Critics say Bill de Blasio's presidential aspirations are delusional. Can he prove them wrong?

Hunter Walker
White House Correspondent
New York City Mayor Bill de Blasio speaks at the 2019 American Israel Public Affairs Committee policy conference in March. (Photo: Jose Luis Magana/AP)

The line between visionary and madman is a thin one. New York City Mayor Bill de Blasio has been walking on that delicate tightrope for months as he has flirted with launching a presidential campaign.

The mayor has been saying he will make his final decision this month, but he has a slim chance of victory, and political observers and local officials are confused by his strategy. One of the city’s top Democratic operatives echoed conventional wisdom when asked about a potential de Blasio presidential bid.

“I have no idea what the mayor is doing,” the operative said. “And I really don't think he does either.”

In this sea of doubters, de Blasio’s closest allies and advisers believe their man is a misunderstood hero. They argue his policy record is underappreciated and point to his history of underdog triumphs as signs that de Blasio could pull off a truly incredible upset.

Peter Ragone, a longtime adviser and friend of de Blasio’s, cited the shocking 2013 victory that brought him to City Hall as proof “the pundit class” has the mayor wrong.

"Every single time he has run for office he has been maligned by insiders and the media. And then what happens? He sweeps swaths of the electorate,” Ragone said. “Why is it he is always told he has no shot, yet he wins elections [by] landslides?"

There are two dramatically different views of the mayor’s presidential ambitions. As de Blasio faces daunting poll numbers and a staff exodus, the critics see his fixation on the White House as either a means to a different end or the product of a politician with a dwindling team and drunk on hubris. But those in his inner circle see a true believer who has delivered on a sweeping progressive vision despite opposition from New York’s political class, particularly its infamously aggressive press corps. In the minds of the mayor and his associates, he should not be counted out.

As reports of an imminent de Blasio presidential announcement spread in recent days, Yahoo News spoke to over a dozen political leaders, experts and strategists in the Big Apple, including some who have worked for de Blasio. One word kept coming up in conversation after conversation about the mayor’s ambitions — “delusional.”

“I think the city is mostly baffled by this. He's been an average mayor at best,” the Democratic operative said.

“I think this is one of the most delusional people who have ever inhabited City Hall, and I seriously mean that,” said Gerson Borrero, a political commentator who has spent decades as a regular on multiple New York television and radio stations.

Nick Rizzo, a Democratic district leader in Brooklyn, said local politicos are scratching their heads trying to imagine de Blasio’s rationale. “He still has smart people working for him, but he seems really disconnected from reality,” Rizzo said of de Blasio.

Indeed, De Blasio’s poll numbers are bleak and show it’s not just the city’s political establishment that’s not eager to see him launch a presidential campaign. A Quinnipiac University survey released last month showed de Blasio had an “anemic” 42 to 44 percent approval rating with over three-quarters of New Yorkers saying they didn’t want the mayor to launch a White House bid.

Outside of the Big Apple, de Blasio’s numbers are even worse. A CNN poll released late last month found de Blasio dead last in the crowded Democratic field with none of the party’s registered voters or Democratic-leaning independents giving him their support. That same survey found just one percent of Democratic voters wanted to hear more about de Blasio. A Monmouth University poll from last month showed de Blasio near the back of the pack with just one percent of Democrats saying he’d have their vote. In March, Monmouth conducted a poll that looked at voter opinion of the primary field and found de Blasio was the “only name among 23 candidates or potential candidates who have been tested in Monmouth’s polling this year to earn a net negative rating among Democrats.”

Bill de Blasio with his his wife, Chirlane McCray, at an election-night victory gathering. (Photo: Julie Jacobson/AP)

The unlikeliness of a de Blasio win has many in the city speculating that his presidential flirtation is a scheme designed to accomplish some other goal. One staffer for a top state official suggested that he may be angling for a position with the much more high-profile progressive candidate Sen. Bernie Sanders, I-Vt. Another theory raised by multiple local operatives and a former confidant of the mayor is that de Blasio is trying to increase his profile to position his wife, Chirlane McCray, for a run for a congressional seat or the borough president’s office in Brooklyn once his term is through.

