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Author and activist DeRay Mckesson


DeRay Mckesson discusses his debut book “On the Other Side of Freedom: The Case for Hope.” He talks about his early days protesting on the streets of Ferguson, Missouri, and the figures who have inspired him to take action. Mckesson presents an intimate portrait of the Black Lives Matter movement from the front lines through personal memoir, and offers a meditation on politics, justice and freedom.

Josh Hamilton: I’m Josh Hamilton.

Joe Skinner: And I’m Joe Skinner.

Josh Hamilton: And this is the American Master Podcast, where we have conversations with the people who change us. Today, we talk to author and activist DeRay Mckesson.

DeRay Mckesson: We can win in our lifetime. Part of what we have to do as people who believe in a better world is that we have to fight for it and have the big dream. I worry sometimes that people only think about resistance as the teardown and not also the build-up. And if we tear down all the bad things in society that doesn’t mean that freedom just walks in, we actually have to build the stuff that we want.

Josh Hamilton: DeRay Mckesson hosts the podcast, Pod Save The People, a social justice news and politics interview show that covers topics such as voter suppression and police reform. Although Black Lives Matter is essentially a leaderless activist movement, Mckesson is often described as a key figure in the organization. He’s also the founder of Campaign Zero, a campaign focused on ending police violence. Joe had a chance to interview DeRay about his new book, “On The Other Side of Freedom: The Case For Hope.” Joe tell us about this.

Joe Skinner: Well, if you’re familiar with DeRay Mckesson, you would know that he was definitely wearing his famous blue vest for our interview. If you’re not familiar, the blue Patagonia vest is something DeRay wore when he first protested on the streets of Ferguson in 2014 following the fatal shooting of Michael Brown by police officer Darren Wilson. He cites the vest as a daily reminder of where the movement began and he’s worn it every day since. Including when he met with then-President Barack Obama at the White House. His debut book is an astonishing blend of autobiography and public policy opinion.

Josh Hamilton: Yeah, I love this interview. His mind moves at a mile a minute.

Joe Skinner: Yeah, one of the things I really appreciate about DeRay is this incredible ability to both beautifully articulate a problem and to always suggest potential solutions within the same breath.

Josh Hamilton: Let’s go to the interview.

Joe Skinner: Well thanks for coming DeRay.

DeRay Mckesson: It’s good to be here.

Joe Skinner: It’s intense to actually read your words in a book since I’m so used to seeing everything in short character limits.

DeRay Mckesson: It was intense to write in a book.

Joe Skinner: Yeah.

DeRay Mckesson: I’m so used to writing in short limits.

Joe Skinner: Why did you decide to write a book?

DeRay Mckesson: You know, so I wrote a book called “On the Other Side of Freedom” and in some of the why is I listened to this sermon not too long ago and the sermon was called “Don’t tell your story too soon”. And I remember being like, “Great title. Like I want to know what like what the what the message is and what he said it was like sometimes, “You can tell your story. So all you see is the pain not the purpose.” And if I written a book two years ago what had been like about the play by play of the sort of wildness of protest. And I got to a point a year ago when I was like, “Now I know the lessons. I get it.” Like I get like why we did these things what this meant so it’s a book of essays. It is both a reflection on where we’ve been and where we should go. You know I think about the essays that are more personal like I write about being gay. I’ve never written really about being gay. I write about my mother leaving and what it was like for her to come back and then I write about some of the research we’ve done about policing that we’ve never really put anywhere. I write about the protests and the first sort of long form thing I’ve ever written about them. So I think about it as like a meditation on the most important stories that I’ve been a part of and the most important experiences and then what those lessons were that I wanted to share with everybody.

Joe Skinner: And just people that might not be familiar with the work, how do you define yourself?

DeRay Mckesson: I define myself as a civil rights activist. I was one of the original protesters in Ferguson in August of 2014. I was one of many people who stood in the streets and used my platform online to help people all across the world understand what was happening about not only the death of Mike Brown but what was happening across the country. You know you think about what does it mean that we live in a country where a third of all the people killed by strangers are killed by a police officer and we think about issues of mass incarceration, the racial wealth gap. All of those things are things that I spend every day fighting to make sure that we bring equity and justice into the world and the fight continues.

Joe Skinner: You’ve written that Twitter saved lives. How has Twitter been an important platform for this work?

