Bill de Blasio, the Failure King of NYC
How a progressive reformer turned into America's most hated mayor.
Welcome back to What Went Wrong?, a newsletter about the failures, inefficiencies, and screw-ups that define 21st-century American life written by Harry Cheadle. This one is long, but as you’ll see we have a lot to get through. Above photo of Bill de Blasio in 2015 via the TechCrunch Flickr account.
I couldn't write a newsletter that covers failure without talking about Bill de Blasio. The New York City mayor makes errors the way Jackson Pollack used to paint, in great sweeping savage movements and violent dribbles. He bumbles, he flails, he blames others, he reverses course without acknowledging it, he inspires hatred and contempt among his ideological allies as well as his natural enemies. He's a six-foot-five monument to hubris and petty grievance, an infamously bad manager who alienates the people who work for him and many of the people who voted for him, a politician so widely despised that you'd almost feel bad for him if you didn't yourself hate the guy's guts.
A lot of public officials have done a poor job of handling the protests of George Floyd's killing by a Minneapolis cop, which have been met by a notably brutal response from many police departments, including New York’s. But de Blasio stands out because several years ago he was once one of the country's most touted liberal reformers. In 2013, he ran for mayor on the premise that New York had become “two cities” under billionaire mayor/wannabe king Michael Bloomberg. If the city continued its trajectory, he warned in one speech at the New School, it would become a “playground for the rich” where “a privileged few prosper, and millions upon millions of New Yorkers struggle each and every day to keep their heads above water.”
During a contentious Democratic primary, he highlighted his progressive plans for affordable housing and universal pre-K as well as his Black wife and Black children. Here's one ad, featuring his son Dante, that drove the point home:
When he defeated frontrunner City Council Speaker Christine Quinn in the Democratic primary, effectively winning the mayor's office, he was praised by liberals from around the country, who saw him, the New York Times wrote, as “a champion of their values who is also a shrewd and cunning practitioner, stepping into office at a time when the national debate over inequality and social justice has reached a fever pitch.” He was a former left-wing radical who had once supported Nicaragua's Sandinista government and also a Democratic establishment operative who managed Hillary Clinton's 2000 Senate campaign. His victory seemed like a rejection of the Bloomberg years, during which the city got sleeker and shinier at the expense of people of color targeted by the NYPD and pushed out of their neighborhoods by gentrification. Many people looked upon the approaching de Blasio era with genuine optimism.
“He could have been the guy,” Scott Stringer, the city comptroller and a potential de Blasio successor, told the New York Times Magazine last year. “The opportunity was right there.”
Seven years later, de Blasio is being roundly condemned for his stubborn and bizarre refusal to blame the New York Police Department for anything, even as its officers employ shocking amounts of force against even completely peaceful protesters. He was recently grilled by WNYC journalist Brian Lehrer and listeners who called in to his radio show during what the New Yorker called “a thirty-minute performance of defensiveness, denial, and bizarre false equivalence.” The police unions, who have openly hated de Blasio for years, haven't stood up for him; instead, one police union revealed his daughter's personal information after she was arrested at a protest. Even his staff has turned on him: Last Wednesday, dozens of his former and current staffers wrote an open letter demanding a variety of policies and claiming de Blasio “is on the brink of losing all legitimacy in the eyes of New Yorkers.”
De Blasio has endured many scandals and screw-ups during his two terms, but this seems like a capstone to a mayoralty that will probably be regarded by history as a bust. I've been reading extensively about his time in office during the past week, and it seems like there are three broad schools of thought when it comes to de Blasio and his many failings, at least among progressives. It’s instructive to take a tour through them:
Option 1: De Blasio is good, actually
Not many people are willing to defend de Blasio right now, but over the years some commentators have emphasized his accomplishments rather than his failures. Left-wing journalist Juan González's book Reclaiming Gotham situates de Blasio as part of a wave of progressive mayors elected around the Western world after the financial crash and recession of 2008. I haven't read the book, but reviews say that while it doesn't offer a blanket defense of the mayor, it points to policies that have successfully redistributed wealth to the working classes. In a 2017 talk, González said that thanks to de Blasio's successful effort to effectively freeze increases on rent-stabilized apartments in his first few years, tenants saved roughly $2.1 billion when compared to the 40-year average of 3.2 percent annual rent increases.
It’s undeniable that the city has changed in some ways for the better in the past several years: Around the time of de Blasio's first term, New York City also moved to provide pre-K education for all children, became the largest U.S. city to mandate paid sick leave for most workers, and ended “stop-and-frisk” policing, which unfairly targeted people of color.
