Love is the Why

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DeRay Mckesson and TeRay Ross are world-class community leaders, siblings, and the best of friends. They also grew up surrounded by addiction in both their immediate and extended family. As a result, they spent lots of time as kids hanging out in the back of 12 step meetings, absorbing lessons that continue to impact them as adults. This week, we sit down with DeRay, TeRay, and their dad, Calvin, to talk about how their understanding of addiction has evolved over the years and how they continue to support each other to this day. 


[00:02] Stephanie Wittels Wachs: OK! So I am so excited to talk to both of you together. Siblings are my favorite relationship in the world. So to start out, can you tell me what your age difference is?


[00:18] TeRay Ross: We’re about 18 months, right? 


[00:22] TeRay’s like a year-and-a-half older than me, depending on — I mean, always year and a half older, but sometimes we are only a year apart.


[00:33] TeRay Ross: No, that doesn’t change. 


[00:35] DeRay Mckesson: So anyway. See, I’m 34 now, and you’re — 


[00:44] TeRay Ross: I’m 35, I’ll be 36 this week. 


[00:54] DeRay Mckesson: See, and then we’ll be more than a year apart. 


[00:58] Stephanie Wittels Wachs: I’m Stephanie Wittels Wachs. I will be 39 tomorrow. And this is Last Day. 


[01:19] Stephanie Wittels Wachs: This sibling dynamic is so good and it’s so familiar to me. I mean, it’s such a specific kind of needling. You can torture your sibling like no one else in the world. This is undeniably true. And this is the relationship I had with my brother Harris. We totally understood how to lift each other up and how to tear each other down. So when I meet people who have that kind of bond with their sibling, it’s hard not to feel a little jealous, because I miss this so much. But it’s also kind of wonderful to experience it even by proxy for a moment, which is why I was so excited to sit down with this brother-sister duo. If you don’t recognize the voice of award-winning activist superstar DeRay Mckesson, you would definitely recognize his iconic blue vest. The other voice, the one who is trying to explain to him how time works, is his equally impressive older sister, TeRay.


[02:29] Stephanie Wittels Wachs: So what are your early memories? Do you have anything that vividly kind of pops out when you think about being little kids in the same house?


[02:39] TeRay Ross: So when DeRay used to get mad, he would put his head down and run at you. And that is like one of the things that I think of all the time and I think about us being little together.


[02:53] DeRay Mckesson: But TeRay was bigger than me, so I had to figure out something, because she was an athlete and I was scrawny. But my head was strong. What else about childhood? We spent a lot of time at our grandmother’s house, so we spent a lot of time over there, and our cousins lived in the two houses next door. And we spent a lot of time as kids with them.


[03:16] Stephanie Wittels Wachs: As kids, they spent a lot of time at their grandma’s house because their dad worked as a truck driver and their mom wasn’t around for other reasons.


[03:27] TeRay Ross: So my mom left early. Like we were like three, four when she left. And we always knew that she was sick, or I understood it as her being sick. And my dad was around, but we just didn’t really talk about why when we were that little. So it was just pretty much she was gone, and because she was gone, my great-grandma had to live with us because my dad had to work and a grown-up had to be there. So for us, that was Nanny. But I don’t think that we really started having those conversations, or I didn’t really understand why until we were old enough to visit with her.


[04:08] Stephanie Wittels Wachs: When you’re a kid, you understand sickness as your head is hot or your nose is runny. It’s something that doesn’t feel good for a little bit. But with a couple days off school and excessive time in front of the TV, it eventually goes away and we get back to normal. That is what being sick looks like to a 3 or 4 year old. So to be that age, and to know that your mom is sick, your only real option is to wait for her to get better. And when that sickness is addiction, the wait is long. Maybe forever. And filled with lots of pain and uncertainty and confusion. 


[04:53] TeRay Ross: I think it’s easy for people to kind of hear that we had this jacked-up experience, but she’s an elementary school principal and he’s DeRay at So like but we still have these people that we love and like, we’re still impacted. There’s not enough money in the world that’s going to shield you from this coming to your doorstep. 


[05:13] Stephanie Wittels Wachs: Yeah, so it’s interesting, we had this guest last week, his name is Dr. Gabor Maté, and he’s this amazing doctor who has done a lot of work around trauma and the relationship of trauma to addiction. And he said no two children have the same parents and no two children grew up in the same family. And I was like — 


[05:34] DeRay Mckesson: TeRay — if only y’all could see — so here’s the thing. Let me just say, my great-grandmother helped raise us, and my great-grandmother was very nice to me and pretty evil to TeRay. So we talk about childhood and it’s pretty hard because I have all these fond memories. I mean, I was there, so I have fond memories of her treating me nice. And I remember her treating TeRay really awful. But yeah, we definitely had to — our father was fine with — he was the same for both of us. Adorable and ridiculous and only made one meal a week and stuff like that. Like one meal for the week. But Nanny was definitely different to us. 


