Issac Bailey, Author

I was first introduced to Issac Bailey at the Chicago Tribune Printers Row Lit Fest last June, where he spoke about his book My Brother Moochie: Regaining Dignity in the Face of Crime, Poverty, and Racism in the American South. My Brother Moochie is a powerful, personal exploration of race and racism and of the impact on a family when one of its own serves a life-sentence for murder. In Moochie, Bailey addresses the issues of shame and isolation. In addition to having brothers who have spent significant time in prison, Bailey has a severe stutter, which he says has proved to have a greater impact of his life’s trajectory than his race.

My Brother Moochie is not an easy read as Bailey challenges his readers to look at issues from many different angles and to examine their own biases about race, poverty, and crime. Bailey examines shame and marginalization through a personal and historical lens; he asks questions and, with brutal honesty, shares his own struggles growing up and as an adult raising children in a less-than-perfect world.

Bailey spent his childhood roughly thirty-five miles north of Charleston, South Carolina, the fifth of eleven kids. He began his journalism career with The Sun News in Myrtle Beach, where he started as a part-time reporter and calendar clerk before taking on various positions, including feature writer, real estate reporter, business editor, blogger, and the paper’s primary columnist. His investigative reporting led to policy and legal reforms within the South Carolina Department of Social Services and was instrumental in changing how the agency handles child protective services cases.

Bailey was a 2014 Nieman Fellow at Harvard University and has been published by several dozen publications, including Time magazine, Politico magazine, Esquire online,, The Washington Post, and He is currently an editor-at-large for and will be teaching journalism courses at Davidson College in North Carolina in the fall. He is working on his third book, A Black Man in Trumpland: Why We Didn’t Riot – But Should Have, which “concerns why black people are angry in the age of Trump.”

I had the great pleasure and honor of interviewing Issac Bailey over the phone in October 2018.

Diane Gottlieb: Good morning, Issac. I loved hearing you speak in Chicago and it was a pleasure talking to you at the book signing. I have to tell you that My Brother Moochie just blew me away.

Issac Bailey: Oh, wow. Thank you very much.

DG: It really did. I’d like to start where you start in the book. You begin with a pretty intense interaction you had with your own son when he was thirteen. You were angrier than you later thought you needed to be, and you relate your feelings to the particular struggle that black parents have raising black sons. This topic’s been covered before by Ta-Nehisi Coates, for example. It’s that fear for their black bodies out into the larger world. But you also added a whole other layer to the discussion. And that’s what I appreciate so much about your book and your articles. You add these really difficult, complex layers. And in this case, it’s the layer of shame.

IB: That’s right.

DG: Yes. So, if you could just say a little bit about how you see the unique intersection of fear and shame when it comes to parenting a child or teen of color?

IB: Yes. Actually, the hardest thing about trying to parent is that you’re not just parenting your own kids. You are also trying to prove how people who look like you are worthy as human beings. It’s like that at least for me. I’ve actually become too afraid for my kids. So now, I’m trying to be really aware of that.

DG: I read your article about you not giving them “the talk” about how to respond if they’re ever approached or pulled over by the police.

IB: Yes, exactly.

DG: That balance, I think, that every black parent has to carry is enormous.

IB: Oh yes. Yes. And so, at least for me, one of the reasons I don’t give that talk is simply because I think that that burden should be placed on the person who actually has the most power in the situation. In this case, that’s not my son. It’s the cop. I want cops to be held more accountable during these situations.

DG: I have a question about police accountability. What do you think about the verdict in the Jason Van Dyke case?

IB: I actually thought, finally, something wonderful is happening because the jury didn’t just simply buy his story. The cop said that he felt scared and then because of that it was actually okay to murder someone. The jury didn’t buy it.

DG: Do you see this is as maybe a tipping point or a turning point?

IB: I am hopeful that it is. But I’m not sure. There were two other cases like this in Texas this year where we also saw guilty verdicts. Yes. So hopefully, this is a start of something new, yes.

DG: We need some new starts.

IB: Yes, exactly.

One major thing is that I try to tell uncomfortable truths while not giving any fodder to racial stereotypes. That is a really delicate dance.

DG: Back to the book. I see shame as being at the heart of the book, just as it is in many, many problems in life. And the pain that shame causes. It’s palpable.

