William Calloway hoping to take his fight from the streets to an Aldermatic seat

Without serving a day in office and at only 29-years-old, 5th Ward Aldermanic candidate William “Will” Calloway has spurred more change to Chicago than most aldermen who have served for decades. Part of that may be because most aldermen have served as rubber stamps to Mayor Rahm Emanuel and before that, Mayor Richard M. Daley. But since Calloway came to the attention of the public, his actions have led to reform in the Chicago Police Department, the ouster of the Cook County State’s Attorney and Chicago Police Superintendent, as well the decision by Mayor Emanuel not to run for another term. 

Calloway, known as a community organizer, became known to the public as the man who, along with independent journalists Brandon Smith and Jamie Kalven, helped get the Laquan McDonald video released. McDonald was the 17-year-old who was shot 16 times by Chicago Police officer Jason Van Dyke in 2014, which led the the first murder conviction of an on-duty Chicago Police Officer in 50 years and along the way rid Chicago of its top legal and political heads.

Now Calloway, having already made significant changes from the outside, is vying to continue his mission on the inside by running for Alderman in Chicago’s 5th Ward, which encompasses the South Shore neighborhood.

It was there, at Calloway’s campaign headquarters at 2030 E. 71st Street, that the Chicago Ambassador’s Bob Chiarito sat down with him to talk about his journey and his plans going forward.



CA) First of all, let me back track a bit. People know you as the activist who got the Laquan McDonald video released, but how did you begin with your activism. It was before that, right?

CALLOWAY) Yeah. In 2012, I was in film school at Columbia College making a documentary about Chicago violence. I was invited to a seminar by the Chicago Alliance Against Racial and Political Oppression. They were hosting a seminar at the University of Chicago about police violence. I thought it would be interesting to go there and get some footage for my film. I went and heard people speak who had been brutalized by the police. Victims of excessive force, police misconduct, false arrest. Then, at the end of it all, there was a gentleman who got up and started to talk about his sister, who had been shot in the head by an off-duty police officer. His sister was Rekia Boyd. He spoke with a lot of conviction and at that moment, that’s when I felt compelled to get involved. At that moment, I didn’t know all of this stuff that has transpired since then would happen. I just heard what happened to him and thought, ‘Man, that’s messed up.’ I offered my condolences to him as a human being and told him whatever I could do. Me and him kept in touch and I kept in touch with that organization. Ultimately the officer got charged with involuntary manslaughter, but the case got dismissed. During that time, I started meeting more people through that organization and just throughout the city of Chicago whose kids shared similar stories like what happened to Ms. Boyd. I started organizing these families, it started to become a community. First it was one, then it became two. Then, two became four, four turned to eight, and eight turned to more than a dozen. That’s how I got involved, that’s how my activism started. 

CA) Obviously your activism inspired you to run for Alderman in the 5th Ward. 

CALLOWAY) I’ve always been civically engaged. I’ve been like that since I was a teenager. 

CA) What neighborhood did you grow up in?

CALLOWAY) I grew up in the south suburbs and Englewood. I was born in Englewood. I was adopted, so I moved around a lot. I lived on the South Side of Chicago, Calumet City, a small town called Lynwood…

CA) Just to go back to what you said after your remarks after Jason Van Dyke was convicted, were you frustrated or disappointed — what was your feeling about the fact that none of the black politicians were there every day, or there at all in most cases?

 CALLOWAY) I just felt real disappointed. I’m not going to say disappointed, because I’ve been disappointed by the black caucus and the City Council for years. I was beyond disappointed. It spoke volumes that no elected officials, especially no one of African American descent came out to lend their voice or influence of their office.

CA) There wasn’t any white or Hispanic politicians there either.

CALLOWAY) None of them came out. I think that people need to realize that when they cast their ballots, because these Aldermen are responsible..these career-long politicians have voted for hundreds of millions of dollars in police settlements. Laquan’s settlement was $5.5 million, that’s just one. If you do that a hundred times, that’s half a billion dollars. Since some of them have been in office, they’ve done that a hundred times. 

CA) With the Laquan McDonald, there wasn’t even a lawsuit.

CALLOWAY) Nope, there wasn’t even a lawsuit.

CA) And they held the video for a year.