[06:13] TeRay Ross: Yeah. She was mean, she was hateful. She did not like me. And like, again, I’m a grown-up now and I get it, she was born in the ‘20s and she had these very, you know, strict ideals of what a little girl should be. And I did not fall anywhere within what that was supposed to be, and I caught it for it. And I think about that in relation to my mom a lot, because I struggled with, you know, well, if she was here, if my mother was here, this evil, hateful woman would not have to be here, and I would not have to have these experiences. So, like I know we’re talking about, you know, the impact of addiction or in the larger family, and it took my mom away. And also brought this mean person in that place. And so I struggled. I struggled a lot with compassion and empathy for Joan because all of this was her fault as I saw it. 


[07:10] Stephanie Wittels Wachs: But Joan wasn’t the only one in the family using drugs. 


[07:14] Calvin Mckesson: I was 24 when I had my first child. That was TeRay. And DeRay came a year and a half later. And at that time I didn’t know I had a problem. 


[07:29] Stephanie Wittels Wachs: This is Calvin McKesson, also known as DeRay and TeRay’s dad. He described himself growing up as an awkward bookworm. He was the kind of kid who would try to memorize the dictionary. Needless to say, he didn’t feel like he belonged. 


[07:45] Calvin Mckesson: For me, it was just peer pressure. Just wanted to fit in. I had no idea what I was signing up for. And that’s the thing about a person with addictive personality, you know, none of us say, “I want to grow up to be a drug addict. You know?” It was an escape from being lonely. You know, I was always somewhat of an introvert and I never fit in no matter how hard I tried, you know, like I said, I wasn’t popular. I couldn’t sing, dance, play sports or anything. So drugs was my escape from reality. My first hit, just like anybody else, was total euphoria. And I thought it was the best thing ever happened to me. But once again, it allowed me to escape the isolation and loneliness that I’ve always felt in my life. 


[08:36] Stephanie Wittels Wachs: Fast forward a few years. Calvin fell in love with a woman named Joan. They got married, started a life together. They were both using, but for the most part, things looked pretty normal. 


[08:49] Calvin Mckesson: You know, me and my wife, we was working, we was bringing income in, and over the years it just progressively got worse. 


[08:58] Stephanie Wittels Wachs: And it was during this period that DeRay and TeRay came into the picture. 


[09:03] Calvin Mckesson: We was happy for both our kids. You know, when she was pregnant, she never used anything. She was clean through both pregnancies. And then when the children was delivered, then it was time to celebrate. That’s just how I was back then. Like I say, we didn’t know we had a problem. For me, it started getting out of control with the loss of jobs. Once I start losing my jobs, I had no way to maintain my addiction. And finally, I hit bottom. I had two kids that I couldn’t take care of, I was five months behind in my mortgage, I’m getting ready to lose my house. It got pretty ugly, pretty fast.


[09:50] Stephanie Wittels Wachs: DeRay and TeRay were too young to remember any of this. Even now, despite being super close with their dad, they don’t know a whole lot of details. 


[10:01] DeRay Mckesson: I think he did a lot of things, you know. We don’t really ask the details and he doesn’t just volunteer them. But he and I talked about it once and he was like, I did a little bit of everything.


[10:12] Stephanie Wittels Wachs: And all of that everything eventually led to this one fateful day with his daughter. 

[10:18] Calvin Mckesson: It’s not something I’m proud of, I don’t know if my daughter knows this story yet. 


[10:23] Stephanie Wittels Wachs: Did he ever talk about his own rock bottom and what that was? 


[10:27] TeRay Ross: I don’t think so. I don’t think we’ve asked. 


[10:31] Calvin Mckesson: If she asked me what made you get clean, I would tell her. But she never asked, so I just never told her. 


[10:37] DeRay Mckesson: He talks about his addiction in very general terms with us. He’s like I used everything. It was bad. It’s like he uses that language with us, whereas like in meetings, he’s more descriptive. 


