A Pioneering Chicago Politico Talks Winning, Losing, And Becoming An Insider

Bobbie Steele grew up in Cleveland, Mississippi, in the 1940s and 1950s. It was hardly inevitable that she would end up with a decades-long career in Chicago city politics. But a few years after her retirement, Steele has an impressive career to look back on, with stints as a teacher, a member of the county Board of Commissioners, and the first woman to hold the title of Cook County President.

Steele moved to Chicago one summer while she was in college to raise money for her next year of school. There she met a man named Robert Steele, who she says “came on to me like he was meant to be in my life.” They married six months after they met, and Bobbie Steele continued her studies in Chicago, eventually earning a Master’s degree. From there, she built her career in teaching and then in city politics. She retired a few years ago, she recently published Woman of Steele, a book about her life. She spoke with me last week about her advice for young women interested in public service, what it was like to be one of only a few black women in the room, and the one election she’s glad she lost.

How did you get started in politics?

After marriage and starting to raise a family, I got involved in community work. The neighborhood we lived in was very poor. … I got deeper and deeper into community work, and as I was going to night school to finish college, I began to be called upon to be a leader in the community. By the time I finished college, I was really well steeped in community work. I got involved with the Chicago Teachers Union, and I was the union rep in my school. Years later, when Harold Washington came along and announced his candidacy for mayor, I thought that was a new opportunity for people who wanted to be insiders who had always been kept outside.

Washington became the city’s first black mayor in 1983. It was his candidacy that pushed you into politics?

I immediately signed on to that campaign. I got so involved that I suddenly was then running for alderman of my ward. I was teaching school, and I had no money, and I said yes, like an idiot. In those days the Democratic machine was vey strong. So those who were part of the democratic process were treated differently from outsiders who wanted to come in. I was an outsider, but I agreed to run. Of course I was not successful! But I connected with a lot of people across the city, and certainly with Harold Washington in a big way. He always kept me nearby.

In 1986, you ran for and won a seat on the Cook Country Board of Commissioners. What was your proudest accomplishment in your years in that position?

The one thing I’m the proudest of is being in a position to provide services for uninsured citizens of Cook Country through health care. I did that through being chair of the Provident Hospital committee, which gave me the responsibility of overseeing the reopening of a shuttered hospital, seeing it rebuilt, and putting it back on the rolls of active hospitals in the city of Chicago.

In many settings in your career, you were one of only a few African-American women. Was that challenging?

Being alone is not a comfortable position to be in. But having the training that I’ve had, I’m reminded of what my mother told me: better to be alone than in bad company.

How did you deal with situations where you were in “bad company”?

I learned to be an observer, and learn where and how to deal with the male gender. That helped me to be re-elected the six times I was re-elected to the board. You have to learn when to roll it, when to fold it, and when to walk away! There are men of certain age groups who will listen to you, and certain age groups, the older ones, who won’t. … If you become a good observer and learn the behavior of your male counterparts, i learned you can make progress.

You ran for Congress in 1995, but you write in your book that in some ways you’re glad you didn’t win. Why?

I worked hard [on the campaign] and my family helped, as they always do. But their heart wasn’t really in it. To not see my grandkids grow up, the hassle of going back and forth between Chicago and Washington … People said, ‘You can win,’ but when it came to raising money, they weren’t there. It costs a lot of money. We did our best, but it’s an accomplishment I didn’t get. I have 14 grandkids and I can see them all graduate high school — four more coming out of high school, and five in college. That bonding would not have been there if I had [been in Congress].

Do you have any advice for young people who might want to follow in your footsteps?

Be sure if you’re interested in running for office that this is something that you really want. Be sure you have a support network to help you with family, if you have a family. Make sure you have a track record of doing something — volunteering for anything of interest to you. It’s important that you make a statement with your history when you don’t have money to run for office. At least you have a name to sell to the people. So do something. Do something with your life early on, something you enjoy. If you have any interest in running for public office, get started.

It’s nice to hear someone who’s not disillusioned about public service, even after a long career.

A lot of people look at Chicago politics as something that’s corrupt, but it’s not all corrupt. There are a few people who have fallen by the wayside because of greed or mishaps, but politics is not all dirty. We need creditable representatives in public service. There will be stories of politicians who have fallen by the wayside, but that doesn’t represent the majority. My recommendation is to be open, honest and fair in making a judgment about public service. It’s just like any other business.

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      I could say that I have known this woman of steele all of my life, but she is not as old as I am, so I will say that I have known her most of her life and can attest to that all of the matters contained in the above article are factually true. She is one to be admired and looked upon as a role model both socially and politically. As an aside, now that she has sold her bestseller book, she can pay me back the $12.oo I loaned her in 1975.