Before he called a meeting of the City Council's special events committee to order on December 6, Walter Burnett Jr., the chairman, imparted a piece of political insight to his embattled colleague Nicholas Sposato.

"I keep telling you, there's a black caucus, a Hispanic caucus, and a white-haired caucus," said Burnett, the 27th Ward alderman. "But you need to get a little grayer before you can go there."

Sposato chuckled, though he didn't find the topic terribly funny. A former fireman, Sposato won his seat last year in an upset over a favored political insider, and his ward, the 36th, would be dramatically redrawn under proposed new boundaries—a sign that the rookie was on the shit list of the veteran white guys overseeing the decennial remap.

But the comment revealed even more about Burnett's mischievous sense of humor, shrewd understanding of how the city operates, and confidence about his own prospects based on years of loyalty to his patrons. In fact, anyone who really wants to understand how Chicago works should take a close look at Walter Burnett. Ward boundaries may shift around him, but he's virtually unmovable.

Burnett is easy to underestimate. Apart from the figure he cuts—he's a compact 5-6, wears brainy wire-rimmed glasses, and, when he can ditch the suit, favors the leather-jacket-and-turtleneck ensemble of an early 70s Donny Hathaway—Burnett often seems part of the indistinguishable mass of Chicago aldermen who go along with whatever the mayor wants, whichever mayor is in office. His voting record is full of "aye" votes, including on such pivotal matters as the widely loathed parking meter deal, tax increment financing handouts to Fortune 500 companies, and city budgets that have drained reserves, raised taxes, and cut services. Not only does he refrain from criticizing the mayor, he often joins his council colleagues in extended public ass kissings, while insisting that he spars with the administration behind closed doors.

Burnett grew up in public housing and served time in prison before getting into politics, and when he does speak up, he often comes across as unpolished, unscripted, and unsophisticated—an entertaining but lightweight elected official who follows orders so he can enjoy the comforts of political incumbency. In 2009 Burnett famously compared voting for the meter deal to taking a dose of erectile dysfunction medication, since, he said, it sounded great but could have lots of unforeseen side effects. Despite the spot-on analysis, Burnett voted to approve the deal anyway because former mayor Richard M. Daley wanted it done. Yet during Daley's final council meeting last May, Burnett effusively thanked the mayor. "You taught me how to be independent," he said.

But Burnett is a keen observer who uses the lowered expectations as cover. Even before Daley left office, the alderman went to work figuring out the new mayor. "Rahm, man, he is a powerful dude at this point," Burnett says. "And I see how he do it with the media. You ask him a question, he'll make a joke and try to check you on it. Like it's a joke, but he's saying, 'Why did you ask me that question?'

"What I do with him, the same thing I did with Mayor Daley—I pray for him. And it always works."

Last fall Burnett took me on a tour of his ward, one of the craggiest and loopiest in the city, stretching from gentrifying areas around the Loop to struggling communities in the heart of the west side. Our drive became a tour not just of the ward, but of a childhood and career shaped by political power plays dating back to the days of the Democratic machine.

Our first stop was on Division just east of Halsted, next to an empty lot that was once the site of a Cabrini-Green high-rise. "I lived over there as a kid," he said.

Burnett was born in Cook County Hospital in 1963, when his father was 21 and his mother was a teenager. Walter Sr. worked in a west-side grocery store and the family lived in the Rockwell Gardens public housing complex before moving to Cabrini-Green, first in the high-rise on Division and later in a row house a couple blocks away.

Though Cabrini became infamous for violence, Burnett has fond memories of growing up there. "People looked out for each other," he says. "We would get salt and sugar and cereal from our neighbors. If we didn't have clothes, we'd get their hand-me-downs."