IB: Exactly.

DG: And what really interested me was when you said that your family, and families of perpetrators of violence in general, are the “black sheep of the black sheep.” Could you talk more about what it was like to have no space for your family’s grief and trauma? And about the burden of being the black sheep of the black sheep?

IB: Yes. Essentially, it is one of the most suffocating feelings that you can have because there is no place to turn. Even your friends and your neighbors have to keep you at arm’s length because if they get too close to you, they, too, will have to carry the extra burden. One of the most devastating parts about it is that it forces you into silence. And that makes it impossible to really grapple with everything that actually happened and to get help when you really, really need it. You have this trauma that will manifest itself later on in various ways.

DG: Was this an internalized understanding that there was no place to go? Or did you try to get help and were shut down?

IB: I think that it was more of an understanding. But I know that my mom had tried to get help. One of our neighbors was a state representative, and my mom went to him and asked him to say something positive, anything positive, about Moochie to the prosecutor or write a letter to the judge, for instance. But he said no. He turned her down.

DG: He said no?

IB: Yes, exactly. That was the typical response, yes.

DG: Oh, wow. That was probably up there—almost as hard as facing the actual event.

IB: Yes, exactly. That’s for sure.

DG: Another part that really, really moved me in the book was how you described the challenge of balancing your love for Moochie and for your younger brothers with the hate for what they did. That balance of holding the history of racial inequality and violence against blacks along with the fact that your brother actually killed somebody. Could you talk a little bit about that balance, about what you call your “schizophrenic endeavor?”

IB: Yes, yes.

DG: I love that—”schizophrenic endeavor.” Because how else can you describe it?

IB: Yes, yes, that’s for sure. I love my brothers, but at the same time, there were periods where they actually felt like a danger to my family and the town of St. Stephen. We could not get them to stop, to change. It was extremely frustrating. I felt helpless. There I was, trying to love them, but also recognizing the fact that they were real dangers to people that I also loved.

And then there’s also all the reading and research I’ve done on racial history. I mean, especially when it comes to, say, maybe somebody like Thomas Jefferson, for instance. There does not seem to be any real struggle, at least for many white people, to try to honor the good things he did and also to grapple with all the awful things that he did.

DG: Right.

IB: Yes. It seems as though that kind of struggle is a bigger deal for black people. And I’m not sure why.

DG: You know, it reminds me of the first question, of carrying the shame. I loved when you said in your book that white people don’t seem to question why it’s only white kids that go in and shoot up schools and movie theaters. And, you know, I always say, “Ah, another white kid. Another white boy.” And I really can relate to the feelings that people carry. Like when there’s a mass shooting. I can just imagine Muslim Americans saying, “Please, please not. Please don’t let it be a Muslim.”

IB: Exactly. Exactly.

DG: I’m Jewish. And I remember when the Bernie Madoff thing came out. And, I remember saying, “Oh no, please. Anything having to do with money, please don’t let it be someone Jewish.” You know?

IB: Of course.

DG: And it’s this shame that you carry for the stereotypes people have of you, whoever you are.

IB: Exactly. Exactly.

DG: But white people who are not in these other groups don’t carry that shame. When a white person commits an atrocity, everybody’s suddenly an individual. They just say, “well that’s not me. It’s got nothing to do with me.”

IB: I know, exactly. I know, right? Exactly. Then it’s just, “We’re all individuals.”

DG: Right. Okay. So, while I was reading Moochie, I thought—on many occasions—this guy’s going to offend everyone! You just challenge all sides, all views, biases, all assumptions with equal zest. And I know from reading several of your articles that you’ve gotten pushback from all sides. It doesn’t seem to bother you too much, or at least it doesn’t stop you. What have been your greatest challenges when writing about race?

IB: Oh, yes. One major thing is that I try to tell uncomfortable truths while not giving any fodder to racial stereotypes. That is a really delicate dance.

DG: It is.

IB: Especially when you’re writing about crime and black men. That’s my biggest struggle. I’m always trying to find that sweet spot, that most honest place.

DG: That is really a struggle, right?

IB: Oh, yes. Massive struggle. Yes. That is my top struggle, that is for sure.

