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.