DeRay Mckesson: Yeah, you know in no uncertain terms if not for Twitter in August of 2014, Missouri would have convinced you that we didn’t exist. You know most people don’t realize that the first city that you saw aerial footage of the protest was actually Baltimore. Like you didn’t see it in St. Louis because there was a no-fly zone declared immediately over the entire region with regard to the protests so, you know if we hadn’t tweeted and taken Vines like you literally wouldn’t know any part of our story, our side of the story. You know back in 2014 there was no Twitter video. There was no Facebook Live. Literally it was Vine- like we would take a video on our phone. We go stand back off from where that whatever was happening and we’d like listen to the best 6 seconds and upload it- like that was what we were doing. It was very not high tech. And you know, you think about all those things it’s like we were able to push against a dominant culture and narrative. We were there to challenge mass media and all those things because We That Can Tweet. And that was really powerful for us. Twitter is like a little different today. You know it’s like a haven for white supremacists in some ways, in a way that it just wasn’t before. You know that just wasn’t a thing back then in that organized of a fashion. But I still believe in the platform. You know, I think about I’ve seen the best and worst of it is that the first person ever permanently banned from Twitter for anything was actually banned for trying to raise money to get me killed. So you know I take that personally. And then I see how incredible it was to like have all of our voices tell these stories that people tried to ignore. And I write about that a little bit in the book. I’ve always thought about Twitter as like the friend that’s always awake, which is a chapter in the book.

Joe Skinner: So in your book I know every chapter you kind of include quotes from great leaders of the past and the present. And I’m just curious if you could talk a little bit about the leaders of the past that you look to.

DeRay Mckesson: So many people you know I’m mindful that we exist in a legacy of struggle that we didn’t invent resistance in 2014 and we didn’t sort of discover injustice for the first time, right? That like those things existed before us. Well we had different that was really powerful was tools. I can speak to a million people at the drop of a hat in a way that they just couldn’t before. So the tools change the way that we engage in the work, but the work is fundamentally the same. You know I look to people like Bayard Rustin who was gay and was shunned in the civil rights movement because he was gay. You know you read his writings and it’s like very plain logical like this is why we did it. This is where people said. This is what people challenged. Like I think he’s underrated in this space. You know obviously Baldwin was a poet with the way he talked about race and justice. You know I think about people like Ella Fitzgerald. People like Diane Nash. Diane Nash trained the Freedom Riders. I remember meeting her and was like, “What was it like to train the freedom riders?” Right, like that’s such a- you know we think about all these young people getting those buses but not about like what it meant to train them and what that discipline looked like. So those are some of the people that I go to for inspiration who led before. Or like Bernard Lafayette. I’ve been reading him. He’s one of the first organizers in Selma and it was such a great story I asked him like how did you start organizing in Selma? He’s like, I was in Selma. And one night- he’s like first night and I was there. His car broke down. And these kids pushed his car like they came and helped him and they were the first kids that he organized and I love it. You know, it’s such a reminder that so often in this work it’s like the random encounters actually become these things that change people’s lives.

Joe Skinner: You write about Claudette Colvin – her involvement in Montgomery, and if you could speak a little bit about that historical erasure of those figures.

DeRay Mckesson: Yeah. So I went to Montgomery and what was sort of incredible about Montgomery is you can see the marker of where Rosa got on the bus and where she got off and it’s like you know she wasn’t- she was on the bus for like a hot minute. It was real quick. But Claudette Colvin was actually the first person to challenge and not get off the bus and like sort of push back against Montgomery bus company. But she was young, she was sort of like seen as feisty, wasn’t seen as like a good example or like a good face for that part of the movement. So Rosa Parks is who we know so I write about her when we think about it like all the people that have been forgotten when we think about civil rights work. I think about Joanne Robinson too who I also write about in the book is that I didn’t know until I went to Montgomery that the bus boycott was started by a professor who you know she saw what was happening. She got friends to like open up a space where she could make flyers essentially and she passed out like 50,000 flyers and like that is what started the bus boycott. It was like a person who believe that the world could be different and then organize people around her. And the narrative that we get told so often is like well the young King and all these people came in and they organized and like they definitely came and provided the infrastructure. But it was really the belief of one, two, three people, four people who like helped create a moment. When I think about Ferguson, what was so incredible about Ferguson and the movement that it birthed and the protests all across the country is that regular people who came outside was like this is not- we’re not going to let this go unnoticed. We’re not going to let people like act like this didn’t happen and we were in the street for 400 days. You know you think about what it meant to be in a place where like, it was illegal to stand still. If you saw us marching it wasn’t that marching was like some really cool thing to do in the middle of the street. It was like we had to. We literally couldn’t stand still or we were arrested if we sit still for more than five seconds and you think about all those things. So I wanted to use the book as a way to tell those stories too about the people like Mama Cat, Elizabeth Vega, people who you don’t know but if not for them there would be no protests all across the country. There would be no movement. There would be no moment at all.

