also sought the Independence Party line. The group was controversial: Among its leaders were Lenora Fulani, an activist who had made a series of inflammatory remarks, including that “Jews are mass murderers of people of color,” and Fred Newman, a psychotherapist who has been accused of operating a “therapy cult” that encouraged sex among therapists and patients.

“He was very personal and very approachable, and I know that is not his reputation,” said Jacqueline Salit, one of the leaders of the party. Salit and others met with Bloomberg at Bloomberg L.P. offices, and afterward he sent her and others a copy of his memoir along with a handwritten note. The Liberal Party and the Conservative Party had both rejected Bloomberg’s candidacy, but he relentlessly courted the independents, visiting Staten Island for a breakfast with party leaders there and sitting for a screening-committee interview at the midtown Hilton.

The Independence Party’s most important criterion for deciding whom to nominate was a candidate who would support nonpartisan city elections. As a Democrat-turned-Republican running in a heavily Democratic city, Bloomberg shared this view. He pledged to push for a citywide referendum to get it passed. He gave the party $250,000, and the day after he announced, he was officially a candidate (through a massive blitz of television advertisements that ran while Bloomberg was out of the city attending his daughter’s graduation from Princeton University) he appeared on the steps of City Hall and made nonpartisan elections his first policy proposal as a candidate, a proposal that led John del Cecato, the spokesman for one of Bloomberg’s Democratic opponents (and currently a strategist working on Pete Buttigieg’s presidential campaign) to quip to the media, “If my poll numbers looked like his, I’d call for nonvoter elections.”

In the end though, Bloomberg and the Independence Party seemed to know what they were doing. Bloomberg got 59,000 votes on the Independence line, largely if not primarily from Democrats and liberals who blanched voting Republican. He won the race by fewer than 35,000 votes.

Bloomberg preferred to throw money at political consultants—some of whom made upward of half a million dollars on the race—to the scutwork of campaigning. As early as the summer of 2000, the rest of the field was in full campaign mode. Mark Green, the eventual Democratic primary winner, was passing out palm cards for Al Gore and Hillary Clinton on Election Day 2000 with the words “Next Year, Make Mark Green Mayor” scribbled across the top, while even by the end of 2000 Bloomberg was still dithering on whether to enter the race. A few days after Christmas, Bloomberg delivered chicken breasts, potatoes and peas as part of Meals on Wheels, an appearance that was promoted by Bloomberg. L.P. in an official release, but which led to Bloomberg chastising the political media when they showed up to ask questions. “This isn’t a campaign stop,” the mogul said, acknowledging, “It’s very flattering that people think I am a legitimate candidate.”

Once Bloomberg became an official candidate, his skills as a candidate scarcely got better. He would disappear from the trail for long stretches of time, but it was more of a problem when he reappeared. He praised Hillary Clinton’s campaign skills as he tried to consolidate Republican support. At an endorsement news conference alongside Gov. George Pataki, Bloomberg repeatedly called himself a liberal—the very epithet Pataki had used to pound Mario Cuomo into submission in his first race in 1994—as the governor stared on in silent astonishment. Bloomberg’s aides abruptly cut the news conference short, leaving Pataki alone to answer questions, but then promptly brought Bloomberg back when they realized the visuals of the governor alone at the podium didn’t look right.

Public polls had Bloomberg down by 16 percentage points in the race’s final weeks. His aides insisted that private polling had him down only 12. And those weeks were consumed with Bloomberg’s inability to explain why his company had done business in South Africa, a charge that led him to accuse Green of playing “the race card” and with Bloomberg’s accusation that Green, a rather conventional Upper West Side liberal, was an apologist for Josef Stalin.

But if the candidate could seem erratic, the campaign was not. Bloomberg cleverly made a hard play for black and Hispanic voters turned off by Green, who was accused of running racially coded advertising in the Democratic primary. Young aides likened the campaign, and each of his subsequent races, to working on a presidential campaign, with a virtually around-the-clock war room, campaign staff deployed to handle even the smallest neighborhood media outlets and constant care and feeding of important allies.

