Shiller's oral history was collected by Pulitzer Prize-winning author and Uptown resident Studs Terkel in his 2003 book, Hope Dies Last.

[5] Shiller graduated with a degree in history from the University of Wisconsin–Madison, where she was active in the anti-Vietnam War movement and in the Students for a Democratic Society (SDS).

[3] For decades Shiller and her allies worked to preserve Uptown as the last North Side lakefront neighborhood south of Rogers Park that is home to a significant population of low income households.

[16] On March 6, 1978, Ralph Axelrod, chief administrative assistant to Cook County Sheriff Richard Elrod,[16] and ward committeeman since 1973, slated himself for alderman.

[16] He was running primarily as a defence against the FBI's CointelPro repressive program and to expose the displacement of Latino and lower income areas from the lakefront and near downtown by the Richard J. Daley machine.

[failed verification] Shiller's base of support was the same geographic center of the ward, an area of high density, low-income families between Broadway and Clark Street.

[16] Independents including Aldermen Dick Simpson (44th), Martin J. Oberman (43rd), and Ross Lathrop (5th), and former alderman and mayoral candidate William Singer (43rd), endorsed Angela Turley, founder of the Organization of the Northeast (ONE), a community group.

[18] Turley and another candidate Carl Lezak, a former priest and former director of the American Civil Liberties Union (ACLU), were challenged and stricken from the ballot by the Chicago Board of Elections Commissioners, leaving a three-way race for alderman between Axelrod, Shiller, and former television news reporter Michael Horowitz.

[25] An extra alarm fire early on Friday, February 9, 1979, weeks before the election, caused extensive damage to the building containing Shiller's campaign headquarters and left 15 homeless.

The Chicago Tribune wrote that "Ms. Shiller's program shares many elements with that of the Black Panthers and appears to be based on hopes of an eventual "revolution" [not defined].

"[30] Axelrod enlisted 40 volunteer attorneys and 200 off-duty policemen to challenge ghost voting in a project he called "Operation Safeguard."

[5] Justice Graphics published the All-Chicago City News,[32] a 40,000 circulation pro-Washington, left-wing, bilingual, biweekly newspaper[33][34] edited by Shiller and Walter "Slim" Coleman.

[49] Shiller charged that Orbach catered to developers, displacing people in the wake of rehabilitation that priced housing out of the reach of many, and said she wanted community zoning boards, with their decisions binding on the alderman.

[57] Jesus People USA, a 500-member commune/business/charity/religious group with many members living in the ward, had supported Orbach throughout his career, but switched to Shiller before the run-off.

Mayor Washington's budget recommendation included a $20,000 grant to UCC to facilitate residents applying for home improvement loans.

[68] The Uptown site west of the Wilson Chicago Transit Authority (CTA) station was opposed by those concerned for the displacement of low income residents, largely blacks, southern whites and American Indians.

[65] On October 28, 1987, Shiller urged the Tax Delinquency Subcommittee of the Cook County Board to accept a no-cash bid from the city for the 19 tax-delinquent parcels in Uptown.

Subcommittee chairman Commissioner Richard Siebel said the county's no-cash sales program was "designed to place property back on the tax rolls as quickly as possible – not for land-banking.

"[72] As a bench ruling in Avery v Pierce neared, Shiller proposed an ordinance that directed the city to settle and accept a consent decree.

[8][77][78] The consent decree would have put most vacant parcels in Uptown into a land bank for future affordable housing, administered by a community development corporation, funded by the city with $100,000 over two years.

On November 16, 1987, the Committee on Finance of the Chicago City Council, chaired at the time by Shiller ally Alderman Timothy Evans, voted 21 to 2 to recommend the consent decree.

[79]In 1988 Royko wrote of Shiller, "her main motive was that she was building a political power base, which included as many winos as she and Coleman could drag to the voting booth.

[76][77][80] The Chicago Tribune called the proposal "silly," editorializing: It would have enabled her [Shiller] to strangle commercial development in her Uptown ward and keep it poor.

It would have put Helen Shiller and her sidekick, Slim Coleman, in charge of a "community development corporation" whose avowed purpose would be to block private investment in the 46th Ward and use all available space for low-cost housing.

[105] In 1999, Sandra Reed, a black high school English teacher, and two other women opposed Shiller, the first all-female field in an aldermanic race in Chicago history.

The last independent voice had joined the chorus ... Shiller's endorsement of Daley is all the more amazing when you look at where she started, about as close to a Marxist as you'd ever find at City Hall.

[116] Shiller was the only alderman who did not cast a vote on the passage of the Big Box Ordinance, which required large retailers to pay a living wage.

... we have to have a city that is not just inclusive about our diversity but is serious and honest about making sure that everyone has a place here ...[128]On closing her ward office, Shiller wrote: I am most proud of my achievements in tripling the City's funding budget for HIV/AIDS victims and for developing the toughest stance on Apartheid that was ever written in the 90's, for my work on domestic violence issues and establishing 24-hour daycare for children, the Ruth Shriman House for senior living, the Wilson Yards Development and for welcoming Target as a neighbor and partner, and of course setting the bar for affordable housing in Chicago.

In 2014, her son Brendan, a defense attorney, found a few empty buildings on Chicago's west side and laid out a vision to his mother that included setting up shop for his law firm, Shiller and Preyar.

][136] Helen Shiller and her long-time staff member Maggie Marystone were interviewed in separate chapters in Hope Dies Last, a collection of oral histories by Pulitzer Prize-winning author and Uptown resident Studs Terkel.