Joe Skinner: Has the way that we recognize these figures changed in light of Twitter, and the way we tell these stories?

DeRay Mckesson: I think- I think some of it has. I think that they’re just- the gatekeepers are different, all of a sudden. That people can like, you know you can tweet something today and if it catches on it can be national news tomorrow. Like that’s just different. I do think that, this is something I didn’t appreciate until much later, is that there still is an access issue, so some of the narratives that become dominant narratives are because like you just knows- you know how to pitch something to a newspaper. You know how to write an article in a way. So you get these narratives that get seeded that aren’t necessarily true but people have access to, like platforms. And I think that that is still hard. You know it’s hard to think about all the sacrifices that everybody made who was in the street in Ferguson for a very long time. And you really don’t know their stories, right? Like that’s just not- you know a couple of us but there are so many more people who did incredible work and we should talk about that, right? We should talk about what it is like to- you know there was a bail fund, and there were people that led the bail fund and there were people who planned these incredible actions that like really were you know, we didn’t know we were going to be right in it and we knew we were in the right side of justice but we didn’t know that the country would rally behind us. But people planned in the midst of it anyway. And they did incredible things. People who I would risk my life with. Over and over again. And we should tell those stories. That is a part of the way erasure works too is that we can think about collective storytelling and not only focus on one or two, or this- these myths of founding and things like that.

Joe Skinner: And James Baldwin writes about changing the idea of power itself and the idea of domination itself. You write about that too.

DeRay Mckesson: Yeah, you know Baldwin has so many gems that people have obviously seen, but he has this great quote that’s like, “Whiteness is a metaphor for power.” And you know what he’s saying in that moment is this notion of like whiteness is synonymous with domination, that what happens when you have a country sort of rooted- and not even sort of- rooted in white supremacy, that that creates a dominant culture that necessarily has those vestiges. And part of what we have to do is recognize those vestiges and undo the damage that they’ve done and we think about this distinction that these great organizers came up with. That is like the difference between power over and power with and domination is about power over. This idea that there’s a finite set of resources and things out there and that my goal is always to get more than you. Like that is sort of what we have. It’s like power is like a pizza pie. And like I want as many slices as possible. But we want to build a world that is about power with. This idea that like, power is actually infinite and expansive and we both gain when we gain. That like we can actually build something together better then we can build apart. And it’s not about you having more me having less. It’s about both of us having what we need and we think about things like the difference between equality and equity, right? Equality is everybody gets the same thing. Equity is that people get what they need and deserve. And we wanted to live in a world of equity, right? We’re not asking for equal funding for school systems, we’re asking for equitable funding. We know that it costs more to educate kids in poverty. To educate kids from low incomes and we want to make sure that they have the resources to get what they need. And you can’t get to equality without the equity issue first. And like Baldwin helps us enter into those conversations.

Joe Skinner: I feel like education is such an important part of your background and the way that you present your ideas. Could you talk a little bit about how you worked in education before getting into activism?