CALLOWAY) 400 days. And [Garry] McCarthy tried to say all this stuff that it wasn’t his fault, that there was only so much he could do. Listen, you were the most powerful law enforcement official in the city with the third largest police department in the country. You could have used your voice and spoken truth to power, regardless.

CA) It seemed like every citizen had an opinion regarding the Van Dyke trial, yet no politician showed up. Are they just not listening to the people?

CALLOWAY) They’re comfortable. They’re complacent. They went from Black Panthers to Pink Panthers. And the Chicago voter turnout is very low so…

CA) Do you think that your generation and the younger generation — especially among African Americans, turnout has always been low. But do you think there’s a disconnect between them and the people who are in power right now?

CALLOWAY) I think so. I think my generation is skewed by the whole democratic process in general. They don’t have any hope in politics, especially in the black community.

CA) A lot of times people try to change it from the outside. But you’re trying to change it from the inside now by running. 

CALLOWAY) I would like to think and believe that I’ve done a lot from the outside. I just think at this point in my life, I’d like to change things from the inside.

CA) Do you think if you win that you’ll be able to do more?

CALLOWAY) Yeah, a whole lot more. I’ll have elected official powers and that will help, especially in a ward like this.

CA) There are some sparks of life, or energy, with the younger community. For instance, Amara Enyia was endorsed by Chance and Kanye West. Maybe things like that will help get some out to vote?

CALLOWAY) I think it’s going to take more than that.

CA) A lot of times, the press seems to lump groups together under one umbrella. I think the press has been guilty of that for years. For instance, for a long time the press let Jesse Jackson speak for all African Americans, but one voice cannot represent an entire group.

CALLOWAY) That’s true. All of us are individuals and some of us are more independent thinkers than others. Therefore, you have that group who doesn’t want one person speaking for the whole collective, and then you have others that may want one voice to speak for a group that feels marginalized.


Calloway after Jason Van Dyke was found guilty


CA) Do you think that things may change since Rahm Emanuel is leaving, since some of those politicians who were afraid to speak up will be free to?

CALLOWAY) Yes, but I also think we should have a weak mayor, strong city council system. For the past few decades, it’s been the opposite. We want to strengthen the City Council, create more reforms and more oversight. I think we a City Council Inspector General. 

CA) You’ve said there are a lot more cases like the Van Dyke case that the public isn’t aware of. 

CALLOWAY) Yeah. There’s a bunch of them. 

CA) Do you think a lot of these Aldermen, as you said, just got ‘comfortable’ over the years and didn’t want to push the envelope anymore?

CALLOWAY) I think so. Of course, I’ve going to be biased but I don’t want to come off as biased. We went out and were knocking on doors this morning and I asked one of the homeowners what her concern was. She just said that Leslie [Leslie Hairston, 5th Ward incumbent] has been in office too long and has gotten complacent. She’s been in office for twenty years and no one should be in office that long. Not only that, but you have nothing to show for your work for the last 20 years. If you look at 71st Street, it’s been on a constant decline year after year. This is our sixth consecutive year of having a food desert after Dominic’s left in 2013. There was no substitution for that, no Mariano’s, no Whole Foods. So, on top of that there’s the violence. I’ve watched a lot of people who have walked past this office that are no longer here. Even my friend, One Step. His name is Darnell Bass but his nickname is One Step. He died in October and I dedicated my campaign to him. Hence, the phrase ‘Stepping Up.’  [Calloway’s campaign slogan is ’Stepping up for the 5th Ward”]

It’s just the violence and her [Hairston’s] lack of response to it. She doesn’t come out for anything. 

CA) Let’s jump ahead and assume you get voted in. How do you guard against becoming like that?

CALLOWAY) I was just thinking about that. I said something to myself earlier. I didn’t like something I said and I had a thought that ‘I don’t want to think like that.’ So, I definitely have a spiritual base, a moral compass that I always adhere to. I surround myself with an inner core that I’m accountable to. People that I can be completely transparent with with can tell me, ‘No Will, that’s not a good idea’ or ‘This is how I authentically feel about this situation.’ People that can keep me grounded and level. I think it’s important to have people that keep you accountable and also lift you up. And quite frankly, not stay in that office that long. That’s the ultimate thing.

CA) You don’t want to be a career politician?