[10:53] Calvin Mckesson: I have shared it a thousand times in a thousand different meetings over the years. That’s how big of a part she played in my life. I guess you still care about what your children think about you. I’ve just never told her. I’m not ashamed to tell her now, but I just never have. That’s my heart. I just think the world of her. You can’t measure it. 


[11:23] Stephanie Wittels Wachs: TeRay may not know the story of Calvin’s rock-bottom, but she was there for it. 


[11:29] Calvin Mckesson: My bottom was going into McDonald’s with my daughter one day and I bought her a Happy Meal. And I gave her the toy out of the Happy Meal and she didn’t want play with that. And then I gave our French fries, she didn’t want that. I gave her a nugget, she ain’t want that. I was like, girl what you want? You’re not hungry? And she pointed to the soda, she said she wanted the soda. She was about 3, 4 years old, somewhere around there. And she grabbed a soda and took the straw out and put it to her nose and mimicked like she was snorting cocaine. That was my bottom. That was my bottom. When she did that, I realized at that time that little girl’s life was over. And I realized that she was mimicking what she had seen me and her mother do in that time span. 


[12:25] Calvin Mckesson: And it was amazing in that moment. The core of addiction is total self-centredness. So when that happened, my first concern was, did anybody else see this? And I looked to my right. And the course was clear. I looked to my left and this guy, this man, he had seen it. And I saw him shake his head in disgust. And so now it’s time to leave, and I got up to leave, and I go to go to my left and there’s no door. So I had to walk past this gentleman. And when I walk past the gentleman, he stood up. And I was a grown man. I was 28 years old. And I stood there waiting to be chastised by him when he stood up. And he didn’t say anything — as a matter of fact, I don’t think he was thinking about me. He was emptying his chair. But at that time, the shame and guilt had overwhelmed me. So when I walked past him and I walked outside to my car with my daughter, I looked her dead in the face. I told her I was gonna be a better father. And from that day to this, I kept that promise.


[13:31] Stephanie Wittels Wachs: How Calvin kept that promise, and how their mother couldn’t, when we come back. 

[15:59] Stephanie Wittels Wachs: We’re back. While Calvin hasn’t shared any of the nitty-gritty details of his rock bottom with his kids, they definitely grew up very familiar with the broad strokes.


[16:12] TeRay Ross: My dad tells this story, and he tells it all the time — he loves his kids, anybody who knows my dad knows that he loves his kids — but he kind of frames his sobriety around us. You know, I had these two kids, I looked at these kids, and I just knew I had to give them matter. And so I started on this journey, is kind of how he tells the story. And I heard that for a long time as my dad loved me so much that he cleaned up himself for me. But that also sat next to the fact that my mom did not, or could not, or whatever that word is supposed to be. And it made it very, very hard for me to have any kind of like positive feelings around her, because that is the story that was told. Like my dad saw us and wanted to do something different, my mom didn’t. And so what does that mean about how she feels about us, about how much she loves us, about all of that.


[17:07] Stephanie Wittels Wachs: She has more clarity around these impossible questions today, but back then, she really only wanted one thing. 


[17:14] TeRay Ross: I think a lot of it is like I was a little girl and I really wanted a mom. But it was not fun growing up without her. Like, I wanted, you know, someone to teach me how to braid hair, or how to cook, and all those things that I thought little girls were supposed to do. And I had a lot of women in my life, and I think it’s really important to say that, that I had a ton of women that stepped up and really tried to fill that role, but they just weren’t my mom. I remember when I first started my period. I was super young, I was eight years old, and I thought I was dying. And nobody had any of these conversations. I locked myself in a bathroom. I’m not coming out. I am dying. And again, wonderful women had stepped up and did the things that needed to be done, but they just were my mom. And it was definitely something that I struggled with for a very long time. That I still struggle with. 


[18:08] Stephanie Wittels Wachs: Even though it was especially hard on TeRay as a little girl, DeRay had a hard time, too. 


[18:14] DeRay Mckesson: I felt shame about Joan’s absence. I felt like I did something, like I wasn’t worthy of love. And if she could leave, anybody could leave. So I had to deal with that. I definitely felt shame around her absence. And Mother’s Day, stuff like that, you know, everybody talks fondly about their mother, and a lot of people have these father stories, like their father’s not here. We see him all the time, he’s fine. But we don’t see her.


[18:39] Stephanie Wittels Wachs: Their mom not being around felt shameful. But that was compounded by the messages they were getting about drugs from the outside world.


[18:48] TeRay Ross: I think about it from the standpoint that those were the messages that I grew up with. I was in school and it was “just say no.” And when it was, you know, these are criminals and everything, and I just think about how — 

[19:00] DeRay Mckesson: this is your brain on drugs. 


