DeRay Mckesson and the lessons of ‘Freedom’
Ahead of Houston book visit, teacher turned activist-politician reveals what he’s learned
Four years ago DeRay Mckesson’s life shifted as seismically as California during an earthquake.
In 2014, he was the senior director for human capital in the human-resources department for Minneapolis Public Schools, reportedly making just over $100,000 per year and leading a relatively comfortable Twin Cities life. Then on Aug. 9, African American Michael Brown was shot and killed by white policeman Darren Wilson on the streets of Ferguson, Mo., an act that launched a national conversation about race and sent the streets of the St. Louis suburb into convulsions of protest against abusive police and systemic injustice.
Mckesson, a former teacher who had long worked in community activism, knew that he had to be there, even though it was more than 500 miles away. That journey kickstarted the next
phase of his life. What was supposed to be just a weekend seeing what was going on in Ferguson first-hand turned into a calling.
He quit his job, moved to St. Louis, threw himself into the protest movement, got arrested and devoted his time to the issues around the country’s heated racial climate. He, along with his trademark blue vest, became one of the best-known faces associated with the Black Lives Matter movement and, in 2016, he ran to be mayor of his hometown of Baltimore, though Mckesson came in a distant sixth in the Democratic primary.
Now, he’s documented his journey with a compendium of memoir, diary and how-to guide, “On the Other Side of Freedom: The Case for Hope,” a book that not only deals with his political awakening and societal prescriptions but also deeply personal issues such as having his mother walk out on the family when Mckesson was 3 and his coming out as gay. The nine months he spent writing it were often quite wrenching.
“Writing about this is sort of like dying a little bit,” Mckesson, 33, said in a phone interview and then laughed. “It’s like dying, but there’s an end product.”
But he knew had to get it all out.
“A few people have asked me to write for a while,” said Mckesson, who will be appearing Friday at The Ballroom at Bayou Place in downtown Houston as part of a 16-city book tour. “I listened to a sermon; the sermon was titled ‘Don’t Tell Your Story Too Soon.’… What he said was that sometimes you can tell your story so soon that all you can see is the pain, not the purpose.
“If I had written the book two years ago, it would have been a play-by-play of the cities I was in … I was so close to everything that I wasn’t able to step back and say, ‘Here are the themes. Here’s what I learned.’ Now, I’m at a place where I can actually think about my mother, think about how I remember her, how remembering her changes the way I think about a lot of things.
“There’s a bigger lesson in that that applies to this work. I’ve never written about being gay, though I’ve been out. It was important for me to write that down, to get it beyond myself and to share it. We’ve done so much work around the police that we never really put anywhere. It’s online and we’ve tweeted about it, but I wanted to write that. There were all these stories that I’d been carrying that I hadn’t put in one place, and the book was my way to do that.”
The process was painful as he felt he couldn’t write a book just about politics.
“The personal is political, and there are so many things that I never publicly talked about,” he said. “I never talked about the impact of (my mother) leaving and how I thought about that. So I wanted to write it as a way for me to process it and think about how it impacted me politically and what that means to me.”
So what does it mean to Mckesson?
“Part of what I think it means to show up is to be vulnerable and to share our deepest truths, especially as we try to do the work of building a world that our lives deserve. And I did not know how to do that without talking about my personal life. … Some people think I’m static with no feeling, but really it’s just me holding these things really close because I’ve always thought that holding them close is what keeps me strong in the work. I had to learn that strength comes from sharing and being vulnerable.”
None of this might have happened if Mckesson hadn’t made the seemingly rash decision to head to St. Louis that fateful day.
“A kid got killed in St. Louis, and St. Louis isn’t too far. If I say, ‘I stand with kids,’ the least I can do on a weekend when I’m not doing anything is stand because this kid got killed. That’s the bare minimum, right?,” he recalled thinking.
Still, the lightbulb moment for him was not going but staying in St. Louis. “What was harder was Sunday night comes, and I have to be at work on Monday and I don’t go to work on Monday,” he said. “I got the work done and I took days off (but) I eventually left the district. I depleted my savings account. I defaulted on my student loans. I depleted my retirement. I said, ‘This just feels right, right? I’ll get another job.’ I made six figures (but) that wasn’t the metric of what success looked like for me. … This actually feels like I’m making an impact.”
What kept him in St. Louis was more than just a cause. “It was a sense of community that we all found in protest,” he said. “It was the most incredible experience I’ve had in my entire life. If you ask anybody who was there in the early days, the sense of joy and community that we all shared was something I’ve never experienced before or since.
“One of the beautiful things about St. Louis is that we all had a perfect sense of tunnel vision when we were in the streets,” he continued. “It wasn’t until the first wave of protests ended and we started to go other places that I first realized that the world had been watching us. The tunnel vision was beneficial to us all in hindsight. When things like money and visibility started to get introduced, it changed the texture of how the community came to be.”
What may surprise some readers about “On the Other Side of Freedom” is the sense of cultural optimism that snakes through it like a river. Despite the fractious times and often poisonous political atmosphere, Mckesson is not downbeat about the future.
“I don’t think it’s about optimism as much as I think it’s about hope,” he said. “That hope is this understanding for me that tomorrow can be better … I definitely had my moments when I was like, ‘This is not looking good. This is rough.’ But I have always maintained this notion that when people come together, we can do powerful things. Being in the street in Ferguson cemented that.”
He’s been trying to put that hope into practice since returning to Baltimore, a move that ruffled some feathers. In addition to throwing his hat into the mayoral race, something that prompted some barbed criticism from locals who felt he was not sufficiently tied to the community, he took a reported $165,000-a-year position as the interim head of human resources for Baltimore City Public Schools.
Mckesson’s approach to education and his roots in the nonprofit Teach for America, which enlists young people for teaching posts, were also sometimes criticized. In 2016, Charles Cole III, an educator who has worked as a director for Teach for America, even penned an editorial for NBC News titled “Why Is DeRay Mckesson getting a bad rap on education?”
Baltimore City Public Schools’ CEO Sonja Santelisis defended him. “There is no way we would have made it through this first year without DeRay’s leadership,” Santelises told the Baltimore Sun. “He is leaving us in such a better position. He is one of the rare people who can talk about equity and then is not afraid to put boots to the ground and do the hard work that yields equity.”
He left that post in the summer of 2017 to concentrate on other activities, such as his podcast, “Pod Save the People.”
And Mckesson doesn’t rule out running for office again.
“I was in the school system for years. Nobody has to tell me about the importance of being on the inside,” he said. “I’m young. It’s not out of the question. The reason I live in Baltimore is that it’s a city I know, it’s a beautiful place and could be so much more if we had the leadership to get it up to its potential.” cary.darling@chron.com