CALLOWAY) I do not want to be a career politician. No one in our community, and that’s what is so frowned upon — they do not groom anyone to be their successor. That’s something that’s frowned upon the most, especially in the black community. We have these leaders who have been in there for decades but they won’t pass the mantle to anyone younger or anyone else. I don’t want to be that. We were just joking about it before you came but it’s the truth. There’s no way Ed Burke was there 50 years and didn’t do anything corrupt. In Chicago? And you’re the head of the Finance Committee? [Laughs] You have to know when to hold ‘em and when to fold ‘em. I do not want to be a career politician.

CA) Any idea of how long you want to be in office for?

CALLOWAY) No more than two or three terms. I’ll say this — no longer than fixing what needs to be rectified, so even if it’s in my first term – if we get a grocery store, if I feel like we’ve reduced the level of violence, that we improved the housing issue and other issues, I’ll be like ‘It’s probably best for me to move on to something else.’

CA) But what happens if things don’t get fixed. Would you stay in office for thirty years if stuff is still going on?

CALLOWAY) No. It’s like basketball or any pro sport. I could sign you for a deal and bring you on, but if you’re not performing I’m either going to trade you or cut you. I think people have to be realistic with themselves and say ‘Maybe this is not a good fit for me’ if you aren’t delivering on what the people are paying me and entrusting me to do, you need to step down. 

CA) Is there any politician in office that you talk to for any type of advice or is your attitude towards them negative?

CALLOWAY) All of them to me are bad. You have some that try, but I don’t need you to try, I need you to deliver. This is a state of emergency. You have people who need to be more deliberate with their position in office. 

CA) Perhaps they are hedging their bets instead of taking a stand?

CALLOWAY)  While they are doing all that, we are starving and dying. I’m tired of people playing with our lives. 

CA) Is there anyone else that is running that you’ve been working together with?

CALLOWAY) Yes. Jedidiah Brown is running for Alderman in the 7th Ward, which is adjacent to this ward. Joseph Williams is running in the 15th Ward. There’s a young lady named Cleopatra Watson who is running in the 9th Ward, I really like her a lot. 

CA) These people are all newbies?

CALLOWAY) Jedidiah has a track record, I’ve known him since I was a shorty. He has an excellent track record for community organizing. He ran in this ward during the last election but now he’s living in 7. I met Joseph Williams about a year or two ago. He’s a community organizer who does a lot for black family empowerment. I just met Cleopatra recently and really like her heart and her ideas for her ward. She really wants to unseat the incumbent, Anthony Beale who votes 100 percent with the mayor.

CA) This kind of goes back to the question about one person speaking for a whole group, but do you think there are too many different groups out there, where there is not a consistent or focused message?

CALLOWAY) I just don’t think there’s anyone effective. You can have different messages all you want, but there isn’t anyone who is bringing any substantive change. I feel like I was part of a group that brought substantive change as far as police reform. We’ve done in the past several years what people have been trying to do for the past several decades with the Chicago Police Department.

CA) Without your successful lawsuit for the McDonald video, we probably wouldn’t be sitting here right now.

CALLOWAY) I think that’s important but I think what people have to understand is that even with that tape coming out, the ground was already softened. The Laquan tape just took things to a whole different level. We were already in the streets by the thousands for so many other police related issues. That tape, all it did was validate everything that we were saying. Then you couldn’t contest what we were saying anymore because we had actual proof that the Chicago Police was using deadly unnecessary force against African Americans. 

CA) In the 1990s, reporters like myself used to hears stories like that all the time, but back then no one had cell phones and videos. So, it was like, who are you going to believe — this guy whose been in and out of the system a million times or these cops?

CALLOWAY) Always believe the community.

CA) But as a reporter, you can’t just take someone’s word without anything to back it up. We could write a he-said, she-said story, but that would be it. 

CALLOWAY) The ironic thing, what people fail to realize is that after the Laquan tape came out, he was the catalyst. He was like the Emmett Till of our generation. There were tapes after the Laquan tape that I wanted to go after that Rahm and the law department did not want released. Cedric Chapman, Ronald Johnson, Alfontish Cockerham.  We got them out.

CA) What’s the key for you to win? Is it to get the young voters or to get the people that already registered?

CALLOWAY) I think the latter. We are taking an inter-generational approach. I’ll do well among my peers, naturally. But seniors come out to vote more. 

CA) They always do. Seniors seem to vote no matter what.

CALLOWAY) But on November 6th, the millennials voted in record numbers. If that trend continues in February, not only will I win but it will be a landslide.


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