Less than three months before he leaves office, Mayor de Blasio is reportedly planning to run for Governor, despite doubts expressed by some of his political advisers, flagging support among even the unions that still support him and his proven lack of popularity outside the five boroughs.
But while some political experts say the Mayor entering a Democratic primary that could include State Attorney General Letitia James and Public Advocate Jumaane Williams would take away support from both of them and make it easier for Governor Hochul to capture the party's nomination, one political consultant who's not a fan believes he's not a hopeless long shot.
All About the Base
"It would make sense for him to do it in a crowded field," said Hank Sheinkopf, whose first experience in a political campaign came as a teenage volunteer for Herman Badillo's unsuccessful run for Mayor in 1969, and has worked with unions ranging from Teamsters Local 237 to a police coalition that sought the rollback of recent city and state criminal-justice reforms they say have complicated their members' jobs.
He explained that Mr. de Blasio "has an unmovable 32, 33 percent of the vote. No matter what he does, no matter how many homeless people there are or dead people on the streets in The Bronx, he holds on to those voters."
Mr. Sheinkopf said the Mayor has continuously drawn his strength from two voting blocs—progressives and black residents—who are the core of Mr. Williams's support as well, and to a large degree, Ms. James's.
"He's probably the worst thing that could happen to Jumaane Williams," he continued. "He certainly doesn't help Tish James—certainly in Brooklyn and the black community."
Mr. Williams a week earlier formed an exploratory committee to consider a challenge to Ms. Hochul, whom he lost to by 6 points in 2018 in the Democratic primary for Lieutenant Governor, when she benefited from having the strong support of then-Gov. Andrew Cuomo. The day after his announcement, Ms. James hinted she might forsake what would appear to be an easy bid for re-election to run for Governor as well.
Just a Spoiler?
There are some political pros who write off Mr. de Blasio as at best a spoiler who could cost Mr. Williams or Ms. James the party's nomination. One strategist, who spoke conditioned on anonymity, said his entering the race "wouldn't affect things that much. There are some unions that are loyal to him; that might take them off the playing field. There is a small contingent of black people that are still de Blasio followers."
But Mr. Sheinkopf insisted that the Mayor's base was solid enough to make him formidable if Ms. James and Mr. Williams both ran and diluted each other's support as well. "In a crowded field, anyone can win," he said.
He argued that Mr. de Blasio's "real skill is not being Mayor, it's being a political consultant. And the source of his success his entire career—his understanding of black life, sensitivity to the black community—makes him a player."
One other thing that the Mayor understood, Mr. Sheinkopf said, was "there's a demographic shift going on in the city that benefits him: less gender-based, less race-based, more ideological." He said Mr. de Blasio could tap into the same kind of progressive voters who gave the then-unknown Alexandria Ocasio-Cortez her stunning congressional win three years ago.
Having It Both Ways
There have been some on the left, particularly those aligned with the Democratic Socialists of America, who have called Mr. de Blasio a sellout going back to his rebuffing their demand in June 2020 to cut the Police Department budget in half, instead reducing the NYPD's $6-billion allocation by only $1 billion.
But, alluding to counter-actions by the Mayor, such as his two weeks later signing a bill that subjected police officers to criminal charges if, while making an arrest, they compressed the diaphragm of a person with whom they were struggling, Mr. Sheinkopf said, "The genius of Bill de Blasio is that for years he played it on both sides and got away with it."
But even as the Mayor earlier in the week pointed to his success in using a vaccine mandate in the public schools to get many of the longtime holdouts employed by the Department of Education inoculated to avoid being suspended without pay, and a fourth consecutive month of crime dropping, problems in other agencies under his control continued to fester. They included chaos in the city jails system, a growing problem involving assaults of juvenile-detention workers by teenage detainees, and racial strife in the firefighter ranks that was the subject of a front-page New York Times story Oct. 2 disclosing the suspension of nine firefighters who had mocked George Floyd's death.
Mr. Sheinkopf said Mr. de Blasio's inability to manage many key components of city government might not even be the biggest hurdle for him to surmount if he captured the Democratic nomination. He said, "It's hard to see how he functions as a Governor considering his relationship with people in the suburbs and upstate over the years," where Republican candidates have sometimes targeted their campaigns not on highlighting their opponents' flaws but by tying them to the Mayor.
"He will be a reminder of what a lot of people in the suburbs and in western and northern New York are worried about," Mr. Sheinkopf said.
May Not Have to Worry
"Can he win a general election?" he asked, then answered: "Lee Zeldin will beat him to death."
A more-likely scenario, he said, was that the Mayor, Ms. James and Mr. Williams, whether as a duo or if all three ran, would siphon enough votes to add to Ms. Hochul's advantages as an incumbent, even though by next June's primary, she will have been in the job for only 10 months.
"In all probability, she is victorious," he said. "And unlike everybody else, she is the Governor."
Another veteran strategist, Maureen Connelly, who helped guide both Ed Koch and Michael Bloomberg to their initial victories as Mayor that propelled each to three terms in that job, said Mr. de Blasio's political skills could not cover up his weaknesses as an executive.
"He has been a failure as Mayor," she said. "I don't know how much of his black support is still there—the crime rate is out of control and most of the victims are black."
She conceded he has seemed more energized since the pandemic, spending his mornings fielding questions from the media in a tightly controlled format rather than spending the time working out at the Park Slope YMCA.
But Ms. Connelly said Mr. de Blasio displayed similar enthusiasm during his last run for office, adding, "I think this campaign will be like his presidential campaign—a mirror image. He's fiddling while New York City burns."
And, she said of Governor Hochul, "She's been doing a pretty good job."