Hello, Operator: Can Bill de Blasio Go From Master Strategist to Mister Mayor?

(Photo: Flickr/nycpublicadvocate)

(Photo: Flickr/nycpublicadvocate)

The year: 1980. At stake: the presidency of NYU’s Weinstein Hall dorm.

“It was a hotly, hotly contested race,” Public Advocate Bill de Blasio recalls of his first campaign. His opponent was thwarting his visibility at every turn, ripping down Mr. de Blasio’s posters in the middle of the night.

A disgusted Mr. de Blasio and his team met for an emergency strategy session. “We decided the only thing to do was to have people awake at all hours to replace the posters immediately,” he explained to The Observer last week.

“Our opponents eventually just stopped because they knew they could not defeat our awesome outreach machinery,” he said with a grin. “It was an early lesson in persistence.”

In his all-but-certain mayoral bid, Mr. de Blasio will need equally awesome outreach machinery and at least as much persistence. Even though campaign season doesn’t officially kick off until next year, he currently polls a distant third, in a race fronted by Council Speaker Christine Quinn, with her dominating approval ratings, brimming war chest, and the history-making appeal of potentially being the city’s first female and first openly gay mayor. (Former Comptroller William Thompson typically polls in second place, ahead of Mr. de Blasio and fourth-place contender John Liu, the city’s current comptroller.)

This time around, poster saboteurs will be the least of Mr. de Blasio’s worries as he to attempts to stand out for more than his 6-foot-5 stature. “It’s healthy, it’s healthy,” Mr. de Blasio countered when we brought up his lack of name recognition. “I can tell when I get on the subway, I can tell when I go to the grocery store—it’s evolving all the time.”

In many ways, the mayoral race is a perfect next step for Mr. de Blasio, 51, a savvy tactician who has ascended to a series of local offices using the same political acumen that he deployed in his previous career as a campaign operative for former Mayor David Dinkins, former Senator Hillary Clinton and others.

Mr. de Blasio possesses “real strategic sense and smarts about politics,” said Harold Ickes, a former top aide to President Clinton who picked Mr. de Blasio to manage Ms. Clinton’s 2000 Senate campaign. Mr. Ickes and others recalled how her operation struggled at first, and they credited Mr. de Blasio with turning things around. “Bill’s determination, his personality and values—and not taking himself all that seriously and a sense of humor—won the support of many, many people on the inside,” Mr. Ickes said.

As public advocate, an office he has held since 2010, Mr. de Blasio has found his niche trying to be the chief progressive antagonist to Mayor Michael Bloomberg’s administration. He railed against some of the mayor’s school closures, against the city’s widening economic gap, against the NYPD’s controversial stop-and-frisk tactic, and on down the list. Whenever there is space to Mr. Bloomberg’s left in the public discussion, Mr. de Blasio can be found there, usually holding a press conference.

This has occasionally frustrated Mr. Bloomberg. “He wants to drive everybody out of the city, but that’s okay,” the mayor scoffed, after Mr. de Blasio proposed a tax-the-rich idea in mid-October.

One of Mr. Bloomberg’s top aides, Deputy Mayor Howard Wolfson, characterized Mr. de Blasio as an opportunist. “I think Bill’s made a political calculation that being the antagonist to Bloomberg in the race is his best positioning,” he told The Observer. “He’s been in politics for a very long time as an operative, so I know that he would have thought about that pretty hard.”

Mr. Wolfson, who worked closely with Mr. de Blasio on Ms. Clinton’s senatorial bid, pointed to Mr. Bloomberg’s strong approval rating among Democrats in a Quinnipiac University poll taken in the wake of Hurricane Sandy. Although 55 percent of Republicans disapproved of the mayor, possibly rankled by his in-your-face public-health initiatives, 61 percent of Democrats actually approved.

“I think [Mr. de Blasio] has come to the conclusion that unless you’re criticizing the mayor, you’re not getting a lot of press,” Mr. Wolfson said. “I think he’s made that decision of how to get a lot of oxygen, but I think, ultimately, throwing bricks at the guy who’s at 60 percent among Democrats is not a winning strategy.”