DeRay Mckesson: Yeah, teaching is like the best thing I’ve ever done. You know it is. I taught sixth grade math- sixth graders are adorable and amazing and smart and like they’re old enough. I taught math, so they’re old enough that they can do complicated math. You know we can do, my second year I taught essentially sixth through eleventh grade algebra to my sixth graders and they could do like the most complicated factoring polynomials with the best of them. They just like could do it. They’re old enough to do it. But they’re young enough to still believe in magic. And I can walk in every day and be like, “We are math magicians!” and they would be like, “Yea!” and I’m like “Yea!” And you know like, seventh graders won’t do that, but like sixth graders are like damn, you know? Seventh grade is puberty and deodorant and it is rough. But sixth grade is like still a lot of joy. So I taught and that was incredible. I helped lead the largest community center at the Harlem Children’s Zone up at 145th and Douglas, went back home opened up an after school center for middle grade, so the center was fifth through eighth graders. And then I trained and supported a third of all the new teachers in the city of Baltimore, worked in the office of human capital trying to think about like how do we make sure all the adults who are around kids are the best adults possible. I ran for mayor and then I most recently was a Chief of Human Capital on the school system in Baltimore leading that work. And the youngest chief in the history of the school system and it was, it was incredible. It’s like such a- public education, I think is, is- we obviously all think it’s important, but when you work on the inside you’re like, “we have such a responsibility to do this right.” And it’s part of the reason why I think about a book rooted in hope, right? When I think about the title “On the Other Side of Freedom”, it’s like how do we get there? Like what does that mean? I believe that how we get there is a focus on structures and systems and doing that. But also this idea of the case for hope is that hope is our belief that our tomorrows can be better than our todays and that to me was born both in the streets and in the classroom. That like you look at these amazing 11 year olds and you’re like, “Everything is yours!”. I went to get a cupcake in SoHo not too long ago and I walk in and it is a kid that I taught! And I’m like, “Jeremy! Oh my god I know you!” You know, he’s old now, he’s like 21. But I taught a decade ago which is sort of also a lot. But on the first day of school he walks up to me and he, I’ll never forget it, we’re in the playground. And like you know, they’re sixth graders so it’s like new school to them. And he’s like, “Are you going to be my teacher?” And I was like, “Yes”. And I saw him at the cupcake shop. And I’m like, “Jeremy, are you still friends with like, the kid he was with?” And, yeah they grow up. Kids are a special joy you know.

Joe Skinner: What would you say to a young kid today that’s looking to get involved?

DeRay Mckesson: So many things. And the last chapter in the book is called “A Letter to an Activist.” And I wanted to, you know I think about this notion in “On the Other Side of Freedom” is that there’s a question about like what is on this side of freedom and then like how do we get to the other side? And when I wrote the chapter “The Letter to an Activist,” it was like, what’s my advice to people? And I think that you know I talk about a lot of things but some of it is like, find an issue that you care about and learn it well- that like you need to know one thing well that will actually open up your eyes so that you can think about how this was created, like that whole piece. The second is know that you have more power than anybody will ever try to tell you or like will help you understand that part of what was the beauty of the protest and continues to be is that there are all these people who have found their voice when they didn’t think they had one. So like I can think about all the times I’ve been in the street. And there are these young people or old people who have never imagined that somebody will listen to them. It’s like, “you can do it.” Like this is yours, like let’s do it and part of what I think the magic of Ferguson is in the first wave of the protests was is that all of us we just walked into the risk. Right? Like we had no reason to believe that we would win and that people would listen but we walked into the risk anyway and like that would be my advice to people today is like walk into the risk and the last thing I’ll say is you know we can we can win in our lifetime. That there are people- a part of this is a belief that we’re laying the foundation for the next people and all this and I believe that. But when you think about like if they can rewrite the tax code on the back of paper towels and napkins and it’s like the biggest rewrite of the tax code in the last hundred years or something wild. Then like we can actually undo this stuff pretty quickly too. Like it’s never a matter of like “can we?” It’s always a matter of will. And part of what we have to do is we will believe in a better world. We have to like fight for it and have the big dream and that the difference between the right and the left with regard to the messaging and imagination is that the right is trying to bring back a time that we’ve already survived. It’s deeply rooted in nostalgia and that’s not hard. It’s like there’s no new imagery they have to do that just like referencing all this stuff. On the left, we’ve never seen the world we are fighting for. This is all make believe. You know it’s like a world where every kid can read, we don’t know how that looks like. A world where every kid has breakfast, lunch, and dinner. I don’t know, like a world where the police don’t kill people. Never seen it. Right, so we’re always trying to make something up which is like the hard part of- we have the burden of imagination and part of what that means is that we have to keep at it. Even when it seems hard and futile and it seems ridiculous. You know 100 years ago we were like cutting people’s wrists and draining their blood and we were like, “That’s health care.” It’s like that didn’t really work. So we’d imagine like new ways of being a community around medicine and like we have to keep imagining new ways of being a community around safety and education and like we- I think I worry sometimes that people only think about resistance as like the tear down and not also the buildup. And if we teared down all the bad things in society that doesn’t mean that freedom just walks in. We actually have to build the stuff that we want.