Bloomberg spent $69 million on his first mayoral race. To put that figure in perspective, it was more than Ross Perot spent to run for president 10 years earlier. His campaign ran ads featuring Giuliani’s endorsement of Bloomberg during the late innings of the World Series between the Yankees and the Arizona Diamondbacks, sent dozens of glossy mailers on high-quality paper into the homes of millions of New Yorkers, and even sent video cassettes of the mayor to targeted homes. When it was over, Bloomberg had spent more than $90 per vote.



***

After Bloomberg won, by more than 2 points, Democrats were left stunned at their own ineptitude. Dennis Rivera, a prominent labor leader in the city, said the party was in “an incredible crisis” and that it treated minority voters like “battered women.” Freddy Ferrer, the Bronx borough president who lost a divisive runoff to Green, said the “party had been taking people for granted,” and he sent shock waves through the party’s upper ranks by meeting Bloomberg for breakfast the day after the election.

Bloomberg had replicated in many ways Giuliani’s coalition, but he made clear as mayor that he was going in a different direction. On election night, a few hours after Bloomberg was declared the winner, he had a top aide, Jonathan Capehart, put a call in to Al Sharpton. The civil rights leader had clashed repeatedly with Giuliani—and was a more controversial figure in 2001 than he is today. Giuliani saw that attacking Sharpton was key to firing up his base. Bloomberg said he wouldn’t do that. “I know you have not been welcome at City Hall over the last eight years,” Bloomberg told Sharpton. “You and I aren’t going to always agree but we are always going to have a dialogue.”

The next night was the annual gala for 100 Blacks in Law Enforcement Who Care, an organization of members of the Police Department who advocated for better relations between police and minority communities, and Bloomberg, who had just won election to America’s largest city, asked Sharpton for permission to go and pay his respects.

“He wasn’t playing to that Rudy/Trump crowd,” Sharpton said. “He wanted to show that he was going to be a different kind of a mayor. He wanted to manage the city and he didn’t think racial discord was a good way to manage the city. Rudy didn’t care about managing the city, he just cared about managing his image and making sure he was going against people he wanted to go against.”

Bloomberg showed up in January with former Mayor David Dinkins at Sharpton’s annual Martin Luther King Jr. Day celebration in Harlem and pledged to come back every year. Over the years, Sharpton led protests against some of Bloomberg’s policies, most notably stop and frisk, and he backed each of Bloomberg’s Democratic opponents, but Bloomberg kept his word and even donated money to the education arm of Sharpton’s National Action Network, and, according to Sharpton, never once asked for his endorsement.

“He would tell me, ‘I know you are the opposition,’” Sharpton said. “I think his calculus was that if he kept reaching out, and I refused to work with him, I would look unreasonable, and he would look like the person trying to get things done.

“He was just more secure in who he was than most politicians you meet,” Sharpton said, noting Bloomberg would often face a hostile crowd at Sharpton’s headquarters. “Most politicians can’t handle being heckled. He just kept coming back anyway.”

Looking back it can seem almost as if, early in his first term, Bloomberg tried to be as unpopular as he could to give his approval ratings a chance to recover in time for his reelection bid. In his first term, he raised $3 billion worth of new taxes, primarily by a massive property tax increase and a progressive income tax that raised taxes on those making over $100,000 a year, and he raised them further on people making more than $500,000. He proposed cuts across city agencies, including for police and firefighters, which were considered sacred after 9/11. He cut the city’s recycling program, library hours, senior centers and ambulance shifts. Most alarmingly for budget wonks, Bloomberg proposed borrowing $1.5 billion to cover the hole in the budget, raising fears the city would go back to the dark and deeply indebted days of the 1970s.

He pushed for nonpartisan elections, as he promised the Independence Party he would, a move that consolidated the entire Democratic establishment against him. Bloomberg spent millions on the effort, but it was badly defeated in a citywide referendum. He passed a smoking ban in bars and restaurants. He lobbied both the Democratic and the Republican parties to hold their conventions in New York, and then endorsed the highly unpopular (by New York residents, at least) George W. Bush when the GOP chose New York City. By mid-2003, Bloomberg’s approval rating in the city had dropped to 32 points. It was the lowest approval rating any mayor had received since 1993, the last year of the Dinkins administration.

