It is not hard to imagine that four years ago, if a few thousand Iowans had decided to vote for Hillary Rodham Clinton instead of Barack Obama, Howard Wolfson would now be at the front podium of the White House briefing room, whacking the Washington press corps for their supposed slights against President Clinton, or flying around the world on Air Force One, given a seat in a sweet spot near the Leader of the Free World, whispering into her ear about the political and historical ramifications of whatever crisis of the moment was unfolding.
But instead, a few days before Thanksgiving, Mr. Wolfson crowded into a second floor meeting room in City Hall to brief a dozen or so reporters about the latest news in the Bloomberg administration’s ongoing struggle with protesters down at Zuccotti Park. The ostensible purpose of the impromptu press scrum was for Mr. Wolfson, whose official title is deputy mayor for government affairs and communications, to brief the press on preparations the city was undergoing to prepare for what Occupy Wall Street described as a “Day of Action,” a massive nationwide protest to galvanize the movement. As anyone who saw him on the trail when he was shilling for Ms. Clinton during her bruising 1999 run for U.S. Senate, or during her even more bruising 2008 run for president, or any of his side gigs for Fox News or the 2004 John Kerry campaign, it was vintage Wolfson. He said that tens of thousands of protesters were going to descend on the city, thus making anything less seem like a disappointing showing for the Occupiers. He rerouted questions about the administration’s raid on Zuccotti Park a few days prior into a discussion about the unwillingness of Mayor Bloomberg’s chief critics to take a definitive stand on the raid, holding up for ridicule some of the more outrageous statements they had made.
(“It always astonishes me,” said Hugo Lindgren, the editor of The New York Times Magazine and a friend of Mr. Wolfson’s since his student days at Duke. “He has the ability to seem natural and conversational and somehow stay right on message.”)
During the raid, one city councilman, Ydanis Rodriguez, had been arrested and detained for 17 hours. Before Mr. Wolfson met the press, Mr. Rodriguez held a press conference of his own, in which he showed off cuts on his face from the police and alleged that he was targeted due to his stature as an elected official and outspoken critic of the Bloomberg administration.
When Mr. Wolfson was asked about the allegations, he looked confused for a moment.
“Wait. Are you saying he is saying he was particularly singled out because he was a councilman?” he replied, nodding to himself, as if he were trying to wrap his head around an idea—that a city official would be given special treatment of a punitive sort—so preposterously outside the realm of possibility that it tested the ability of human mind to logically progress from one thought to the next.
Yes, instead of state dinners and nuclear codes and facing down the Great Recession and the Tea Party, Howard Wolfson is here, attending late-night community meetings in Queens, wrangling over budget items with members of the City Council, and batting clean-up for Mayor Mike Bloomberg.
A few years ago, when Mr. Wolfson was considered one of the leading Democratic strategists in the nation, he seemed destined to settle in for the kind of easy life that a television pundit enjoys, or as a high-powered Democratic lobbyist.
Now, he is a bureaucrat. It’s as if Karl Rove had left the White House to go work for the Dallas Water Utilities, or James Carville eschewed his regular rounds on Crossfire or Meet the Press after successfully steering the 1992 Bill Clinton campaign, and served as a spokesman for the mayor of Baton Rouge.
“I don’t consider myself in that league,” Mr. Wolfson said in an interview last week. “I have never won a presidential campaign.”
This is true, but that may be due more to Mr. Wolfson’s having been tasked with making the case for a campaign that has come to be remembered for one of the biggest implosions in political history than to anything Mr. Wolfson failed to do. Back then, Mr. Wolfson had become one of the chief antagonists of then-candidate Obama, fielding daily conference calls with hundreds of reporters at a time. Former campaign officials recall him as the last man in the foxhole, the one who kept on fighting, kept on attacking, kept on getting into the office earlier and earlier even as the rest of the staff began angling for jobs in a future Obama White House.
The decision to come to City Hall, Mr. Wolfson says grew out of the ashes of that campaign.
“My goal was to go to the White House,” he said. “If Hillary Clinton had won the presidency, my goal was to go into government. I was not going to go back into the private sector. I had my heart set on returning to government. You play a certain role in a campaign that you are really invested and believe in, and why not go into government and continue to try and achieve some of the outcomes that you were promising during the campaign?”
Bloomberg insiders, many of whom had been with the mayor since he first ran for office in 2001, were skeptical of Mr. Wolfson, knowing that he came out of an environment that seemed to epitomize political dysfunction. Eventually, he took over Kevin Sheekey’s role as City Hall’s political director, but his portfolio has broadened and turned wonkier over time, encompassing budget and land use and education policy negotiations with lawmakers here and in the city.
“I think that what is interesting about Howard is that he came in with heavy-duty political experience, and made the transition fairly quickly and very seriously to a real governing role in a way that was more than anybody, including himself, expected,” said Micah Lasher, the Bloomberg administration’s chief Albany strategist.
