NEW YORK — In the fall of 2018, Emily’s List had a dilemma. With congressional elections approaching and the Supreme Court confirmation battle over Judge Brett Kavanaugh underway, the Democratic women’s group was hosting a major fundraising luncheon in New York. Among the scheduled headline speakers was Michael Bloomberg, the former mayor, who had donated nearly $6 million to Emily’s List over the years.

Days before the event, Bloomberg made blunt comments in an interview with The New York Times, expressing skepticism about the #MeToo movement and questioning sexual misconduct allegations against Charlie Rose, the disgraced news anchor. Senior Emily’s List officials seriously debated withdrawing Bloomberg’s invitation, according to three people familiar with the deliberations, who spoke on the condition of anonymity.

In the end, the group concluded it could not risk alienating Bloomberg. And when he addressed the luncheon Sept. 24, Bloomberg demonstrated why.

“I will be putting more money into supporting women candidates this cycle than any individual ever has before,” he declared.

It was not an idle pledge: Bloomberg spent more than $100 million helping Democrats take control of the House of Representatives in the midterm elections. Of the 21 newly elected lawmakers he supported with his personal super political action committee, all but six were women.

The decision by Emily’s List to mute its misgivings and embrace Bloomberg as a mighty ally foreshadowed the choice Bloomberg is now asking Democrats to make by anointing him their presidential nominee.

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There are, after all, numerous dimensions to Bloomberg’s persona and record that give Democrats pause. A former Republican who joined the Democratic Party in 2018, Bloomberg has long mingled support for progressive causes with more conservative positions on law enforcement, business regulation and school choice. He has often given voice to views that liberals find troubling.

Yet in a primary campaign defined by Democrats’ hunger to defeat President Donald Trump, Bloomberg is also offering himself up as a person singularly equipped to do so — a figure of unique standing and resources with a powerful set of alliances and a fearsome political machine to draw on. His political rise has become a test of the impact one man’s wealth can have when he applies it to the political system with driving sophistication.

In less than three months as a candidate, Bloomberg has poured more than $400 million, and rapidly counting, into the campaign. But that figure pales in comparison with what he spent in prior years positioning himself as a national leader with presidential ambitions.

A Times examination of Bloomberg’s philanthropic and political spending in the years leading up to his presidential bid illustrates how he developed a national infrastructure of influence, image-making and unspoken suasion that has helped transform a former Republican mayor of New York City into a plausible contender for the Democratic nomination.

Since leaving City Hall at the end of 2013, Bloomberg has become the single most important political donor to the Democratic Party and its causes. His personal fortune, built on a financial information and news company, is estimated at more than $60 billion. It fuels an advocacy network that has directed policy in dozens of states and cities, mobilized movements to take on gun violence and climate change, rewritten election laws and health regulations, and elected scores of politicians to offices as modest as the school board and as lofty as the Senate.

“Clearly, over the last several elections, there has not been a more important donor to the Democratic Party than Michael Bloomberg,” said former Gov. Terry McAuliffe of Virginia, who once chaired the Democratic National Committee. “He has led on guns. He has led on climate change. He has been involved in all these races.”

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In all, Bloomberg has spent at least $10 billion on his charitable and political pursuits. The vast majority has gone to philanthropy, for causes that reflect his personal interests and passions, including $3.3 billion to his alma mater, Johns Hopkins University.

But the Times’ examination — based on a review of years of campaign and nonprofit tax filings as well as interviews with more than 50 people who have benefited from his support — illustrates how deeply that philanthropy is entwined with Bloomberg’s political preoccupations. In fact, in 2019, the year he declared his presidential candidacy, Bloomberg’s charitable giving soared to $3.3 billion — more than in the previous five years combined.

And it is not simply goodwill that Bloomberg has built. His political and philanthropic spending has also secured the allegiance or cooperation of powerful institutions and leaders within the Democratic Party who might take issue with parts of his record, were they not so reliant on his largesse.

In interviews with the Times, no one described being threatened or coerced by Bloomberg or his money. But many said his wealth was an inescapable consideration — a gravitational force powerful enough to make coercion unnecessary.

The Philanthropy Flood

Early in his second term as mayor, Bloomberg bought a six-story beaux-arts mansion on the Upper East Side of Manhattan and outfitted it as part-charity, part-governance laboratory. It has become the hub of his empire — headquarters of Bloomberg Philanthropies and until recently the seat of his political operation.

