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On the Campaign Trail with Black Lives Matter Activist DeRay Mckesson

We spoke with the social media-savvy activist about his decision to enter Baltimore's crowded mayoral race.

by Annalies Winny
14 April 2016, 12:00am

Photos by Shane J. Smith​

Portrait by Shane J. Smith

A version of this article appears in the April issue of VICE magazine. Click HERE to subscribe.

Since making his name as an outspoken leader during the protests in Ferguson, Missouri, DeRay Mckesson has been somewhat of a wandering activist. After police officer Darren Wilson shot teenager Michael Brown, the public school administrator made a spur of the moment decision to join the marches, leading him on a path to Twitter fame. He has since become a prominent voice of the Black Lives Matter movement and the police reform plan Campaign Zero. Mckesson has been a force at protests in his native Baltimore and, more controversially, Charleston, South Carolina, where he inspired the ireful hashtag #gohomederay. Now he has gone home. The Bowdoin graduate and Teach for America (TFA) alum is a candidate in Baltimore's crowded mayoral race. Expanding his repertoire by going local, Mckesson is now fielding questions far beyond his stance on police brutality, and he is setting out to prove to naysayers that Twitter's best-known activist is ready for local politics.

VICE: You've gone up against the Establishment and tweeted your experience. Why do you now want to be a part of it?
DeRay Mckesson: A key part of the movement has been about telling the truth in public and that remains the same. In the movement, it was about making it work in the sense that the police didn't kill people. Running for mayor is based on a sense of, "How long do we wait for change to come?"

How did you get to this place?
On August 16, I was sitting on my couch. It was one in the morning. I saw what was happening on Twitter, and I was like, You know, I'm going to go. When I went, I had eight hundred followers on Twitter. I went to bear witness; I was going to go stand in solidarity. The second day in, I became a protester. I got tear-gassed the first day of the curfew. I'll never forget it. It was this feeling of, "This is not the America I know."

What was the America you thought you knew before that day?
I grew up in a world of Officer Friendly. It was just the image I had. I had been pulled over in 2009-ish, and the officer came to my car with his gun drawn, but that to me was an isolated incident. It wasn't until Mike [Brown] was killed that I realized that this is everywhere. There's a Mike Brown in every town. This is much closer to people than they thought it was. Until then, I never thought that I'd be tear-gassed on an American street for saying that the police shouldn't kill people.

How did you decide to take this on?
This has been quick and thoughtful. Leading up to it, I got a lot of feedback from people in the city about it, and I was like, We can't wait any longer. The time is now, right? What have the traditional politicians gotten us? There has been one path to politics in this city for too long.

What is that path?
Join some local club, become a city council person or state senator, serve on some board or commission, then run for mayor after you've "paid your dues." People in power make the path to power. It means that we will always get the same system, and it's one that is not necessarily in the interest of people's lives. It doesn't work for people that the homicide rate is so high; it doesn't work for people that the schools don't meet people's expectations.

On Stephen Colbert's show, he asked you to help him understand what white privilege is and how he can fix it. For me, the humor of that segment was that it was really hard to come up with an answer. All jokes aside—can you define that?
When I reflect on the Colbert interview, it moved so quickly that what we didn't do was define white privilege, and I wish we had done that. White privilege is the benefit resulting from white being seen as the standard, regardless of gender and income. Just because you didn't create it doesn't mean you didn't benefit from it, right? People say, "I didn't own slaves. My mother didn't own slaves," as a way to suggest that the privilege of whiteness is not real. What people can do is understand that the privilege exists and use that privilege to create space for people who don't have it. The way that we recruit and the way that we think about developing people's skills has to take into account the intergenerational, intentional trauma that has happened.

You've taken on issues around white privilege and black struggle. How does that gel with your mayoral run in a city dominated by black leadership?
Just because there are black people in leadership doesn't necessarily mean that the outcomes change. It does mean that people come to the role with a different perspective, and there's this hope that the perspective informs how they make decisions. I think there's a lot of work to be done around undoing the impact of racism across housing, schools, and healthcare. But I have trouble thinking about its relationship to black mayors. I think the assumption is that people's experiences will help inform the way they make decisions. I get the assumption. I also understand that it's an assumption.

Sounds like you have a fundamental problem with the power structure whether it's black or white or purple people running it.
This city is one of the birthplaces of redlining, hyper-segregation, and a whole host of other ills that are a direct result of not only racism but also its legacy that is deeply rooted in racism itself. White privilege is a soft way to say it. The legacy of racism and its impact on communities in Baltimore is still felt. My challenge is with the world that is created by people's actions. Whether they're black or white, what kind of city has this become because of your leadership? What kind of city has this not become because of your leadership?

Much of your national profile has been about digital engagement. How do you approach it?
I think about Twitter as the friend who's always awake. Half of it is for me to process the world, and half of it is for me to share things with the world. I like waffles, and I tweet about that. I talk about the news, and I talk about issues relating to equity and justice. That's a big part of the world I want to live in.

But how will your mastery of social media help Baltimore?
For so long, people have thought about working with city hall as showing up to forums and coming to hearings. We can use technology to bring conversations into the public space in new ways. What Twitter allows us to do is to connect with people differently. I want to make sure there are so few barriers to how we interact—that there's space for us to have conversations that we might not have had before.

What's one big shortfall in the government sector that could be helped by your experience?
Accessibility. Traditional public comment looks a certain way and feels a certain way that isn't necessarily responsive to people's time, people's passions, and people's energy. Technology can change that. So if you can't get off work because public comment is only from six to seven at night, then, like, we can use technology to capture that feedback. But we can also gauge what people want, gauge people's expectations, and all of that matters.