Those inside and outside the administration say that they have noticed a distinct shift of emphasis as Mr. Wolfson has grown into the role formerly occupied by Mr. Sheekey. Whereas Mr. Sheekey—who is now at Bloomberg LP—was consumed with the dark arts of politics, staying just out of reach of reporters and coming up with dozens of complicated schemes at a time (or at least creating the illusion that he was), Mr. Wolfson has run the political side of City Hall like a political campaign: problems come up, solve them. Stay on message. Stay on offense. Keep your allies close. Avoid needless political cat fights.
It is Mr. Wolfson who has tried to dial down some of the rhetoric with Albany. It was he who advised that the administration pause after uproar over its new homeless policy. When the City Council hauled administration officials before them after the blizzard snafu, Mr. Wolfson took over and ran point with the media (he was on vacation during the blizzard itself, and so could only look on and cringe when the mayor made his famous suggestion that snowed-in New Yorkers go see a Broadway play).
“He has given a political sense to an administration that has often lacked a political touch,” said one local official who is often an administration antagonist.
The third term has been (to put it mildly) a rocky one, and Mr. Wolfson has often been called to specific projects when they seem to be going off the rails. When a lack of public support threatened to derail the city’s bike lane expansion, Mr. Wolfson took over the message, answering critics point-by-point, and strapping on a helmet and spandex to become the city’s cycler in chief.
“It was not a surprise to anybody that it was a difficult winter with the press on the bike lanes. He came up with ways to answer the questions point by point that were made by reporters, and that strategy was really effective,” said Janette Sadik-Khan, the commissioner of the Department of Transportation, adding “You are seeing a leaner, meaner Howard Wolfson because of the bike lanes.” (Mr. Wolfson lost 25 pounds after taking to his bike.)
“I was tired of our commissioner getting misrepresented, and I was tired of other people having their day in the papers,” Mr. Wolfson said. “So I said, ‘We are fighting back.’ This is going to be an ongoing struggle, but if you look at the polling, this issue is absolutely headed our way.”
Then, Mr. Wolfson took to Twitter to answer criticisms directly and to engage with like-minded supporters. It is a technique that has now infused the entire press office at City Hall, which has taken to the social media platform to rebut stories it disagrees with, often retweeting a negative headline with the simple words, “Not True.”
His influence around City Hall has been felt in other ways as well, administration officials say. Mr. Wolfson has been one of the driving forces behind the mayor’s so-called “Freedom Agenda,” in which Mr. Bloomberg lines up solidly behind the Ground Zero Mosque, the Chinese dissident artist Ai Weiwei and even the free speech rights of the kids in Zuccotti, and he has had a heavy hand in some of the mayor’s more elevated rhetoric in the service of that agenda. He guided the mayor on his political endorsements last year, in which Mr. Bloomberg spread his money and his support to a handful of socially liberal fiscal conservatives in both parties.
When Mr. Wolfson took the job inside City Hall, the widespread assumption among political observers was that it meant something big was in the offing for the future of Mike Bloomberg—if not a presidential run then something equally as big. Why else, after all, would a political superstar come here?
Because he wanted to, Mr. Wolfson said. “I was coming here to do the job of deputy mayor for government affairs and communications. I was not aware that we were launching the Apollo Project.”
Still, politicos, especially those lining up in opposition to Mr. Bloomberg, wonder if Mr. Wolfson won’t jump ship for some kind of national-level job in advance of the 2012 elections. The press, they say, is already cowed by him (“There is this mythology that surrounds him,” said one rival flack. “He has to defend some pretty indefensible positions, and the press takes him at his word.”) The third term, they say, is a lost cause. How much longer can Mr. Wolfson want to be spend time holding the bag?
His job now, he says, is to get the mayor simply to build the platform so that his words get amplified, no easy task after a decade in the mayoralty. The mayor has been in many respects far less visible than he was during his first two terms, cutting down on the number of daily press conferences, and preferring instead major speeches in hand-picked venues on themes of national import.
“Like the president, the mayor, I don’t believe, should be overexposed. I think you have to pick your spots,” he said, adding, “You don’t really tell Mike Bloomberg what to say. But you can, in my position, attempt to advise him on the best venue, the best way to say what he wants to say … You make a decision to clear Zuccotti Park. How do you explain that to the people of the city?”
That job, of course, fell almost as much to Mr. Wolfson as it did to Mr. Bloomberg. The day after the press scrum in City Hall, he did the local Fox affiliate and then headed down to CNN. There the host asked about reports that members of the media were targeted during the raid on Zuccotti.
Mr. Wolfson went back to slamming the critics of the mayor for the hyperbolic statements they made in response to the raid.
Back at City Hall, he disputed the notion that the action had made the municipal problem of Occupy Wall Street worse.
“I don’t think it’s intractable. We should go to Zuccotti Park,” he said, confident the sight of the cleared plaza would prove his point.
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