[19:01] TeRay Ross: Yes, with the commercial and everything. And those were the messages that I grew up with, and so that is how I felt about people in my life that were having this experience. And it just makes me sad that I didn’t have the grace to extend when they needed it, because that was the messaging that I grew up with. 


[19:21] DeRay Mckesson: I, too, am reminded of how easy it was to scale those messages. That “this is your brain on drugs” wasn’t some random ad that we had to go search out. It was like that was — it was everywhere. DARE was everywhere. Like the messages that demonized black people who were in recovery and addicted were everywhere. I think if anything, that is like a reminder of how easy propaganda is, how demonizing people color is just politically powerful and easy to do it. And like TeRay said, I think about the fallout, like what happened to families because that grace just was absent. That people made jokes about families and like, again, that’s something that I know much better as an adult, is that like Lord knows, everybody’s family, especially in Baltimore, is dealing with addiction in some way. So like those jokes, touched people in ways that you may not see, but like it has an impact on people’s family. And I’m much more sensitive to that today. 


[20:21] TeRay Ross: I mean, so there was shame in the sense that I knew that you were talking about my fill-in-the-blank, and I was aware of that. And I really, looking back, I just felt like they were bad people making bad choices that happened to be related to me. 


[20:40] Stephanie Wittels Wachs: And from a very early age, the bad choices were very visible to TeRay.


[20:46] TeRay Ross: I don’t remember a time in my life that I was around her where she was not drinking, and all of the big negative memories come around her being drunk, like stumbling, “I’m not sure who you are” drunk.


[21:02] Stephanie Wittels Wachs: Seeing her mom so drunk that she didn’t recognize her own daughter was really hard on TeRay. DeRay didn’t really get it on this level, but the whole experience has left him with a blank space, a void where his mom should be. 


[21:19] DeRay Mckesson: And again, the difference between TeRay and I, TeRay remembers Joan. TeRay remembers Joan the person. Whereas I was so young that I remember Joan the idea more than I remember her the person. And because our house burned down when we were in elementary school, we don’t really have anything sort of from that era that would be like, oh, this is like the toy that she had for me. I don’t know. Like none of that stuff exists. 


[21:43] Stephanie Wittels Wachs: OK, so when they were in elementary school, DeRay and TeRay’s house burned down, like, to the ground. One day they lived there and the next day they didn’t. And in addition to all the addiction stuff, this was yet another trauma that these kids had to deal with. And now TeRay is the principal of an elementary school, where every day she sees kids who are struggling with the same things she did. And this is the point in the conversation when DeRay, being the expert interviewer that he is, jumped in to start connecting the dots. 


[22:21] DeRay Mckesson: I wanted to ask TeRay — because I’ve never asked you this — is how has being a principal and interacting with so many parents who are going through their own journeys with their kids, especially because you’re a principal at an elementary school. Like, how does that inform the way you think about parents who struggle? 


[22:44] TeRay Ross: Oh, I just get it. I get it in a whole different way. Like I get it for the kids, too. I mean, if we if you think about how it happened, so we grew up without our mom. We knew she had a drug issue, alcohol issue, whatever the issue was. The house burned down, we were displaced, we were homeless. We were doubled up in — like, these are issues that my kids are dealing with every day. And so when they come in and they’re like, you know, I slept on the floor with my three cousins last night, I understand that in a visceral way. I get what that means, I understand that you didn’t sleep as well as you planned on sleeping. And now you don’t want to hear nothing about ABC, 123 because you’re tired. And so I think it just gives me a level of empathy and compassion that our families need. 


[23:32] DeRay Mckesson: I never thought about the fact that we were homeless. We were homeless. That house legit burned down.


[23:37] TeRay Ross: I thought about it recently because we were dealing with a transient family in the school. But like no, we were homeless. Our people at that school didn’t see us again. We just didn’t return. 


[23:52] DeRay Mckesson: I just never literally — and I’m going to add that all I do is activism, and I never even considered we were homeless. You’re right. One day we didn’t go back to school. We went to a whole different school that year. Yeah. We slept in my grandmother’s — we slept in the living room. My grandmother had like a — 


[24:13] TeRay Ross: Y’all slept — I slept upstairs with Leeka. I was in a room with my aunt. And we just kept going. We kept moving. 