DG: And you know you’re going to hear about it later.

IB: Yes, exactly. Exactly. Yes.

DG: So, we can’t talk about race in our country without bringing up the criminal justice system.

IB: That’s right.

DG: There definitely has been movement in the right direction. But mostly for non-violent drug offenders.

IB: Exactly. Exactly.

DG: I love how you even question that. You just get in so deep and bring up ways of thinking about issues that most people haven’t considered. For example, when you said that drug trafficking is not a non-violent offense.

IB: Exactly, it’s not.

DG: Because it is a violence. And whether this guy shot somebody or not, he’s engaging in violence by trafficking drugs. There is extreme marginalization of violent offenders, and their needs must to be considered in the prison reform movement too. Can you tell me what that would look like for you?

IB: That is a great question. A first step would be a philosophical recognition that we are not the worst thing that we’ve done. In practical terms, we need to look at our history going back to the 1950s and ‘60s, for instance. Even when people did something violent, we did not automatically give them really, really long sentences. If we can get back to some of that, well, I think that would go a long way.

DG: The acknowledgement piece, though. I just don’t see that around the corner, you know? People are so afraid.

IB: Exactly.

It seems as though many people are actually trying to understand when it comes to race and ripples of trauma. Since the book has come out, I’ve had more opportunities to fully explain myself and what families like mine go through. And that’s been very helpful.

DG: People see others who have committed violence and say, “Oh no, they’re not me.” And what struck me is that through your own experiences with PTSD, you’ve debunked that statement. It could be me. It very well could be me. There, by the grace of God, go I.

So, here’s another thing you said in the book that’s really interesting,” My brother is a murderer or at least a man who committed a murder.” And, to me, that’s a really important distinction. It’s not just a matter of semantics. It’s a whole different perspective. And do you have that perspective?

IB: Like?

DG: Like, do you sometimes see him as a murderer? Or do you see him as a man who committed a murder?

IB: I’ve actually gone back and forth on that. That, too, was part of my struggle for many years. When I was in college, I actually did not mention his name once. I saw him as a murderer because I knew that’s how that he was viewed. I’m stronger now and much clearer. I definitely don’t see him that way anymore.

DG: But it was a process.

IB: Oh yes. A long process. That was a years-long process, yes. For sure. It definitely was.

DG: Has writing the book helped you to heal some of the shame?

IB: Yes. It seems as though many people are actually trying to understand when it comes to race and ripples of trauma. Since the book has come out, I’ve had more opportunities to fully explain myself and what families like mine go through. And that’s been very helpful.

DG: So, I think part of this shame thing is the invisibility. Shame makes you want to hide. For a lot of people, though, invisibility is not a choice. It’s forced on them.

IB: Exactly.

DG: Like, when Moochie was put in solitary confinement for not cutting his hair.

IB: Exactly.

DG: Do you feel that writing and putting these things out in the open has helped to alleviate the shame? Is that part of it? Becoming visible about it?

IB: Yes. And the biggest part about it is that you actually feel less of a need to hide. It’s been this massive relief.

DG: How else has the process of writing this personal—deeply personal—account changed you?

IB: One of the biggest changes is that I’m now more open with my wife. And when I catch myself trying to retreat emotionally, I am actually able to stop myself from doing that.

DG: That’s great. That’s wonderful. So, she probably wants you to write more books!

IB: Yes, exactly. Exactly.

DG: Has Moochie read it?

IB: Yes.

DG: And what was his response?

IB: Well, he’s been happy about it simply because he thinks that it has given him voice again.

DG: That’s great. So that’s been healing for your family, too.

IB: Yes, yes. It’s been a process, for sure, yes.

DG: One of the gifts that I feel I got from reading Moochie is that it introduced me to your larger body of work in journalism. I love how you challenge yourself and your readers!

Because, at least for me, hope actually comes through tensions and struggle and from people embracing that tension and struggle. I think that’s when real progress is going to come.

IB: Thank you.

DG: And you have no problem calling anybody out. You write a lot about race and about writing about race. In one article “Don’t Shy Away from Dealing Forthrightly with Race,” you mention Dina Temple-Raston and Matt Taibbi. Both are white and both have written important books that deal with race. Any thoughts or advice for people who want to venture into this territory?