These policies have done a great deal of good for the poorest New Yorkers, which may explain why de Blasio has polled better among Black people than white people. They also form the bedrock of the narrative that de Blasio has been a relatively successful mayor who attracts ire for sometimes petty reasons. “De Blasio’s issue largely seems to be one of style,” one largely pro-Bill 2019 Vox piece explained, adding, “De Blasio can come off as sanctimonious, arrogant, stubborn, and preachy about the gravity and scope of what he’s doing.” The story also noted that de Blasio famously has continued to work out at a Park Slope gym miles away from City Hall, a habit that has inspired countless tabloid stories. Other controversies are less easily dismissed—for instance, his failure to fire Daniel Pantaleo, the cop who put Eric Garner in a fatal chokehold, until five years after the incident—but de Blasio fans have frequently insisted there's more good than bad.
“It's usually the case that contemporary observers are less generous than historians,” former New York City Mayor David Dinkins (who de Blasio once served as an aide) told VICE in 2017. “People later will reach back and say a lot of nice things about him that they may not be saying now.”
Option 2: Even the mayor can't beat the system
Another way to look at his tenure is to point to places where he's failed, but note how many obstacles stood in his way. Take the killing of Eric Garner in the summer of 2014. After a grand jury declined to charge Pantaleo that December, de Blasio gave a news conference in which he said he told his Black son to “take special care” around police officers because he was at greater risk of being killed by them. That seems like an uncontroversial thing to say—parents of Black kids have had to give them “the talk” about cops and racism for decades—but it enraged New York's reactionary (and politically powerful) police unions.
When two NYPD cops were shot and killed later that month, Police Benevolent Association head Patrick Lynch said their “blood on the hands starts at City Hall in the office of the mayor.” At their slain colleagues' funerals, some officers turned their backs on de Blasio as he spoke in a gesture of contempt. The following month, the number of arrests and tickets dropped in what appeared to be a work slowdown by the NYPD.
According to the New York–based outlet City & State, this brouhaha likely scared the mayor away from police reform and led to him steadfastly supporting the cops during the George Floyd protests. One revealing quote from that story:
“De Blasio meant what he said when he vowed to change the NYPD,” said one former de Blasio speechwriter, who requested anonymity to speak frankly. “But then he tried, and there was infinitely more pushback than he'd anticipated. Maybe the most powerful force in the municipal government openly revolted against him, and it terrified him. It has ever since.”
You could tell a similar story about de Blasio's efforts to build affordable housing, which the mayor's office often touts as a success. From 2014 to 2019, city government efforts created 135,437 affordable units, and though critics have accused de Blasio of not creating enough housing that low-income and homeless people can actually afford, it's also true that real estate prices and changes to federal tax policy have made the building of such housing very expensive for the city. And though he was widely criticized for working with (and soliciting donations from) real estate developers, you could argue that you have to work with developers to build anything, and that de Blasio is a pragmatist focused on getting things done.
The mayor has compromised and even surrendered ground on various fronts, but these moves could be excused as hard decisions made under duress. You have to prevent a full-scale police rebellion. You have to build new affordable housing by any means necessary. A 2017 Harper's story that explored the reasons for de Blasio's unpopularity posited that his “curse” was “to often suffer the consequences of doing the right thing. He has an almost tragicomic genius for finding political injury in well-intentioned policies.”
Even de Blasio’s harshest critics have to admit that not everything that goes wrong in New York City is his fault. The New York State government bears responsibility for a lot, including the city’s atrophying subway system and (at least in part) the region’s lackluster response to COVID-19. There has been a long-running feud between the mayor and Governor Andrew Cuomo that no doubt makes it more difficult for the state and city governments to cooperate on problems like a pandemic, but de Blasio can’t be blamed entirely for that conflict, right? And sure, he tried and failed to get progressives elected to the state legislature, but wasn’t it a noble effort? Can’t a guy get points for effort?
Option 3: What if he is just an utter incompetent?
The above two narratives may be too generous, however. No one doubts de Blasio is more progressive than the two mayors who preceded him, and he certainly has an extraordinarily difficult job. But what if he was just spectacularly unsuited for that job from the start?
When he won the 2013 Democratic primary, he was helped by several of his rivals self-imploding, pointed out Harry Siegel, a Daily Beast editor and New York Daily News columnist who closely follows city politics. City Comptroller John Liu, who Siegel described as the “real progressive in the race,” was dealt a severe blow when the Campaign Finance Board denied him $3.5 million in matching funds over some campaign finance violations. Anthony Weiner's campaign collapsed because of his second sexting scandal. De Blasio ended up with a “double-wide lane” in the race, Siegel told me last week, and wound up winning an office he couldn't properly fill. “Look, I think that the guy was never worthy to start with,” he said of de Blasio.
