Politics in Uptown boils down to one woman: Helen Shiller, the long-serving alderman of the 46th Ward. And depending on your position on the political spectrum you either love her or hate her.

Personally I don’t understand why she stirs up so much passion. Shiller’s basically a pleasant person who oversees an effective ward service operation and is committed to liberal causes–like gay rights and gun control–that generally go over big on the lakefront. Her critics say she’s keeping Uptown a slum by making it hard for developers to put up their projects, but with real estate prices rising and buildings going condo left and right–as Harold Henderson points out elsewhere in this issue, the percentage of lots occupied by condos increased by 102 percent in the 90s–it’s hard to buy their case.

At the risk of generating dozens of screechy e-mails, I think it all comes down to good old-fashioned class warfare. Shiller’s made it clear there will always be a place for the poor in Uptown and some people can’t abide that. She says her cause is justice; her foes say she keeps the poor in Uptown so she can control their votes. “Shiller’s main motive was that she was building a political power base which included as many winos as she could drag to the voting booth,” columnist Mike Royko once wrote.

Funny, but not really fair: in a city notorious for its corruption, neither Shiller nor anyone in her organization has ever been indicted, much less convicted, for the sort of illegal electioneering alluded to by Royko. She’s not a lawyer; she doesn’t run an insurance or real estate business on the side. Clearly she’s not in politics to make money, although it looks as though her son, Brendan Shiller, is carrying on that great Chicago tradition in which the relatives of powerful politicians become zoning lawyers.

Some of the animosity against her is a remnant of the culture wars of the 1960s and 1970s. Born and raised in New York City and educated at the University of Wisconsin in Madison, Shiller came to Uptown in the early 70s as part of a vanguard of shaggy-haired radicals looking to change the world. Within a few years she and her comrades had created the Heart of Uptown Coalition, which oversaw health and legal clinics, distributed clothes and meals to the poor, and freaked out older white residents by aligning itself with the Black Panthers. In 1977 the group officially moved into local politics by running Shiller for alderman. In those days the ward was controlled by hard-nosed Democratic operatives who’d started in politics under the first Mayor Daley and were not about to let this crowd take over without a fight. She lost by 1,000 votes.

I’ve witnessed eight 46th Ward aldermanic campaigns since then, and though Shiller has won every one since 1987, when she ousted incumbent Jerry Orbach by 498 votes, they’ve all been pretty much the same. The ward, which encompasses a good chunk of Uptown, is more or less divided between wealthier lakefront high-rise voters who are alarmed by Shiller’s rhetoric and poorer blacks, whites, and Latinos who rally to it. Each side tries to scare its voters into turning out by demonizing the other. They yell at each other; they tear down each other’s signs; there are accusations of cheating. If there are more than two candidates in the race, it comes down to a bitterly fought runoff in which every vote is precious. (After Shiller’s initial victory, I watched her jubilant supporters wolf down Popeyes chicken and jokingly congratulate one another on the “landslide.”)

The current Mayor Daley took office in 1989 and wanted Shiller out–she was one of the only aldermen to vote against his budgets. In 1991 he endorsed Mike Quigley (now a Cook County Board member), who moved to Uptown specifically to beat her. But Quigley made the fatal mistake of allowing his campaign to be hijacked by thick-necked southwest-side galoots who stood on street corners grunting and passing out palm cards. In the end they made him look like the carpetbagging puppet Shiller said he was. She won 53 percent of the vote in the runoff and he moved back to Lakeview.

In 1995 Shiller had a relatively easy time, taking 57 percent of the vote against the underfunded campaign of policeman Bob Kuza. But in ’99 Daley’s local allies tried a new tack. Figuring Shiller had the strongest support among black voters, who make up over 20 percent of the ward, they ran a black high school English teacher named Sandra Reed. This too went to a runoff and once again Daley brought in his goons. Uptown residents (black voters included) rallied around Shiller, who won 55 percent of the vote.

It became obvious that Shiller was unbeatable at the polls, so a new strategy was proposed–to use the 2001 redistricting to carve out those precincts in which she was strongest. But none of the adjacent aldermen–Bernie Hanson in the 44th, Eugene Schulter in the 47th, Mary Ann Smith in the 48th–wanted “Helen’s voters” and the ward stayed roughly the same.

Reed ran again in 2003, but by then Shiller and Daley had reached an understanding–if she backed him he would not only back her, he would endorse her years-old plan to develop Wilson Yard, a vacant lot just west of the Red Line, into a Target and affordable residential high-rises. They announced their mutual support, the galoots stayed home, and Shiller won with about 58 percent. She’s been a fairly reliable Daley ally ever since, and in 2004 the mayor gave her virtual control over the Wilson Yard Tax Increment Financing District project, allowing her to do what she wants with the $26.5 million generated by that TIF to partially fund the $113 million development.

Shiller’s opponents–updating an old theme–accused her of using the Wilson Yard project to cram the area with poor people to maintain her political base. They settled on a social worker named James Cappleman to run against her in February, but she defeated him with 54 percent of the vote. (Daley, who won with almost 72 percent of the vote citywide, got 79 percent in the 46th.) In his concession speech, Cappleman was already talking about running again in 2011. Good luck.

After more than three decades in the trenches, Shiller has become a little like those old Democratic regulars she and her radical pals worked so hard to replace. She’s a street-smart politician who knows how to get out her vote and knows enough to support a mayor named Daley.

Art accompanying story in printed newspaper (not available in this archive): Hellen Shiller photo/Jim Newberry.