Daring to Struggle, Daring to Win: Five Decades of Resistance in Chicago’s Uptown Community

by Helen Shiller

Daring to Struggle, Daring to Win tells the fascinating true story of an individual radical organizer turned independent Chicago city council member, and her forty year struggle for justice in Chicago.

Helen Shiller went from radical anti-war activist in Wisconsin, to a member of a collective of white allies of the Black Panther Party in Chicago, to an elected city council person who helped break the back of the racialized opposition to Harold Washington, Chicago’s first Black mayor.

Shiller participated, when few others did, in the historic fight against the gentrification of a unique economically and racially mixed Chicago community on the Northside. With insight into historic community organizing and political battles in Chicago from the 1970s through 2010, this book details numerous policy fights and conflicts in Chicago during this time, illuminating recurrent political themes and battles that remain relevant to this day.


Daring to Struggle, Daring to Win is a compelling, insightful, must-read for all those struggling for a better world today.

Genres: Social Justice, Politics

500 pages, Paperback

Published November 15, 2022

Reviews

[Drew Dietz · Rating 5 out of 5]

Shiller uses her life lived experience as a bureaucracy buster in Uptown, Chicago, and how these local neighborhood struggles divulge a greater collective national truth.

Much more than an autobiography but a story telling of a community’s obstacles from the lense of a dedicated activist and social political organizer, Helen Shiller, over the course of the 1970s to present. Somewhat of a textbook but also a manifesto speaking out about against war, racism, fascism, gentrification all while advocating for accessible healthcare + housing for everyone, education opportunities, etc. when it was considered much more radical to do so.

I found her to be so personable and brilliant. A woman of many talents Helen ran a print makers studio called Justice graphics and was also a photographer, editor, publisher, badass. She literally is super woman. Being a grandma and political leader, Helen even hosted a public forum with her granddaughter, Justice, strapped to her chest. This woman literally represents the community with Justice strapped to her chest, I’m crying.

It’s a book that’s hard to put down but requires a lot of think time to think, absorb, and process. So I read it nearly twice and still feel like I want to revisit again.

[Sharon · Rating 4 out of 5]

Much of Shiller’s legacy is why I moved to Uptown, needing inspiration as winds changed in 2016-2017. I’m glad her account is documented here, though there were many moments when I thought she could have benefitted from a ghost writer to enrichen the contexts in which she worked and therefore make her stories resonate beyond people who love Chicago and people interested in the history of activism. Some stories seemed more stilted than they deserved. Still, I learned a ton that I will take with me, including about the evolution of social services in Uptown and linkages between activism in Chicago and places like Racine and Oakland.

[Deborah Wolen · Rating 5 out of 5]

I loved the parts about Harold Washington. Thanks for sharing details of your relationship with him. I appreciated Intimate details about parenting and struggling to educate in the midst of a dysfunctional school system. Thanks for the history about the AIDS finding struggle. There is a lot to learn and in this book. Thanks for such a wonderful book.,

[atom_box Evan G · Rating 4 out of 5]

Helen Shiller went up against Richard J. Daley in 1970s Chicago—that's way more badass than taking on the MAGA right today! She stuck it out, endured setbacks, and pulled off some amazing wins. Right now, we need to read and share the stories of these heroic leftist boomers—and build on their attitude and tactics.

This is a super inspiring story, told in a quiet, low-key way. Shiller humbly walks us through it like anyone could have done what she did.

As literature, the first 100 pages are true memoir: it's a story. You come to really care about young Shiller, and the narrative hangs together beautifully.

The rest of the book is still well worth reading because her life is incredible—Black Panthers, Racine, Harold Washington's campaign, the Hank Williams Homes—but as a story, it loses that tight narrative thread. No knock on her: turning a series of events into a cohesive tale is hard work. A strong editor or ghostwriter could have helped shape it further. I'm just giving a heads-up that the middle and later sections feel more like a clear, fact-based, semi-passionate account—flat in tone, but informative.