Joe Skinner: I took a lot from your book when you talk about imagination verse nostalgia and that really rang true. I feel like there’s not a lot of room for imagining in adult life in this country in a lot of ways.

DeRay Mckesson: Yeah, and we’ll never win if we don’t imagine- well like we’ll never win if people haven’t grappled with things like, what’s the type of classroom you want to put your kid in? You know, like what would make you feel safe in a community? Like all these questions that are like basic questions that people often don’t feel equipped to talk about because they think that there’s like some policy-makers somewhere who has the insight- I’ve been in a lot of rooms with these people. They don’t have any answer. They’re like making it up too, you know what I mean? So when we say that- when we say something like the system is broken and people say, “Well, it was designed to be that way.” My takeaway is that it was designed, right? Somebody made this up and you can be the somebody and we can make up something much better than this.

Joe Skinner: Right. We’re all humans and these are all kinds of just structures that we’ve invented on our own.

DeRay Mckesson: Yeah. Like what is theft? It’s like somebody made that up, you know like what does it mean to be separated from society? That doesn’t have to look like what we think of prisons like today. You know if people have done things, I mean they need to be separated from society, we should have a conversation about what does separation look like, you know people ask me all the time because I spend so much of my work on the police they ask me like, “Are you saying the police should never kill people?” And it’s like… Well tell me when the police should be able to kill your child, you know? Like we should… we should grapple with these sort of questions.

Joe Skinner: And do you think that change should happen through incrementalism or through radical change?

DeRay Mckesson: I don’t know if it’s radical to say that we can feed every single kid every day. Right, like that is a part of this is pushing back on the notion that like the things that we ask for are radical, and the radical part is that we have to ask for them in the first place, right? I think it’s actually like a pretty basic idea that like every kid can read and write and we should start talking about it as a basic idea. You know we should- this idea that that we can have safe communities that aren’t predicated on the police killing people is not radical… That seems like pretty basic to me. So I think that the things we’re actually fighting for are pretty- not dramatic. You know part of the drama is that we have to fight for them. But I think the thrust of your question is like, “Can we get the wholesale change soon?” Yes. I think we can. But it is- some of it is rejecting this idea of like, radical or like extreme, because we know that polarization thrives in a world of extremes. And like the people we’re fighting against are extreme. Like the people who push back against the notion that like we can feed every kid every day. That is an extreme. That’s extreme. You’re like that is, we have no food and there’s not like a food shortage, you know what I mean? Like we can actually do that. I’m from Baltimore. I live in Baltimore. And you know when I was the Chief in Human Capital we thought that we were going have to lay off 1000 people because the school system didn’t have enough money and come to find out the state has a surplus of 500 million dollars. It’s like you actually chose not to fund public education. It’s not like there is no money, you know what I mean? And like it’s not extreme to think that you know, in Baltimore literally 60 schools had to close recently early because of extreme heat and you’re like we figured out the air conditioning thing like 100 years ago. You know and part of what we have to do when we imagine is talk about it as simply and as basic as the reality is. Like we can clothe every kid, everybody can like eat every night. You know, this stuff is actually pretty basic.

Joe Skinner: How can a white listener be an ally, or as you write be an accomplice to the cause?