[24:25] DeRay Mckesson: And it’s crazy to go back to grandma’s house now. You’re like whew, this is small.  But it felt so big as kids. We did that whole year there and it never — I don’t have no scarred memories from that year. I mean, I always processed that we lived in a living room, but I never considered that we were homeless. You’re right. That makes sense that you’re dealing with the transit family made you. Look at me TeRay, having breakthroughs on a podcast.


[24:56] Stephanie Wittels Wachs: DeRay remembered the house burning down. He remembered losing all of their things. But he didn’t think of this experience as being homeless because he felt so at home at his grandma’s house.

[25:08] DeRay Mckesson: So at my grandma’s house it was interesting because it wasn’t just my grandmother, but it was like my aunts and uncles and cousins. So a lot of people watched us over there. So that’s why I don’t remember the transition being rough is that I always wanted to go over to grandma’s house because I could see my cousins. And our aunts and uncles were so important to us as kids. Thank God for them because they were all so different. And it is interesting to be an adult to just see how addiction has impacted our whole family. So not only our parents, but almost all of our aunts and uncles, and what that means in terms of — addiction just has had such an impact on the way our family unit is structured outside of sort of me, TeRay and Calvin, and TeRay’s family at this point.


[25:54] Stephanie Wittels Wachs: Growing up, so many of the adults in their lives were using. And it felt like all of them, including their mother, were on the same team. 


[26:04] DeRay Mckesson: They never say anything negative about her. When we would say negative things, they’d be like, oh, no, that’s your mother. I’m like, where is she? They’re like, oh, she– I don’t you know, it was never negative. That’s what I do remember. It was like never negative about her. Our father was never negative about her. And my grandmother and great-grandmother would always be like that’s your mother whenever she came up, the idea of her came up. 


[26:30] TeRay Ross: And they were like, wildly supportive of her in a way that I remember being really frustrated about as I got older. To the point where my grandmother’s house, my dad’s mom’s house, was always open to my mom. If my mom had nowhere to go, she was going to end up at my grandparents’ house. And I remember, you know, in high school, just stopping past my grandmother’s house, and my mother was there. And it was always this awkward like, what is she doing? You know, like, why? And I think now I can really appreciate that they have always been on her team and always, you know, on her side trying to get her together or help her get herself together. But I remember moments of like, why are y’all doing all of this for her? 


[27:15] Stephanie Wittels Wachs: And a lot of that was directed at Calvin, who to this day still talks about her with the utmost compassion and empathy.


[27:26] Calvin Mckesson: People need to understand you have to separate the disease from the person. Their mother was a wonderful person. She never caused any harm to anybody but herself. But it wasn’t her that I was upset with, it was her disease. And, you know, God being who God is, you know, you got to allow that her process for what she needed to go through to hit her bottom. So I never bad mouth the kids because I understood there was a disease that had her in the grips. It wasn’t her. She was a beautiful person. She still is today. 


[28:05] Stephanie Wittels Wachs: You know in movies where a person jumps in the water to try to save someone who’s drowning, but the person who’s drowning starts to weigh the rescuer down and then they both start to drown? This was Calvin and Joan in those early days of his recovery. 


[28:21] Calvin Mckesson: My process of recovery was prolonged because I kept trying to save her. In other words, I would get clean, then I would go back in and try to save her. And I would end up using again. And I did that several times until she finally went into treatment. When she went in treatment, she met somebody, and she left me for a gentleman in treatment. And then, you know, as I came out of denial and I realized that I had to get out of God’s way. I couldn’t save her, but God could. And then that’s what my recovery started. 


[28:57] Stephanie Wittels Wachs: Calvin started the process of recovery, but he wasn’t ready to stop fighting for Joan, because he still felt like their fates were tied up in each other. 


[29:07] Calvin Mckesson: My sponsor, he asked me, Calvin, why you kept trying to save her. And I said I kept trying to save because I believed that if I divorced her, that she would get custody of the kids. Cause back then the woman always got custody of the kids. And he said, that’s not true. He said, you see that guy — we was in a meeting — and he said, you see that guy? I said, yeah. He say he got custody of his kids, why don’t you go ask him how he did it. So I walked over to him, I asked him how you get custody of your kids. He reached in his wallet and gave me the card to his lawyer. 


[29:39] Stephanie Wittels Wachs: Calvin reached out to that lawyer, got really specific, actionable advice that he followed.


[29:45] Calvin Mckesson: And from that day to this, I had custody of my kids. So when I got into the fellowship, the fellowship through empathy, I found out that there’s nothing new under the sun. So what I’ve experienced, somebody else had already been there. And that’s the foundation of recovery. It’s empathy. People understand not through sympathy, but they understand through shared experience. 


