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.)
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