DeRay Mckesson: Yes, when I think about people, you know, there’s a part of this about how to- how do we identify ourselves as activists, organizers, that sort of. And I’m less interested in those macro labels and more interested in the work you do, right? So there are people who call themselves activists who aren’t active in any way, there are people who call themselves organizers who question what they organize. I’m interested in the work people do- so you don’t need to. You don’t need to identify as an activist to do really incredible work, right? And like I know that and I also know that some of the best organizing started because like you and your cousin and your next door neighbor like sat in a living room and were like, “I think this thing doesn’t make sense. I’m gonna see what I can do.” And like that’s actually like how all of the stuff that you think is incredible and transformative, it started with those sort of nuggets, you never see those. Like you see me now like a million followers and you didn’t see me sleeping on the side of- like in a van on the side of the road after the protests in the middle of the night, like you didn’t see those moments but those are the things that built this, built so much of what we recognize today. This question about whiteness. You know when I think about the best white allies and accomplices we think about allies as people who have an understanding of injustice and systemic injustice at a basic level. They sort of love you from a distance. They’re like, “I agree with you. Go ahead and flight. I’m here.” Accomplices are people who love you up close. They say like, “I agree with you and I’m ready to be in the fight with you. And I’m ready to put something online to make sure we do this work well.” You know I think for white people it starts with the recognition of privilege in the way that whiteness works. That you don’t have to have been an impetus for creating the conditions of injustice to benefit from them. So when we think about like how whiteness sort of, you think about things like wealth, the wealth gap in 2033 is going to be the biggest gap that we have since we started recording wealth. The median wealth of black people is projected to be zero dollars, which is sort of wild. You think about how white wealth was built. It wasn’t like all white people just like worked really hard over the last I don’t know- two, three centuries. It was that we literally created a condition where we gave white people wealth. We gave white people like housing loans for almost nothing. We gave people- white people education and didn’t give it to other people, you know, like the history of Jim Crow and slavery like all those things were like how we build wealth for white people and like we can acknowledge that and like white people benefit, all white people benefit from the way that we built wealth. So people should acknowledge that that happened and think about like how we actually write the system so that everybody has a piece of the pie, that again we don’t think about the pie as a zero sum space. We think about the pie as a space where everybody can win. So allies are people who have like that basic recognition, haven’t yet linked it back to a system that created these conditions and aren’t yet ready to be in the fight themselves, accomplices are people who like understand all of that. When I think about what people can do it is white people specifically can recognize like how they benefit from the system and then think about like what are the structural pieces so we think about again, wealth it is an interesting one. You think about mass incarceration. I think about all the protests I’ve been to where white people can challenge the police or white people when they say it, people are like, “Oh my goodness this is incredible!” And you’re like, “Black people have been saying that for a long time.” So there’s a whole chapter in the book on “The Other Side of Freedom” that is called “The Choreography of Whiteness”. It’s like understanding of the way whiteness works. And like how we can actually do our own work to dismantle the way that white supremacy has taken hold in culture.

Joe Skinner: Just to bring it back a little bit to the arts, you write about Aretha Franklin and how she- I hate paraphrasing this but I think you said something along the lines of we need to use our gifts to make a space for each other. I guess I’m wondering if you could talk a little bit about how somebody in the arts can or has created a space.

DeRay Mckesson: So many people- I think about when I first met Beyonce. You know, her- I remember meeting her in the office and it was a year before “Lemonade” came out. And I remember sort of thinking about the album and her commitment to black people and her commitment to using her platform to like, literally create space in the most public way for these conversations. Like using art as like a window and a mirror and it’s like there’s no better example than her. I think about Solange and when I got arrested in Baton Rouge, Solange and Alan, her husband, they were both there when I got out. And like you know, that was also before the album came out, I think. And you know our conversations about like how she thinks of herself as an artist and what that means and as a black woman and like how she uses her platforms and I think about both of them obviously incredible artists and sisters as like really great examples of what it means to use art to do work. Like not just to entertain but actually push conversation and like open up space for people. I talk about this notion as like protest is the idea of telling the truth in public, right? And some of our best artists have been using their platforms to tell the truth in public.

Joe Skinner: Well I really appreciate the way that you consistently in everything I’ve read offer answers to a lot of the problems that are presented and I feel like it’s just a really generous text in that way. So, so I say thanks for that. And also thanks for waking up super early and coming in here.

DeRay Mckesson: No, I appreciate it. Great to be here.

Josh Hamilton: From the American Masters Digital Archive, the poet Dr. Maya Angelou.

Dr. Maya Angelou: From Nelson Mandela to Robert Sobukwe, Martin Luther King’s movement inspired them in the late 50’s. Because as we, African-Americans, have moved forward toward freedom and fair play and equality, so other people have been moved. It was of interest for me to see when Marcos went down, the song that was sung in the Philippines was “We Shall Overcome.” It is of interest to see in Poland people moved to rid themselves of colonialism, of the Soviet Union, that people sang “We Shall Overcome.” It is no small matter, a chance to see that human beings were more alike than we are unalike.


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