Still, I learned *so* much practical stuff about organizing and resistance. In many ways, this reads like a classic David vs. Goliath how-to guide.

If someone ever wanted to do the work of shaping this into a more fully developed story, it could be a phenomenal read. As it stands, it’s still a solid four-star book because of the rare and remarkable life it documents.

Helen Shiller's life has all the energy and drama of fellow Madisonian Paul Soglin’s. Maybe someone should pair them up and make a proper, big-budget Hollywood film. How about it, Netflix?

[Wisconsin Alumni]

Helen Shiller ’69
Author

From the author:
Daring to Struggle, Daring to Win tells the fascinating true story of an individual radical organizer turned independent Chicago city council member, and her 40-year struggle for justice in Chicago.

Helen Shiller went from radical anti-war activist in Wisconsin, to a member of a collective of white allies of the Black Panther Party in Chicago, to an elected city council person who helped break the back of the racialized opposition to Harold Washington, Chicago’s first Black mayor.

Shiller participated, when few others did, in the historic fight against the gentrification of a unique economically and racially mixed Chicago community on the Northside. With insight into historic community organizing and political battles in Chicago from the 1970s through 2010, this book details numerous policy fights and conflicts in Chicago during this time, illuminating recurrent political themes and battles that remain relevant to this day.

Daring to Struggle, Daring to Win is a compelling, insightful, must-read for all those struggling for a better world today.

[Alan Mills · Rating 5 out of 5]

Helen Shiller was already a radical when she moved to Uptown in the early 70’s. After over a decade of grassroots organizing, she became Alderman for the 46th Ward, where she held office for 24 years.

Daring to Struggle, Daring to Win takes us from her childhood in New York to radicalization in Madison, through her last term of office.

Within her personal story is a fantastic history of the last 50 years of struggle for justice and equity in Uptown, as well as glimpses of similar struggles across the US, and ranging as far as South Africa and Mozambique.

Anyone interested in the history of Uptown, the history of radical movements in the US, and anyone who is planning struggles for the future would do well to read this book.

[Eric Butler Darensbourg · Rating 5 out of 5]

Powerful book by Helen Shiller as a young black boy to man having grown up in Chicago many of the people named him the book I know personally and or have been in spaces or heard of. As a kids my parents raised my in the civil rights movement and the book captures some of the same struggles that Helen talks about. I like how she presents topics on a few pages and changes the topics so you don’t get bored. This book is about me lol and you and the experiences that must of us have been through the Good the Bad and the Ugly lol. Great job Helen and thanks 🙏 for including me in a small but important way !! Harold and especially the BPP and we as a people and folks are very appreciative of your work and courage to live the book and share. Blessings

[Viral · Rating 5 out of 5]

A wonderfully detailed autobiography from such an important figure in the modern history of the Chicago Left, Alderwoman Helen Shiller. Tells the story of how she got politicized, how she came to organizing, and the work she was a part of for decades in Uptown that ultimately led to her becoming alderwoman from 1987 to 2011. The reign of Richard M Daley was a real low point for the organized left in Chicago, and Shiller's struggles fighting for a more transformative and progressive vision for our city are worth engaging with and learning about. Everything she talks about in this book is still a problem today 12 years later, and I'm glad I got to read this and learn from her legacy as we continue to work to make the vision of her era a reality.

[Jane Ramsey · Rating 5 out of 5]

Shiller takes us on a journey through five decades of struggle for justice in Chicago and beyond. She shares her stories of how and why she became an organizer. She takes us into the struggles she worked on, how and why they developed, the building of coalitions, the Mayor Harold Washington years, her transition as an elected official and her perspective today. Shiller provides us with a unique, insightful, down to earth, fascinating journey that covers the breadth of 5 decades and manages to look forward. A wonderful book, filled with humanity, stories of courage and community, infuriating injustices fought and at times won. Highly recommend Shiller's Daring to Struggle, Daring to Win!