As a national figure, is being the mayor of Baltimore the best use of your time right now?
Yes. What we did in protest, and what people continue to do, is tell the truth in public. We put pressure on systems to do right by people. What I've learned over the last eighteen months is that much of this work happens at the city level.

I want to make concrete changes to peoples' lives today and tomorrow. Maybe I'd go retire on a beach and tell people, "Get free."

But this is a developing role for you, which is kind of fundamental to the fact that you're an outsider here.
I'm learning so much. It's interesting to see people who have been willing to challenge the system in protest, but unwilling to challenge the system in this way. There are people who have demonstrated their willingness to challenge systems and structures, and then when it comes to elections, some of those same people—I don't know where their fight went. What's interesting to me is to see people lose the revolution when it comes to elections.

Who inspires you?
Diane Nash, a civil rights activist, once said to me: "If we had listened to all the people who told us there was a right way to do this, we never would have done it." I think about her often. And I think about all the people who told us to go home in August 2014. Look what happened. I know that we didn't invent resistance and discover injustice last August. So many people had been doing this work way before me.

One local activist said he had a "serious question" about your commitment to the concerns of Baltimore citizenry. What's your response to that?
People feel like I should have asked them for permission to run for mayor. Just because you haven't seen me doesn't mean I have not been doing work. I think there are many ways to do this work, and that are all important. I've been an activist and organizer in Baltimore City since I was 17 years old. I would never suggest that, just because I did not personally know somebody, they weren't committed to any issues around social justice. I think that's a dangerous way to think about the world.

What about Teach for America? People have a lot of criticism about your relationship to that organization.
It's this frustrating thing that I'm a proxy for people's frustrations. I was a core member from 2007–2009, and it's one of many experiences that have informed my understanding of the possibilities and promise that exist in cities like Baltimore.

To suggest that the one or two years that people taught didn't matter, I think isn't fair to the profession itself. I understand people suggesting that you should stay in the profession for a long time—that makes sense to me too—but to suggest that people shouldn't do it the way that you did it, that it doesn't matter, just isn't fair to the profession.

There are people who are very frustrated with TFA. I think people hope that I come out and say TFA is bad for kids. It's an imperfect organization like so many others. And people should rightly challenge it to be its best. I taught with so many other people who not only entered the profession with the right mind, but to achieve results and do good things for kids. Nobody wants to hear this, but the data does not suggest that TFA teachers do worse than anybody else—they do just as good as anybody else.

There isn't much mention of charter schools in your platform. What's your stance on that?
There is no one-size-fits-all to it. I'm reminded that teachers started charter schools. At their best, they're rooted in one question: Is there an opportunity to innovate when there are fewer constraints? That is the root of the philosophy of charter schools. I think where people's frustrations come in, and rightly so, is around what happens when there are no constraints and no results. And we should hold them accountable. We shouldn't experiment on kids—we should be thoughtful.

It's true that teachers can start charter schools, but they do create more of an opening than the city-run schools for more private investment and running schools as a business. Critics really push against that.
There's this weird thing where it's like, DeRay supports privatization of schools. I don't know where that comes from. People struggle with this mythic idea of charter schools—about innovation that will flow from fewer constraints, and that makes sense to me.

Schools are schools; they occupy such a unique space in the public domain. I don't know who people think are financing public schools! Do people know how much private money goes into public schools? It's very odd to me. Schools should be run like schools, but some of the stuff does need to be run like a business. Educators for instance—I think about myself, as somebody who had to recruit bus drivers, and let me tell you, I'm smart, but I'm sure there are people who, like, should actually be recruiting bus drivers.

I read your plan about public safety. Almost all of the Democratic candidates you included are talking about efficient rehabilitation, helping offenders back into society for everyone's benefit.
You should be able to be a child with the fullness of what that means and make it to adulthood and be able to thrive. You should be able to make mistakes and survive them. You should be able to laugh and fall in love and experience joy and live to eighteen. That's what I say to kids. I want there to be support systems around you, and I want there to be systems and structures to be a part of that safety net so that you don't fall through the cracks.

You also said you want to hire people most affected by police violence to conduct mandatory anti-racism training for the police, with implications for officer performance evaluations and decisions about deployment. That sounds like a minefield to implement.
Did I put that in there? I'm kidding. If people subscribe to the notion of community policing, then the community should be able to be part of both ends of that equation. They should not only be the people at the end of it, the people who are policed. They should be on the front end. It's another way to reinvest in community, where we can take dollars that are ostensibly given to some experts who don't actually understand communities and put them with the people who we definitely know understand communities—the people who live there.

So when you say people who are most affected by police violence—I take that as a bracketed group of people I think that could include any number of people, useful and less useful to that process. How would you vet that group?
I think that there a million ways we could do it. We could look at the demographic that is most heavily policed and ask those people if they'd be interested in this type of experience. The training needs to be high quality. It's about being intentional about who delivers the training. I think there's an assumption that people who have been impacted by police violence don't have things to teach and don't have things to share. I don't live in a world where that assumption is true.

The field is crowded in the race to be mayor. If you don't win, what are you going to do?
I think we'll win.

OK, if you do win, here's the classic question: Where do you see yourself in ten years?
I'm excited about being the mayor of Baltimore. I want to make concrete changes to peoples' lives today and tomorrow. Maybe I'd go retire on a beach and tell people, "Get free."

A version of this article appears in the April issue of VICE magazine. Click HERE to subscribe.