[30:09] Stephanie Wittels Wachs: This shared experience was a huge part of his recovery, but so were the 12 steps. And I have never heard a better CliffsNotes version of the 12 steps than Calvin’s.


[30:20] Calvin Mckesson: I’m gonna break it down like this real quick. They say step 1, 2 and 3 is giving up; 4, 5 and 6 is cleaning up; 7, 8 and 9 is making up; and 10, 11, 12 is keeping up. And it was through that process that I actually matured into the man that I am.


[30:39] Stephanie Wittels Wachs: Calvin feels like he grew up in 12-step recovery and so did his kids, literally. 


[30:45] DeRay Mckesson: So we grew up like going to meetings — and by “going to meetings” I mean sitting in the back of meetings and like being babysat by somebody, stuff like that. 


[30:55] Stephanie Wittels Wachs: Growing up around this spirit of generosity, and being in the rooms at such a young age, had a pretty significant impact on DeRay and TeRay. 


[31:05] TeRay Ross: Like I was saying the Serenity Prayer at 15. When I felt like life was too hard, I needed the Serenity Prayer. I understood the concept of like, keep coming back, keep coming back. Don’t give up. It works when you live it. So like, yeah, I think we just — or I’ll speak for myself — I just grew up with these mantras of like find a higher power, you can only control certain things that are within your control, don’t give up. And I definitely think that those are messages that I got through my dad going through his process that have stuck with me forever. 


[31:40] DeRay Mckesson: Yeah. It’s funny TeRay, I forgot all — you know when you take things for granted. I completely forgot that “keep coming back” in an N.A. phrase. 


[31:50] TeRay Ross: It works when you live it every day. Actually, now that you say that, I have a chip. Like I’m grabbing my keys, I have an N.A. chip on my keys right now that says “just for today.” And like I can’t tell you how many times I’ve grabbed this chip. I’m not in N.A. at all, but like the chip was really important to me. And it’s on my keychain. 


[32:15] DeRay Mckesson: And like I remember going to daddy’s anniversaries. Or going to the beginning of them and then leaving when he was giving a talk. Yeah. So a big impact on me, too. I think that for me, in addition to what TeRay said, you know, I just echo all those things. N.A. was my first sort of community outside of family that I like understood what a community felt like, like everybody chose to be here, people love each other, like the sense of a place to go when you struggle or need help, and like sharing your story, all that stuff. Like the idea of, the power of sharing your story and being really vulnerable and really honest and there’s a community of people to help and support you and this idea that you actually keep doing that. You don’t just come one day. You, like, keep coming back. That stuck with me and shapes the way that I think about what it means to build community and the importance of being vulnerable. And why we tell our story, those sort of things that are important to me. 


[33:10] Stephanie Wittels Wachs: Also, Calvin always had a speech in his back pocket. 


[33:14] DeRay Mckesson: But Lord, as a kid, it was like you ask one simple piece of advice or whatever, it is like, OK, here we go, daddy. So there’ll be moments where you’re like, can I get like the non — not N.A. version? But can I just get a little something, not a sermon?


[33:30] TeRay Ross: He’d be like, “that’s actually step 6, DeRay.” I’ll definitely piggyback on the vulnerability piece, though, and especially with men. I think my dad’s involvement in N.A. showed me men who were saying, “I need help.” And I mean, if you ever get to talk to my dad, he’s a complete open book. He’s gonna cry if he’s sad, he’s gonna laugh if he’s happy. So he is vulnerability in and of himself. But just to see so many men through the house saying, hey, I need you, or, hey, you know, this is going on, I can’t talk, but I’m just going to come, definitely kind of just shaped some ideas about masculinity and what it can be versus kind of what is projected to be out in the world and what some of my other experiences are. So that has been interesting, too.


[34:22] DeRay Mckesson: That makes sense to me. I like that.


[34:25] TeRay Ross: I’m smart.


[34:29] Stephanie Wittels Wachs: The other thing they understood about Calvin’s recovery is that you’re never done. It’s a process. Always and forever. And that’s OK.


[34:39] DeRay Mckesson: I remember really having to process — I get it now, but having to process this idea that you’re always in recovery. Because it’s like, daddy, you have been to more meetings than anything I’ve ever done in my life. He’s like, “y’all wanna come”? For what? We’ve been to them since we were kids. And like the idea of like that not being weakness, you know, like being strong enough to know that this support is what got you through, and then part of your commitment is to like pay it forward and you still need it has been really informative to me. 