But those who know de Blasio insist he would not be eyeing the presidential race for any ulterior motive. De Blasio’s early political career took off with stints as a strategist in New York including managing Hillary Clinton’s successful U.S. Senate campaign in 2000. De Blasio has long viewed himself as a savvy operator and relishes hitting the campaign trail.

“He’s a competitive guy. And if he decides to run, it’ll be because he actually thinks he can win,” a former de Blasio adviser said.

The world may not see a path to victory for de Blasio, but those who know him are certain he must believe he has a chance — even if they don’t understand his thinking. And whether or not they see what de Blasio sees, some who have worked with him say he should be taken seriously.

“I think you would be foolish to underestimate de Blasio,” said Rebecca Katz, a former aide to the mayor and founder of New Deal Strategies. “I don’t see why he is running, but now that he is running, this is Bill de Blasio at his best, campaign Bill de Blasio.”

In many ways, de Blasio’s initial 2013 mayoral victory was a precursor to the progressive wave that reshaped Congress last year and has made Sanders one of the frontrunners for the Democratic nomination. De Blasio won after casting New York as a “tale of two cities” plagued by inequities he vowed to address.

One former de Blasio staffer said the mayor may feel he belongs in the presidential race because of his work bringing progressive populism into the conversation. However, they also suggested the left wing of the Democratic Party has since moved beyond de Blasio.

“He was at a certain point the main person in the nation talking about income inequality. And he was right. Now Bernie and [Elizabeth] Warren are talking about the one percent,” the former staffer said, adding, “So, he’s not the only one anymore. And, especially if you’re a progressive, if you’re a white man you better be bringing something special to the table. He’s not. There are better messengers than him.”

Bill de Blasio testifies during a joint legislative budget hearing on local government in Albany, N.Y., in February. (Photo: Hans Pennink/AP)

As mayor, he has some signature achievements that his allies say shows he delivered on this pioneering progressive agenda. Most prominently, de Blasio established universal pre-kindergarten, a paid sick leave program for city workers, enacted a $15 dollar per hour minimum wage, and presided over a steady drop in the violent crime rate while curbing the New York City Police Department’s controversial “stop and frisk” program.

A city council member told Yahoo News they believed de Blasio could make an “important contribution” to the presidential race if the mayor throws his hat into the ring. Along with the aforementioned policies, the council member cited de Blasio’s expansion of affordable housing and after-school programs.

“Mayor de Blasio has done a good job when it came to investing in important areas for New Yorkers, especially those who are part of the working class,” the council member said.

While de Blasio has scored some notches on his progressive belt, some of his opponents point to persistent issues in New York to argue the mayor hasn’t lived up to his promise to unite the “two cities.” Gerson Borrero, the political commentator, pointed to rising rents, the dismal state of the city subway system, and stark racial divides in the neighborhoods and public schools to question de Blasio’s progressive bonafides.

“As we say in Spanish, ‘De la boca pa’ fuera,’” Borrero said, which roughly translates as “from the mouth, out.” “He barks, but when he bites, it’s toothless.”

De Blasio and his allies acknowledge the sad state of the city’s public transportation system, but say blame ultimately lies with Gov. Andrew Cuomo, who is in charge of the state transit authority that runs the city’s subways. Borrero doesn’t buy that and says de Blasio should have done more to challenge the governor.

“If these were things where he really did something or put up a fight he could run on them,” Borrero said.

New York Gov. Andrew Cuomo, center, and Bill de Blasio arrive for a news conference outside the Port Authority Bus Terminal in New York City. (Photo: Mark Lennihan/AP)

But Ragone, the mayor’s friend and longtime adviser, believes de Blasio has a stellar record that has gone unnoticed due to unfair media coverage. "One of the reasons he's not viewed as a viable candidate is the national media has only seen terrible stories about the guy for six years, despite a pretty impressive record,” he said. “The national media and voters will make their decisions about his viability, but it's probably not going to be done through the lens of the New York City press corps, and I think that's going to be a different conversation.”

