Mayor Bill de Blasio’s quixotic quest for the presidency rests in part on his notion that it takes a New Yorker schooled in the ways of New York bullies to take on the one in the White House.
“I’ve known Trump’s a bully for a long time,” de Blasio said in the video launching his campaign. “This is not news to me or anyone else here, and I know how to take him on. … Don’t back down in the face of a bully. Confront him.”
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When it comes to taking on tough political fights, de Blasio is known more for backing down than for his muscularity. When the mayor decides to challenge powerful adversaries — be they Gov. Andrew Cuomo, Uber or charter school doyenne Eva Moskowitz — he often loses.
De Blasio’s style as mayor may offer a glimpse into how he would govern were he to win his longshot bid for president. The man de Blasio wants to defeat, President Donald Trump, has also staked a reputation on standing up to others, yet frequently changes course when talking directly with strongmen leaders.
Even in de Blasio’s most significant head-to-head battle with the Trump administration, the mayor backed down.
Over the objections of some of his top advisers, de Blasio in January ceded authority over New York public housing to the federal government, home to more than 400,000 low-income New Yorkers.
He did so by inking a deal with federal housing secretary Ben Carson that dramatically expanded federal oversight of the local housing authority without requiring any additional funding from the White House.
Several people involved in the deal described it as a face-saving maneuver — the only way, de Blasio believed, to avoid a full federal takeover of an authority so intrinsic to New York City, and the only way to scuttle the possibility of a criminal trial, following a complaint by federal prosecutors in Manhattan.
But the chair of the agency at the time, government veteran Stanley Brezenoff, publicly excoriated the deal.
“The city and NYCHA have all the responsibility, limited authority and all of the financial burden,” Brezenoff said in February. “That in a nutshell is why I’m against it.”
He called it a federal takeover “in everything but name” and refused to sign it.
“The priority was he didn’t want to be the progressive mayor who lost public housing on his watch,” said someone familiar with the negotiations. “He gave away the house for one thing — maintaining mayoral control in name only.”
It was one in a string of de Blasio defeats.
In June 2015, the mayor used bully-busting language similar to what he’s used against Trump, to describe Gov. Andrew Cuomo. By October, the governor had browbeaten the mayor into dramatically increasing the city’s contributions to the state controlled subway system.
After that airing of grievances against Cuomo, the governor would go on to embrace his reputation for knife fighting. And he would continue to terrorize de Blasio.
“He didn’t stand up to him like he needed to do,” said one former aide, who would only speak on background. “Every once in a while he would dip his toe into an aggressive approach, and then [he] immediately took it out and disappeared.”
Hunter College political science professor Ken Sherrill put it more scathingly: “Cuomo has eviscerated de Blasio time and time again.”
The most significant example of that asymetrical dynamic is also the most recent one: De Blasio this year ceded a sizable amount of control over New York City’s streets to the governor, via the state’s new congestion pricing plan.
The deal that de Blasio endorsed amounts to “one of the biggest political and fiscal heists in modern history,” the Manhattan Institute’s Nicole Gelinas has written.
Through the MTA he effectively controls, the governor, not the mayor, will make decisions on how much drivers pay to enter the tolled cordon around Manhattan’s central business district. The governor, not the mayor, will decide who gets exemptions to those tolls. The governor will determine what the tolling infrastructure looks like on city streets, with what appears to be only nominal involvement of the de Blasio’s transportation department.
And, because the MTA will set these policies, Cuomo will to a great extent determine the very speed of traffic on de Blasio’s streets.
“He ceded a very important part of city governance to a political adversary,” said Gelinas in an interview. “And even if you don’t care about it, you could have used it to get something that you do care about.”
During his 2013 campaign, the mayor singled out one education leader as the personification of all that was wrong with charter schools: Eva Moskowitz, the head of Success Academy with the famously combative personality. After taking office, he followed up on his tough talk by trying to limit her network’s growth.
With an assist from Cuomo, Moskowitz outmaneuvered de Blasio, upstaging an education rally he held in Albany, and ultimately enabling her to continue co-locating her charters with traditional public schools.
“In that case we just decided that it’s not our fight,” said Peter Ragone, a longtime friend of de Blasio’s and a top City Hall aide at the time, who argued the mayor didn’t lose the charter school fight so much as opt out of it on his own terms.
Undeterred, the next year de Blasio picked a fight with Uber, another famously aggressive combatant, in a push to cap the company’s growth. That didn’t work out either. The Silicon Valley unicorn trampled de Blasio with ads in a multimillion-dollar campaign. One de Blasio ally suggested the mayor folded like “a cheap suit.”
Three years later, de Blasio would finally get a year-long Uber cap. By that point, Uber’s fleet in New York City had grown from 25,000 to 85,000 and the company put up significantly less resistance.
As de Blasio has allowed some of his authority over New York City assets to erode, he has declined to take steps that might bolster it and balance the scales.
Council Speaker and likely mayoral candidate Corey Johnson has been campaigning for mayoral control of the New York City subway system, a deft rhetorical gambit and a political longshot. Not only has de Blasio declined to embrace the cause, but during the subway crisis that wreaked havoc on New York City, he seemed to scurry away from the problem, rather than act as as leader eager to help remedy it.
The mayor set up a charter revision commission that took up three causes last year, none of which bolstered his power.
Meanwhile the Council has undertaken its own commission, which the mayor could have stopped. He opted not to, believing the Council would not seek any changes that would limit the mayor’s powers, according to several people familiar with his thinking.
“It’s unimaginable for Bloomberg or Giuliani or any other mayor to sit back while the Council creates a commission which could restructure city government in fundamental ways,” said a city official, who would only speak on background.
To be sure, the mayor has his strengths. As a candidate, he has consistently defied tough odds, winning every election he’s entered. Along the way, he has made measurable changes to New York City — universal pre-kindergarten most notable among them.
A spokesperson for the de Blasio campaign, Olivia Lapeyrolerie, said the mayor “has consistently shown that he won’t shy away from a fight in the name of working people,” and that he “doesn’t back down until he’s delivered on a promise.”
Lapeyrolerie defended de Blasio’s handling of NYCHA and the subways as an example of effective leadership under difficult circumstances.
“The mayor worked closely with the state to pass a plan to fix the subways, and prevented a Trump takeover of NYCHA,” she said. “That’s called good governing.”
Ragone, the longtime de Blasio advisor, argued that de Blasio showed strength when he defeated the rank-and-file police officers’ union at the end of his first year in office, after a gunman murdered two police officers.
With public opinion polls on his side, the mayor leaned on religious figures and the former police commissioner to block what was shaping up to be a work slowdown.
He similarly exhibited strength when he got an initially reluctant Cuomo to fund his signature pre-kindergarten program — even though Cuomo funded it through the state’s general fund, rather than via the millionaires tax de Blasio had sought.
Both of those accomplishments happened in 2014.
“So that required a different series of maneuvers to deal with a formidable adversary who had a different concept of how the program should be implemented,” Ragone said. “With de Blasio you have to start with the objective truth that he has had pretty remarkable accomplishments as mayor.”