[35:13] Stephanie Wittels Wachs: It’s interesting. As adults, both DeRay and TeRay, avoid substances of any kind. It is extremely rare that they’ll even have a drink. But even though they don’t have any firsthand experience of addiction, their proximity to a recovery community has shaped DeRay and TeRay into two of the most empathetic people you will ever meet. And since becoming a mother herself, TeRay’s empathy for her own mother has grown even deeper.


[35:47] TeRay Ross: And as a mom now, I 100 percent believe that my mom missed us every day. I don’t believe she just walked away from us. I don’t believe she just chose something else. I just don’t believe mothers in general just choose something else. So I 100 percent believe that she couldn’t, she couldn’t. She couldn’t make the choice to be there for us. She couldn’t give us what it was that we needed. And sometimes I believe she made the harder choice of, you know, going this way and being on the outskirts and not really being able to be involved as much as I believe that in her heart she wanted to be involved. I think it’s also, as a mom now, makes me think a lot about what I expose my kids to. And when I think especially about addiction, because my mom is one of many people in my life that are struggling with addiction. And when these people are clean, they are the best people I know. They have the biggest hearts. They give the best hugs. They love on you genuinely. And I’m always playing this game of like, how much do I let my children fall in love with how wonderful these people are, knowing that they have the potential to get caught up in this thing again and not be these wonderful people that I’m now exposed my children to. And that’s a hard one, it’s really hard for me to sit with. I have an uncle that my kids really, really love and when he is clean, he is the best person in the world. He is literally the best person I know. And when he’s not, he’s just not. And do I want my kids to love that person enough to also be hurt by that person to the same degree, is a game that I play every day. Like I had this really great really show with my grandmother that my kids won’t have with their grandmother. So it’s like this ongoing place of empathy, compassion and trying to hold space for my own feelings at the same time. 


[37:54] Stephanie Wittels Wachs: TeRay’s understanding of her mom’s sickness has changed so much since she was that little 4-year-old girl. She still doesn’t have any power to change her mom’s behavior, but she can decide how that behavior impacts her and her kids. Today, she and DeRay have different relationships with Joan. DeRay doesn’t really talk to his mother, but TeRay feels a sense of responsibility to stay in the loop. And it’s hard because Joan is getting older and she’s dealing with even more health complications. 


[38:30] DeRay Mckesson: Joan had a stroke. When did she have her stroke, TeRay? 


[38:34] TeRay Ross: Two years ago? Two, three years ago. 


[38:38] DeRay Mckesson: And I haven’t seen her — you’ve seen her since haven’t you? 


[38:41] TeRay Ross: In the hospital, yeah. 


[38:43] DeRay Mckesson: Oh, she’s — daddy made it seem like she wasn’t, like, recovering well? 


[38:47] TeRay Ross: She’s not. She landed at my father’s mother’s house, and that is where she has been. But she’s not walking well. She’s not speaking well, like she’s not healing. But I also know she’s still drinking and I know she’s still doing other things that aren’t going to allow her to heal. So it is kind of an acceptance that this is who she is at this point, and I’m not sure that anything is going to change. And, you know, I’m always waiting for another phone call. 


[39:21] Stephanie Wittels Wachs: Waiting for the next phone call pretty much sums up what it feels like to be tethered to someone who’s in active addiction. When she was a kid, she waited for her mom to get better. Today, she’s waiting to hear that things have gotten worse. Hearing the whole story, it makes sense that TeRay has been saying the Serenity Prayer since she was 15 years old, and that her dad continues to say it today.


[39:50] Calvin Mckesson: I believe on an individual basis, the key to happiness is acceptance. Anything you can accept, you can conquer. If you can accept it, it don’t have to conquer you. And true acceptance is found in the Serenity Prayer. And I just want to share this prayer. God, give me the serenity to accept things I cannot change, the courage to change the things I can and the wisdom to know the difference. Living one day at a time, enjoying each moment at a time, accepting hardships as a pathway to peace. And for me, that’s what life is about. Just accept things as they are. 


[40:29] Stephanie Wittels Wachs: Thirty years in recovery has given Calvin a lot of things. Knowing what life is about. A strong relationship with God. An endless stream of selflessness and compassion and empathy. A deep understanding of the things that he cannot change. And the greatest gift of all: More time with his kids.


[40:50] Calvin Mckesson: My kids are the two best kids any parent could ever have. They never gave me a day’s worry. So it was easy for me because they was good kids. And I had the support of my family. But you know, when DeRay — we always say we had this moment that love is the why. That was our wow moment was that love is why. Love should be why we do what we do. 