De Blasio’s contentious relationship with City Hall’s “Room 9” press corps was highlighted when he was implicated in the death of a groundhog.

In February 2014, a month after he took office, de Blasio went to the Staten Island Zoo to participate in the Groundhog Day ceremonies. Before the animal known as Staten Island Chuck made his annual meteorological prediction, de Blasio held up the rodent to the crowd. But the groundhog squirmed uncomfortably, and de Blasio dropped him on the ground as onlookers screamed. The New York Post later revealed that the rodent died “a week later,” and “zoo officials went to great lengths to hide the death from the public.” The conservative tabloid dramatically declared that the mayor “has groundhog blood on his hands!”

Staten Island Chuck’s death was both covered extensively and mocked relentlessly on Twitter. The incident was one of a series of idiosyncratic moments in de Blasio’s tenure that became recurring themes in reporters’ coverage and social media posts, which included the time the mayor ate pizza with a fork, his penchant for running late and his habit of regularly making an over-11-mile round trip on weekdays to work out at a gym in his old Brooklyn neighborhood.

Staten Island Chuck (Photo: Andrew Burton/Getty Images)

But New York’s muckrakers have also exposed serious issues with de Blasio’s administration. Investigations have questioned how much de Blasio really did to end “stop and frisk,” documented how much time he spends out of the officeexposed unflattering emails written by senior officials, detailed the firing of the city’s top watchdog, and chronicled a bribery scandal involving one of the mayor’s donors.

De Blasio’s frustration with the media has manifested itself in a tendency to hold fewer press conferences than his predecessor, Michael Bloomberg. Members of the press corps complain that he is inaccessible, and in some of the availabilities he has held, de Blasio has snipped at the assembled reporters. Private emails between de Blasio and top aides that were exposed due to a legal battle waged by the New York Post and local TV channel NY1 show the mayor fuming that the media is “pitiful” and biased against him. One former de Blasio consultant described the situation as “toxic.”

Rebecca Katz, the mayor’s former aide, said de Blasio’s reluctance to engage the media hurt him.

"The most maddening part of all this is that some really amazing stuff has happened and he's been unable to take credit for it. I think universal free school lunch is a huge achievement, but the Mayor didn't even go the press conference announcing it,” Katz said. “Every single kid in New York City can have free school lunch with no stigma, and that's because of the de Blasio administration. But does anyone know that?"

The Democratic operative pointed out that the tension could have real consequences if de Blasio runs for president since Room 9 was home to many reporters who went on to national outlets. “The Mayor has never done a good job of working with the press the past few years — and the number of reporters who graduate from City Hall to cover national issues is going to do him no favors,” the operative said of a potential presidential bid.

This is a lot of baggage to carry into an already improbable campaign, and as he faces these challenges, de Blasio has something of a skeleton crew at his side. Many in the mayor’s orbit have clearly not been willing to come along for the 2020 ride even as multiple sources say de Blasio has put out “feelers” trying to get old staff members on board. Katz was a top aide to former Sen. Harry Reid, D-Nev., before working on de Blasio’s 2013 mayoral campaign and joining his administration. She departed in 2015 and told Yahoo News she made the decision “because it felt like the right time to leave on both a personal and professional level.”

De Blasio’s allies point to his stunning upset win in 2013 as evidence he shouldn’t be counted out. However, that victory was accomplished with the help of topflight political operatives, almost all of whom have left the mayor’s team.

Along with Katz, the staff that helped de Blasio get to City Hall included John Del Cecato, who made commercials for both of President Barack Obama’s successful White House bids. Del Cecato crafted an ad that highlighted de Blasio’s interracial family and was a crucial part of his eventual win. De Blasio’s 2013 campaign also included Lis Smith. Since parting ways with de Blasio, Smith joined the team of another mayor, South Bend, Indiana’s Pete Buttigieg. Smith took Buttigieg exactly where de Blasio hopes to go — from a longshot to a plausible 2020 presidential contender. Bill Hyers, another Obama veteran who has gone on to run his own consulting firm, managed de Blasio’s 2013 mayoral campaign. Del Cecato, Smith, and Hyers are all no longer working for de Blasio and did not respond to requests for comment on this story.