Siegel pointed to several outright hypocrisies on the mayor’s part. In 2011, de Blasio denounced Bloomberg's eviction of Occupy Wall Street as “needlessly provocative and legally questionable"; in the past week he has praised a shockingly heavy-handed police response to the George Floyd protests. As a mayoral candidate, he got arrested on camera in a protest against the closing of Long Island City Hospital; as mayor he claimed he had reached a deal that "kept the wolf from the door" but the hospital closed anyway, leaving community activists with a bitter taste in their mouths. He even flip-flopped on a plan to build condo units on top of a public library in Brooklyn that he had derided before he became mayor. Here's how Harper's described it:
When the idea was floated during the Bloomberg years as part of a proposal to modernize the city’s library system, de Blasio attacked it as a venal corporate plot to transform places of “knowledge and learning” into profit centers for Big Real Estate. “Once again,” he said, “we see lurking, right behind the curtain, real-estate developers who are very anxious to get their hands on these valuable properties.” But after the deal was struck, de Blasio, now mayor, got behind the project. The library chose a firm called Hudson Companies for the job. The firm was run by David Kramer, the mayor’s friend and fund-raiser.
(Sales for condos atop the library began in 2019; the cheapest one-bedroom available was over $1.1 million.)
It's hard to look at his record and not conclude that the mayor is a weathervane, a black plastic bodega bag being tossed by the wind with no control over where it goes. An old Times examination of his record as Clinton's campaign manager described him as “indecisive,” “conflict-averse,” and “agonizingly inefficient,” and you can see those characteristics play out in his administration. He aggressively courted national media attention even while he was botching responses to controversies closer to home. He's been repeatedly investigated for accepting donations to his nonprofit from people with business before the city. He has showed up late for countless events, including a memorial for victims of a plane crash. He once dropped a groundhog at a Groundhog Day ceremony and the animal died shortly afterward. In 2015, he tried to hold a forum in Iowa for Democratic presidential candidates but had to cancel it after no one wanted to come.
Aides have left his service with clear feelings of unhappiness. Rebecca Kirszner Katz, once describe as “the fifth member of our immediate family” by the mayor, quit in 2015 and told the Times Magazine last year: “I’ve been defending de Blasio’s record for years… I stopped defending his choices a long time ago.” Another former adviser called the mayor’s choice to visit that infamous gym as the pandemic hit New York “pathetic. Self-involved. Inexcusable.”
Even De Blasio's biggest accomplishments don't stand up especially well to scrutiny. During his 2013 campaign, the plan was to finance his universal pre-K scheme with taxes on the rich. But that tax plan was rejected by Governor Cuomo and the legislature; though de Blasio got funding in a 2014 state budget, Cuomo forced him to provide space to charter schools inside public schools, a humiliation for a mayor who had spent the campaign attacking charters.* Though de Blasio has sometimes claimed credit for ending stop and frisk, a more accurate history is that the practice was winding down at the end of the Bloomberg administration after a court ruled it unconstitutional. He supported an effort to close the jail at Rikers Island that passed the City Council last year, but many derided the plan as not going nearly far enough to reform the criminal justice system.
If you take the view that de Blasio was simply not up to the task of governing New York City, the deeper question then becomes: Why was he able to win that election in the first place? Was this the best Democrats could do? And is there anyone who could do better after he leaves office?
“There's plainly so much appetite in the larger city for something else,” Seigel told me. “We should clearly be able to have better responsible leadership, real police reform, competent schools, all these things and instead we just have this crap.”
Maybe you think that the progressive policies de Blasio has pushed for would not have been taken up by a replacement-level New York Democrat. If the city wouldn't have had universal pre-K or paid sick leave without him, then maybe all the conflicts with the media, the counterproductive efforts to influence national politics, the scandals, and the betrayals of neighborhood activists could be excused.
But that's a hard view to defend now. The last few months have been the toughest of his tenure and he's obviously failed to meet the moment. His police reform plan, released Sunday, is more weakness, guaranteed to be rejected by activists and cops alike.
According to the Times Magazine, he once said that US senators have “the best job on the face of the Earth. All they do is pontificate and travel.” Maybe he would be more at home in a job like that, where he has no responsibility for actually running anything. Not that voters in New York, or anywhere else, would ever put him in the Senate at this point.
The worst part? He's going to be in office until December 31, 2021. That’s going to be a long 570 days, for him and the city both.
Correction 6/10: I mistakenly wrote that de Blasio being forced to provide space to charter schools was a flip-flop. Actually, there was nothing he could have done—while it was a defeat, it wasn’t a reversal on his part. Thanks to Ross Barkan for spotting that.
Thanks for reading What Went Wrong?, a newsletter by Harry Cheadle that publishes every Tuesday. If you have questions or comments, please email me at harrydcheadle@gmail.com. If you enjoyed it, please subscribe and tell someone about it.