It was during his 12 years at City Hall that Bloomberg wrote the playbook for propping up allies and co-opting opponents with a mix of political and charitable giving. Even as he spent $268 million on his three campaigns and made $23 million in campaign contributions to others, his philanthropy gave away $2.8 billion, much of it to civic and cultural groups around New York.

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His philanthropy actually comprises three separate streams of money. But only one of them, the Bloomberg Family Foundation, is publicly accounted for. The Times’ examination found billions of dollars in donations under the Bloomberg Philanthropies umbrella that had not been previously disclosed or itemized — corporate giving by his company, Bloomberg LP, and from his personal checkbook.

In all, by his own accounting, Bloomberg has given away nearly $9.5 billion since 1997 at an annual rate that has increased more than a hundredfold. In 2018, the year before he announced for president, he spent nearly $770 million. Last year’s $3.3 billion figure probably included a $1.8 billion donation to his alma mater, Johns Hopkins University, announced in November 2018. Even without it, his charitable giving roughly doubled.

His spending on electoral politics has also steadily increased, from about $11 million in 2013, his final year as mayor, to the more than $100 million during the 2018 midterms.

All of those funds flow not just from Bloomberg Philanthropies and Bloomberg’s super PAC, Independence USA, but through an array of advocacy groups that rely on him for donations in the tens of millions of dollars. A number of them are cornerstones of liberal politics, including the Sierra Club, one of the country’s most influential environmental groups, Planned Parenthood and Everytown for Gun Safety.

The foundation, along with Bloomberg’s other entities, has become something of a talent stable for people he admires — public officials, business leaders and political strategists, among others. The foundation’s board looks almost like a shadow administration, including luminaries like former Sen. Sam Nunn of Georgia and former Treasury Secretary Henry Paulson as well as current or former executives from companies including American Express, Disney and Morgan Stanley.

Much of his charitable giving has been focused in areas like the arts, higher education and global public health. But it has sometimes overlapped with his political agenda, tying him closely to powerful progressive interest groups and amassing reservoirs of gratitude, admiration and influence across the country.

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Howard Wolfson, a senior adviser to Bloomberg, said the former mayor tended to approach his large-scale causes by seeking out trusted partners — political leaders or organizations — and using various parts of his operation to support them.

“When we identify strong, effective leaders, our view is that we should invest in them,” he said.

The range and reach of Bloomberg’s spending, experts said, cannot but play to his advantage in the presidential race.

“The fact that he can call in all these favors all over the country — a normal person can’t do that,” said Adav Noti, chief of staff at the Campaign Legal Center. “A normal person will never be able to do that.”

Policy, the Bloomberg Way

On a national level, there is arguably no issue more closely associated with Bloomberg than gun control. On New Year’s Day 2006, Bloomberg declared that he saw an urgent duty “to rid our streets of guns and punish all those who possess and traffic in these instruments of death.”

That April, he convened a Gracie Mansion summit of 15 mayors from across the country, marking the beginning of Mayors Against Illegal Guns, which within a few short months included more than 100 civic leaders from 44 states.

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Soon enough, Bloomberg ramped up his spending on politics beyond New York. Frustrated at the flow of firearms from Virginia, a state with lax gun laws, Bloomberg tried to buoy candidates in the state’s 2011 elections who shared his views.

After leaving office in December 2013, Bloomberg began expanding his advocacy operation. He founded a new group, Everytown for Gun Safety, which has since spent tens of millions of dollars pushing for gun control measures, with considerable success in swing states.

The organization came into existence through an almost corporate-style merger: Bloomberg already had a gun control group, Mayors Against Illegal Guns, but he needed a grassroots army to compete with the National Rifle Association. So it joined forces with an existing activist group, Moms Demand Action for Gun Sense in America, to form Everytown.

Moms Demand Action had sprung up on Facebook after the 2012 massacre at Sandy Hook Elementary School in Newtown, Connecticut. Volunteers organized into local chapters, held protests and lobbied for legislation. After a year of working long hours for no compensation, many volunteers were running on fumes and well aware their organization needed money.

