“Do not mistake the two sides of Michael Bloomberg. When it comes to the environment and public health, he is an interventionist. When it comes to economics he is a pure free marketeer,” de Blasio, who is backing Bernie Sanders, said in an interview with POLITICO this week. “He vehemently opposed using the tools of government to address the most profound economic crisis of our times.”

As a mayor who took office months after Sept. 11, Bloomberg reimagined New York City as a chic metropolis with gleaming towers rising along the once-industrial waterfront and atop rail yards. But as a presidential candidate, neither that vision nor his alignment with Democrats on climate change, immigration and gun control was enough to shore up his chances at a moment when the Democratic party’s progressive wing was on the rise. Recognizing that, Bloomberg has proposed a tax increase on high earners like himself, called for stronger union protections and promised to double spending on homelessness.

“I believe America should always be a country where a middle-class kid like me can start a business and succeed beyond her or his wildest dreams. But just as important, America must always be a place where the middle class grows bigger and stronger,” he wrote in a New York Times op-ed last month. “Right now that’s not happening, because the rewards of the economy are far too concentrated at the top.”

His team is quick to point out he drove up graduation rates and test scores, which improve earning potential, established a commission to tackle poverty and expanded tax credits. They argue New York City bucked national trends by holding the line on poverty better than other major American cities during his tenure.

"From successful efforts to improve schools and narrow achievement gaps, to our groundbreaking financial empowerment initiatives, eliminating inequality and providing economic opportunity was at the heart of everything the Bloomberg administration did,” a campaign official said in a prepared statement. “New York City's economy became more diverse and inclusive with Mike as mayor, and the same will happen for America with Mike as president."

But his data-driven policies and dispassionate rhetoric on poverty over the course of his mayoralty disaffected low-income pockets of the city. He vetoed bills to require paid sick days for private-sector workers and higher wages at companies receiving city subsidies, arguing it was akin to “a big managed economy [like] the USSR.”

“What he is saying now, as he is running for president, is much different than what he did when he was mayor,” said Stuart Appelbaum, president of the retail workers union that advocated for the wage measure. “I’m disappointed that when he had the power to do something about it as mayor, he was not supportive of living wage or paid family leave and instead chose to veto both bills.”

His mayoralty was embraced by New York's wealthy and elite, who applauded his grandiose vision for rebuilding a city devastated by the terror attacks. But as he was supporting developments with high-end homes and shops — albeit alongside a city-funded affordable housing program — his appointees to a local board were raising rents on regulated apartments during the recession.

That wasn’t the only aspect of Bloomberg’s record that has long troubled advocates for low-income New Yorkers. By the beginning of Bloomberg’s final year in office in 2013, living conditions for more than 400,000 public housing residents had so deteriorated that the New York City Housing Authority’s repair backlog exceeded 420,000. He vowed to tackle it, and a year later, NYCHA reported a reduction to 106,000 repairs.

But it had all been sleight of hand, a U.S. attorney’s office investigation later found: Agency workers had come up with ways to “manipulate” the numbers, rather than actually fix apartments.

Investigators also discovered that during Bloomberg’s third term, the agency began submitting false information to the federal government to certify its inspectors were doing required lead paint checks while actually skipping them, leaving children to reside in apartments with contaminated paint.

“He didn’t believe housing was a responsibility of city government, or government in general, which is why there was little to no attention paid to NYCHA until it blew up into a full blown crisis towards the very end of his administration,” said state Sen. John Liu, who served dual roles as city comptroller and permanent critic during Bloomberg’s time in office.

The damning investigation released by U.S. Attorney Geoffrey Berman in 2018 led to the appointment of a federal monitor last year. The documented failures — mold, rats and leaking ceilings — spanned the Bloomberg and de Blasio administrations. Housing professionals generally agree that decades of federal disinvestment were exacerbated by local management flaws.

In Bloomberg’s case, critics said the agency that housed predominantly poor, black and Latino families never appeared to be a priority.

“No one had taken real responsibility for NYCHA over many decades, and that includes Bloomberg,” said Ray Lopez, a leader of Metro IAF, an advocacy organization whose 2013 lawsuit over mold in public housing led to a consent decree in the last month of Bloomberg’s tenure.

Some tenant leaders give Bloomberg credit for lending an ear, despite the troubling conditions.

“When he was mayor he listened to the residents of public housing,” said Danny Barber, head of the Citywide Council of Presidents, who said he appreciated Bloomberg’s business-like approach to government. “The follow through on his behalf could have been better.”

Bloomberg also stoked anger when he appointed John Rhea, a former investment banker with no prior housing experience, to run the housing authority. His budgets contributed comparatively little in capital funding for the agency, and in many years the city collected more from NYCHA in payments in lieu of taxes than it gave the agency in expense funding. (De Blasio stopped requiring NYCHA to make those payments.)

In 2013, staffers were allowed to close work orders by reporting a resident wasn’t home when a maintenance worker arrived, leading to 200,000 repairs being removed from the backlog without real fixes. Residents would sit around with their doors propped open waiting for workers to arrive, only to find that their complaint had been closed because they were falsely marked as not home, Lopez said.

Starting in 2011, NYCHA falsely certified to the Department of Housing Preservation and Development that it was conducting required lead inspections — a practice that continued until 2016, federal prosecutors found. More than 1,100 children living in NYCHA apartments were found to have dangerous levels of lead in their blood between 2012 and 2018.

The lead deception became public during de Blasio’s tenure and ballooned into a full-fledged scandal, leading to the resignation of his NYCHA chair Shola Olatoye.

“It was a mounting problem under the previous administration,” Liu said. “The pipes were already leaking and finally burst under the current administration.”

New York’s homeless population also skyrocketed during Bloomberg’s time in office.

The number of people sleeping in city shelters soared to more than 53,000 by January 2014, a month after he left office, from 31,000 when he began, according to reports from the Coalition for the Homeless.

“Every time I pass a homeless person on the street I can’t help but think that the current crisis we’re facing right now has deep roots in his administration,” said Mary Brosnahan, who headed the coalition during his administration.

The sky-high cost of housing in New York combined with an economic crash and policy decisions to force more and more families into shelters. At the beginning of 2014, there were more than 22,000 homeless children. Families were staying in shelters longer than ever before, an average of 14.5 months.

A turning point came when a rental-assistance voucher program was terminated in 2011, after the state withdrew aid.

Bloomberg and his aides suggested at the time that some families were intentionally moving into shelters in order to qualify for the subsidy. Later, he said families extended shelter stays because they were “pleasurable,” even as residents complained of rodents, dirty rooms and spoiled food.

“We had a financial meltdown in ‘08 and a recession in ‘09 and ‘10, and any policy hobbyist knows that after a recession, homelessness is going to go through the roof. People lose jobs. They’re not able to hold onto their homes. And yet there was zero preparation for that. There was zero preparation in anticipation of a rise in homelessness,” Liu said.

Bloomberg’s team stresses that the number of homeless people sleeping on the street declined during his tenure, and he signed a deal with the state to create thousands of apartments for people in need of social services.

But he also moved to tighten the rules to get into homeless shelters, requiring single adults to show proof they had nowhere else to go.

The City Council successfully sued to block the rules, calling them “cruel and punitive.” The administration also tried to require shelter residents with jobs to pay rent, but ultimately backed down and agreed to instead create a new savings program.

Brosnahan recalled appearing with Bloomberg at a press conference on the deal and hearing him talk about the need to teach homeless people how to save. “It was so tone deaf and I think telling of this guy’s mindset,” she said. “Anything having to do with there the rubber meets the road for our poorest neighbors, he didn’t put much energy into whatsoever.”