“I understand what the public wants,” Bloomberg insisted to a reporter midway through his second term, as his approval numbers hovered near historic lows. “I am not out of touch at all.”

Eventually, Bloomberg’s numbers began to rise. A booming economy helped, and Bloomberg’s billions did too. Besides the donations to political entities, Bloomberg showered cultural groups and nonprofit organizations with his own money, filling in holes that had been cut by his budgets. On the eve of his reelection, the subway system announced an unprecedented fare cut for the last six weeks of the year, something that was widely seen as a boost to the mayor’s prospects. Hours before his first debate with Democratic nominee Ferrer, Bloomberg announced that there was a credible terror warning against the city’s subways and declined to participate in the debate, leaving Ferrer to spar with an empty podium. It looked like the mayor was using the threat of terror to get out of his civic obligations, but after spending $102 million of his own money, he won in a landslide.

Four years later, Bloomberg decided he wanted to run for a third term, even though city voters had twice voted in a referendum for a two-term limit on all elected officials in the city. But the way he went about it revealed how he had learned to move his agenda. Rather than begin a public marketing campaign, the mayor met privately with the owners of the city’s three daily newspapers—Arthur Sulzberger of the Times, Mort Zuckerman of the Daily News and Rupert Murdoch of the New York Post—and convinced them of the wisdom of the move. Then he met with Ron Lauder, a fellow billionaire and the heir to the Estée Lauder empire, who had made term limits his pet cause, and persuaded him to grant Bloomberg a one-time exemption. His administration rallied social welfare organizations that had benefited from Bloomberg’s money and worked wavering city council members over one by one until Bloomberg had enough votes to announce that he would, in fact, run again.



***

It is hard not to see in this tale how Bloomberg would campaign, and how he would govern were he to win. Just like he determined that he could not win a Democratic primary in 2001, so Bloomberg has determined that he can’t win in the first four primary states, and so is relying on another path. His aides say he was the first candidate in history to personally register for the nomination in Arkansas, and while the rest of the field can resemble a children’s soccer game, chasing after the ball wherever it lands, Bloomberg will follow a path through delegate-rich states like California and Texas, places that don’t often see the kind of full-throttle campaign resources his team believes it can bring.

And his campaign believes he has a story to tell that will at least get liberal Democrats to give him a look. It is not just on guns, immigration and the environment, either. Despite his push for a third term, Bloomberg has made a name for himself a political reformer, pushing for nonpartisan elections outside New York as well as inside. It is easy to imagine him calling for filibuster reform, or strengthening voting rights, or even adding a Supreme Court justice. His comments over the past several years defending Wall Street have gotten him in trouble, but his aides point out that not only did Bloomberg raise taxes in a way that no other candidate in the field has, but he also built 185,000 units of affordable housing (a figure that essentially means building another South Bend, Indiana, and still having tens of thousands of housing units to spare), lowered the racial temperature in a city reeling from 9/11 and eight years of Giuliani, defended the right of Muslims to build a mosque near ground zero, drastically raised teacher pay, reduced the city’s prison population by 40 percent, mounted an aggressive anti-poverty campaign that recalculated the city’s poverty rate to allow more people to receive federal benefits, and spent $3.1 billion on new school construction.

“The argument is going to be, ‘You can listen to what other people say they are going to do, or you can look at what Mike actually did,’” one adviser said.

None of which is to say that Bloomberg can win this thing. Eight million things had to go right for Bloomberg to become mayor—a divisive Democratic primary, a flawed opponent, the shock of 9/11, a city scared of what a return to the days of Democratic rule might mean. But his team knew what they could do to position themselves to win, how to run straight through the narrow opening that led a virtually unknown rich guy to City Hall.

That race looked impossible to win. And this one does too. Which isn’t to say that Bloomberg has a good chance of winning. He doesn’t. But he doesn’t have no chance, either, not in a party or a nation as unsettled as this one.