[41:20] Stephanie Wittels Wachs: Calvin’s kids were and are his why, and they totally adore him. But at the end of the day, the love they have for each other is unmatched.


[41:33] TeRay Ross: When I think about family, I think about my brother first. And then I think about my dad. And then everybody else. I always feel like it’s TeRay and DeRay against everybody else. And not necessarily against everybody else, but we’re going to be able to figure it out. I’m always gonna have his back. He’s always gonna have my back. And we got this because it’s us is, it’s always going to be me and my brother. 


[42:00] Stephanie Wittels Wachs: DeRay and TeRay against the world got them through childhood. But as adults, they both spend their days shaping the world. And as it goes with siblings, their relationship continues to evolve. 


[42:18] DeRay Mckesson: You know, we became super close when TeRay became a mom. You know, I remember driving to the hospital in the middle of the night when Isaac was born. 


[42:29] TeRay Ross: I mean, you liked me before 2010. 


[42:30] DeRay Mckesson: I know, but we became even closer. Why is she like this? 


[42:33] TeRay Ross: Are we going to talk about how I like planned all your lessons for you. 


[42:41] DeRay Mckesson: Now she’s lying! She’s lying. Yes, I needed advice from my sister. Wow. This is a really revisionist history.


[42:54] TeRay Ross: We love each other. 


[42:59] DeRay Mckesson: She’s great.


[43:01] Stephanie Wittels Wachs: I mean, is there anything as good as sibling laughter? Of all of the things that I miss about my brother, that special variety of laughter is at the top of the list. And now that we have reached the end of this supremely beautiful episode, I got to tell you that this week, this whole month really, has been really hard for me. Especially while working with this amazing tape of a brother and a sister who are so there for each other, because today, February 19th, 2020 is the five-year anniversary of my brother’s death. Which is just crazy. I mean, it is fucking crazy. 


[43:54] Stephanie Wittels Wachs: And for various reasons, this big milestone inspired me to torture myself this week by sifting through all of these old home videos, and I found this little gem from Harris’ 15th birthday. We’re all sitting at this long banquet table full of way too many 15-year-old boys at this Mexican restaurant. And I’m leaving for college in a few months, so I’m giving this very over-the-top dramatic speech to the camera about how much Harris will miss me when I’m gone. 


[44:31] Stephanie Wittels Wachs: You think you’re not gonna miss me, but you’re going to miss me. I have to say, I’m the best sister you could ever ask for. And even though it’s hard for you to admit how much you love me, I know you do. And I love you. And happy birthday. 


[44:50] Stephanie Wittels Wachs: And instead of mocking me like he typically would, he said this.


[44:57] Harris Wittels: I love Stephanie. I love my sister.


[45:04] Stephanie Wittels Wachs: Oh, it kills me. I look at these home videos and I think neither of us had any idea of what was coming. I felt so secure in the fact that we were always going to be together that I actually felt the need to convince him that he would miss me when I was gone. And now, 20 years later, on the anniversary of his death, here I am desperately missing him. I cannot control how shitty this feels. I cannot control what happened to him. The only thing I can do is just surrender to these feelings and accept the fact that for a brief moment, I had a brother. And I loved laughing with him and I miss him very much.


[46:18] Stephanie Wittels Wachs: Next week, we played the blame game.


[46:21] David Smith: I think there’s one piece of this that we are looking for the culprit. We’re looking for the guilty party that we want to hold accountable. That’s a very human thing, very American thing. I do think, though, the other thing we’re trying to do is we need some reparations. There was a significant amount of money that flowed to a business on the back of spurious claims and ignored evidence. And we’ve seen whole communities devastated as a result of that. 


[46:58] Stephanie Wittels Wachs: Last Day is a production of Lemonada Media. Our producer is Jackie Danziger. Nicolle Galteland is our associate producer. And our assistant producer is Claire Jones. Kegan Zema is our technical director. Bryan Castillo is our editor. And our executive producer is Jessica Cordova Kramer. Our music is by Hannis Brown. Special thanks to Westwood One, our ad sales and distribution partner. You can and should find us online @LemonadaMedia. And you can find me online @wittelstephanie. If you like what you heard today, tell your family and friends to listen and subscribe, rate and review us on Apple, Spotify, Stitcher or wherever you get your podcasts. It really, really does help make an impact. I’m Stephanie Wittels Wachs. See you next week.


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