Bloomberg promised to infuse the movement with $50 million, bringing his mayors’ group and Moms Demand Action under the Everytown umbrella. According to his spokesman, Bloomberg has underwritten the gun control movement with a total of $270 million since 2007. But with his backing came a stark shift in culture, one that left some activists feeling they were pawns.

People involved in the group described being forced to communicate exclusively in canned talking points. Other members greatly appreciated the new direction from Everytown.

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After the mass shooting last year at a Walmart in El Paso, Texas, other groups organized protests to pressure the retailer to change its policies. But Moms members were discouraged from attending and told not to show any affiliation if they did.

“Our goal is always to get results, and sometimes that means playing the outside game, and sometimes it requires playing the inside game and working with partners who have shown themselves to be amenable to change,” said Maxwell Young, chief of public affairs for Everytown.

Bloomberg insisted on a strategy of bipartisanship, frustrating activists who saw the Republican Party as unalterably opposed to their goals. In 2016, he spent nearly $12 million to reelect Sen. Pat Toomey of Pennsylvania, a Republican supportive of background checks but strongly conservative on nearly everything else. In 2018, even as Bloomberg was spending nine figures to defeat congressional Republicans, Everytown backed another Pennsylvania Republican, Rep. Brian Fitzpatrick, for reelection. A number of local volunteers, who said they had been assured that Everytown had no plans to support Fitzpatrick, quit to form their own gun control organization.

But at least a half-dozen former Everytown and Moms Demand Action officials have joined the Bloomberg campaign, including senior political and legal strategists and the deputy director of the Survivors Network.

And when Bloomberg spent roughly $10 million on a Super Bowl commercial this month, he chose to focus his 60-second spot entirely on gun control.

Powerful Alliances

In the presidential race, Bloomberg has activated his sprawling network of allies to great effect — drawing on his foundation and its beneficiaries to build a campaign staff and calling on politicians he has supported in the past for their endorsements.

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It is that network, as much as the raw force of his campaign spending, that has propelled Bloomberg into contention in the Democratic race. He has climbed to the top rank of contenders, even catching up to former Vice President Joe Biden in some national polls.

Since the start of his campaign, more than 50 employees of Bloomberg Philanthropies have moved across town to his Times Square campaign headquarters as paid staff members, including the foundation’s chief executive, Patricia Harris, a former New York deputy mayor, and James Anderson, previously the foundation’s head of government innovation.

Overnight, Harris and Anderson went from providing cities around the country with grants to contacting mayors for support. Dozens of current and former mayors have since endorsed Bloomberg, including leaders from major cities like Houston; Memphis, Tennessee; Tampa, Florida; and Washington.

Bloomberg has promised to spend aggressively to defeat Trump no matter who the nominee is. But advisers to Bloomberg acknowledged the scale and focus of his spending would differ depending on whether he is the Democratic standard-bearer.

“If Mike Bloomberg is the nominee, he will ensure that the Democratic Party has the greatest funding in its history,” Wolfson said.

If Bloomberg is not nominated, Wolfson suggested a narrower focus. “If you’re trying to defeat Donald Trump and you’re not on the ballot, you’re going to focus on the battleground states,” he said.

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There are places where Bloomberg’s past spending has left a less-helpful mark for his campaign. Pennsylvania may be one of them, since some Democrats there still resent his past support for Toomey. But in most places he has ventured as a candidate, Bloomberg’s many years of largesse have helped earn him a warm reception.

During the week of the Iowa caucuses, he toured California with former Los Angeles Mayor Antonio Villaraigosa, for whom Bloomberg spent millions in a 2018 gubernatorial race, and San Jose Mayor Sam Liccardo, a beneficiary of Bloomberg foundation grants. And he got an endorsement from Rep. Mikie Sherrill of New Jersey, for whom Bloomberg’s super PAC spent more than $2 million in the last midterm elections.

Some of his biggest endorsements have come out of cities that have been focal points for his philanthropy. In the Bay Area, Bloomberg’s foundation has distributed dozens of grants to museums, dance companies and climate organizations, while his political donations have funded school board candidates and referendums to tax soda and ban electronic cigarettes. San Francisco’s mayor, London Breed, endorsed Bloomberg last month.

Wolfson said no promises had been made to Bloomberg’s endorsers about what they could expect from him down the line. “I haven’t had a single conversation with anyone where I suggested or implied any future support, nor did anyone ask for it,” he said.