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

FOLLOWING A DORM presidency advocating for improved student life and lower tuition, Mr. de Blasio graduated to a series of jobs in nonprofit groups. He landed on David Dinkins’s mayoral campaign in 1989, as a volunteer coordinator. “I was literally the lowest person on the totem pole. If you go and find the old organizational chart, I was the lowest ranking, lowest paid,” he recalled.

When Mr. Dinkins won, Mr. de Blasio secured a job as a City Hall aide, a four-year position “foundational for everything I’ve done since then,” he said. Not only did Mr. de Blasio acquire a taste for politics, he made a series of instrumental contacts, including another young Dinkins aide named Chirlane McCray, whom he met in 1991 and eventually married.

It was the birth of their first child in 1994 that first gave Mr. de Blasio the idea of running for office on his own, in a roundabout sort of way. It was right after Mr. Dinkins’s loss to Rudy Giuliani, and Mr. de Blasio found himself job-hunting again.

“I had gotten used to the fact that the long-term path I had been on had been fundamentally interrupted, and I was trying to make sense of where to go next,” he remembered. “When you’re about to have a baby, they do this little survey about your conditions at home and one thing and another. The social worker at Methodist Hospital asked about Chirlane, where she worked, one thing and another; then she asked about me, and I said, ‘I’m currently unemployed.’ She started furiously scribbling. I was like, ‘No, wait! It happens a lot in my trade!’”

It would be seven years and even more campaigns before Mr. de Blasio struck out on his own, leaping into a local City Council race in Park Slope. The incumbent councilman had been term-limited out of office, and a crowded field of aspiring politicians emerged to replace him. But with powerful fund-raising connections left over from his operative days, a biography that included work on the local school board and an aggressive door-knocking operation, Mr. de Blasio was able to notch the victory.

Once elected, he put his political mind to work again, climbing the ranks of the City Council and even making an unsuccessful attempt at the speakership in 2005. But by sticking to the progressive topics core to the Democratic electorate, he positioned himself to run for higher office, and in 2009, he set his sights on outgoing Public Advocate Betsy Gotbaum’s job. “It seemed like a natural fit on many levels,” Mr. de Blasio said of the decision, adding that the issues of child welfare and poverty that he worked on while on the Council “clearly fit the purview of the Public Advocate’s Office.”

But it was a hard-fought race for Mr. de Blasio. “He ran against very, very well-qualified opponents,” recalled Ken Sunshine, Mr. de Blasio’s former boss in the Dinkins administration. The field included not only another prominent councilman, but also Mark Green, a former public advocate who characterized the race as “a contest between an effective consumer advocate and a lifelong political insider.” Although Mr. Green led in the public polling, Mr. de Blasio managed to edge him out with a labor-backed coalition that could forage for votes on every block. As Mr. Sunshine phrased it, “Basically, Bill kicked his ass.”

Political insider or not, Mr. de Blasio has gone out of his way to solidify his liberal credentials, regardless of the audience. For example, he presented his plan to tax the city’s wealthiest residents at a Conrad Hotel ballroom filled with, well, some of the city’s wealthiest residents. “Now, some of you may be thinking that this is an interesting place to come and make this proposal,” Mr. de Blasio mused. “You might say, ‘You have come to the lion’s den.’” He pivoted: “Well, I think it’s a room full of people who care about New York City.”

Just last week, Mr. de Blasio threw himself to the so-called lions again at a pro-business forum hosted by Crain’s New York Business at the Sheraton, using the very first question to tout his tax proposal.

The plan, which would generate $532 million per year in revenue from those making $500,000 or more, has become a key part of Mr. de Blasio’s agenda. And the program the tax hike would fund? Why, it would be for universal early education, which happens to be a top priority of Mr. de Blasio’s top opponent for next year, City Council Speaker Christine Quinn.

Education is hardly the sole issue on which Mr. de Blasio has sought to outflank Ms. Quinn. Before Sandy blew away politics as usual, Mr. de Blasio could be found spending his Sundays at African-American churches in Central Brooklyn and southeastern Queens, harping on Ms. Quinn for blocking paid sick day legislation in her chamber.

At a mid-October appearance at a Bed-Stuy church, Mr. de Blasio took swipes at both Mr. Bloomberg and Ms. Quinn for their stance on paid sick days. “The mayor—this may shock you—the mayor doesn’t think we need paid sick leave days. Apparently, for him, it’s not something he feels he needs. Maybe the same people he hangs out with don’t feel they need it. But over a million New Yorkers do. We have to tell the mayor, we have to tell the City Council, we especially have to tell Speaker Quinn in the City Council, who will not bring this to a vote: ‘It’s time to bring this to a vote.’”

Mr. de Blasio, whose wife is African-American and an unpaid adviser to his campaign, even attempted some corny church-related humor that the crowd actually seemed to appreciate.

“As a public servant, it would only be my obligation to report a situation like this, because I would have to call the fire department, because the choir is on fire!” he joked to open his speech. “But maybe it’s not necessary to call the fire department, because of the cool, smooth stylings of the band!”

While he naturally hopes to make inroads with black voters, his campaign plan, as multiple aides described it, is aggressively focused on the outer boroughs, which are home to 80 percent of the city’s population but have produced very few of the city’s mayors.