New York City Mayor Bill de Blasio testifies during a joint legislative budget hearing on local government Monday, Feb. 11, 2019, in Albany, N.Y. (AP Photo/Hans Pennink)

One ex-de Blasio campaign aide suggested the number of departures is because the mayor is “a grueling person to work for.” They described de Blasio as “extremely particular” and suggested his tendency to get angry and fixated on minutiae might be a factor in the “lack of interest” his former staff has in joining a potential presidential campaign even though they might think he has “important things to say” in the race.

“If they don’t think he has a chance to win, why would they go through it?” the former aide asked. “It’s one thing to deal with that kind of personality when you can have an impact. It’s another thing to endure it for a longshot campaign.”

And it’s not just the 2013 campaign team that won’t be on board if de Blasio enters the presidential race. Emma Wolfe, de Blasio’s chief of staff, is almost universally well-regarded among New York City politicos and has been described as the mayor’s “most trusted aide.” According to multiple sources, Wolfe will not be joining de Blasio’s campaign team. Wolfe did not respond to a request for comment.

The lack of participation from some of the mayor’s staffers has fueled the conventional wisdom among New York’s political establishment that the potential campaign is a fool’s errand. One city council member told Yahoo News they asked a senior staffer from de Blasio’s administration why they weren’t working on his campaign team.

“Their response was just a blank stare,” the council member said.

Multiple top City Hall aides have left the administration entirely in de Blasio’s second term, which began in 2018. Mike Casca, who worked on Bernie Sanders’s 2016 presidential campaign, went on to serve as de Blasio’s City Hall communications director. In April, Casca left the administration to work on Fairness PAC, de Blasio’s political operation. Casca seemed a natural fit to take a role on a presidential campaign if de Blasio decided to launch one, but he departed the PAC and administration last Friday amid reports the mayor was set to officially enter the race this week. Casca declined to comment on his reasons for leaving de Blasio’s team or his plans for the future.

Ragone rejected the idea de Blasio has experienced unusual turnover.

"It's year six of an administration. ... I've been there myself. People do leave. That to me is not that surprising,” he said.

But the exodus has unquestionably left de Blasio with a lean and relatively low-profile political staff as he eyes the White House.

In an interview on the local channel NY1 Monday night, de Blasio addressed a spate of reports he planned to kick off a presidential campaign on Wednesday. The mayor said he is still deciding whether to run and will not make any announcement this week.

As de Blasio weighs a formal bid for the White House, multiple sources told Yahoo News his political operation is being led by Jon Paul Lupo, a former official in his administration who left City Hall to join Fairness PAC. Prior to working for de Blasio, Lupo was chief of staff to former Brooklyn Borough President Marty Markowitz. Before joining Markowitz’s team in 2011, Lupo worked on House and Senate campaigns for Democrats Tim Johnson and Jim Webb. Sources also told Yahoo News that Jim Crounse, a longtime de Blasio ally who worked on the 2013 race and specializes in direct mail campaigns, will have a role on the mayor’s team if he pulls the trigger and enters the presidential race.

Lupo, who declined to comment on the record, has a solid reputation in New York City political circles. Katz described him as a “very smart and capable individual.” But one local Democratic operative who knows Lupo and holds him in high esteem said they were nevertheless confused to see him taking a senior role in de Blasio’s campaign-in-waiting, given its lack of support.

“I really want to know what’s up because he’s smart. He’s like a legitimately smart guy,” the operative said of Lupo, adding, “So, I want to know who’s blowing smoke up whose ass.”

Yet those who know de Blasio say the mayor hasn’t made a final decision yet, and his choice clearly doesn’t seem to be based on poll numbers or public perception.

“He has always been counted out, and he has always beaten expectations,” the former adviser said of de Blasio. “So he’s listening to his heart and not his head.”

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