IB: Oh, yes. Yes. At least my views on this are pretty basic. Just as long as it’s a worthy story told well. As long as that’s the case, then I think that nothing else really matters.

DG: I’m with you. Aren’t we here to learn from other people and from their experiences? Otherwise, we’re just stuck with our own boring selves.

IB: Exactly.

DG: You’ve stated that murder made you a journalist, right?

IB: Yes.

DG: But how has journalism informed your memoir?

IB: It gave me the skills to get as close to the truth as possible.

DG: So, we should all do some journalistic reporting, right?

IB: Yes. Yes, exactly.

DG: What did you find were some of the differences in approach—writing a memoir as opposed to writing journalism.

IB: I think the transition was easier for me because I had already been doing column writing, which is shorter journalistic memoir, essentially.

DG: That makes sense. I loved your article in which you talked about the Clinton emails and how the media handled that. Have the media learned anything?

IB: I’m not too sure. I’m not too sure. I still think they are trying too hard not to be labeled biased. And, therefore, sometimes the truth takes a back seat. I think that that’s one of our biggest issues.

DG: It certainly is. You also talk about disappointments like Harvard and Michelle Jones and Trump’s election. Are you at all hopeful?

IB: I’m not sure that I am right now. Because, at least for me, hope actually comes through tensions and struggle and from people embracing that tension and struggle. I think that’s when real progress is going to come.

DG: Yes, and nobody’s doing that now.

IB: Yes, yes.

DG: How do you think race and gender are going to play into the next presidential election? Because we hear Elizabeth Warren called Pocahontas and with Kamala Harris and Cory Booker as contenders, do you think things are going to get even uglier?

IB: The ugliness will definitely still be here in 2020. But I think it will make it very difficult for him [Trump] to win.

DG: Because people will be sick of the ugliness, you mean?

IB: Yes. Yes.

DG: Oh! From your mouth to God’s ears!

It was interesting how you weaved your stuttering into the book. And how you feel that you could’ve been where your brother is, but in some ways, your stutter protected you from that path. At the same time, you say that your stutter has had a greater impact on your life’s trajectory than your being a black male, that it held you back in your journalism career. Can you touch on this?

IB: Yes. Having a severe stutter has been like nothing else that I have ever experienced. We only make up one percent of the population. At least with race, there are some people trying to understand.

But yet, with the stutter, most people don’t actually try to understand. The stutter isolates you even more. When it comes to my career, I’ve actually missed out on many more opportunities because of my stutter than my face.

DG: I’m sitting here, six degrees of separation from Barack Obama because you interviewed him. I can’t not ask you about that.

IB: Well, he did not seem to be bothered at all by my stutter.

DG: Yes, I read that in the book. I’m not surprised. Were you nervous about that?

IB: I guess that nervous is not the right word.

DG: Okay. What would it be?

IB: I always have to plan ahead. For any interview. Because I simply don’t know how difficult my stutter will be that day.

DG: Do you get star-struck?

IB: No. I guess that’s one of the blessings or curses of stuttering. I actually have had to wear blinders of sorts. Therefore, I don’t respond to such things like most people do.

DG: How is Moochie these days?

IB: Well, he’s getting better day by day. He’s actually been out for about four years now. He is still adjusting to this new world, of course.

DG: Sure. Has he gotten help for his PTSD?

IB: Yes, he has been seeing a counselor.

DG: Good. What’s next for you?

IB: What’s next? That’s a good question. I actually love teaching. So, I’m probably going to do that again next year.

DG: Great. And would it be journalism? Is that what you teach?

IB: Yes. I teach journalism and ethics.

DG: Ethics? I can’t think of a better person.

IB: Wow. Thanks very much.

DG: So, I have nothing else right now. I just want to say what a joy this was.

IB: Oh, wow. Thank you very much.

DG: Issac, I feel like I’ve made a friend.


Diane Gottlieb writes fiction and nonfiction is currently working on a murder mystery with a social justice bent. She is an MFA candidate at Antioch University Los Angeles and is the lead editor of creative nonfiction and a member of the interview team for Lunch Ticket. Her work has appeared in Panoply and Lunch Ticket. You can also find her weekly musings at