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Chanel Winn DeCarlo, 28 years old, Auburn-Gresham
by Bill Healy

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Chanel Winn DeCarlo is 28 years old and lives in Auburn Gresham. Though the Generation Halsted series focuses primarily on young people, Windy City Times included DeCarlo's story because she reflects on her own youth and experiences with the criminal justice system.

DeCarlo came out as transgender at 16. Her family is supportive, and she holds an Associate's Degree from a local college. DeCarlo occasionally engages in sex work; she says she has an online following and quite a few regulars.

WCT interviewed DeCarlo late one night in September. Excerpts are highlighted here; the full audio interview is available on our website. Reporters gave DeCarlo $20 in Walgreens gift cards for her time, a rarity in journalism that was intended as a gesture of solidarity.

Windy City Times: Can you tell us a little about yourself?

Chanel Winn DeCarlo: I didn't always look as good as I do now. I've had quite a bit of surgery done. And I got into a lifestyle where you either have to be born with money or you just end up having to do stuff.

I've had $60,000 worth of plastic surgery done, and I'm still not done. I never would have made it. And plus while I was in school, I was having trouble just buying my books. Because my parents made too much money for me to get help but not enough money to really put me through school. So I got into adult work. It's not something I wanted. It's just…

My parents support me. But, you know, they're always just worried about my safety or the stuff I have to go through.

I started taking my hormones at 16. But then when I was 17 I stopped, and I tried doing that for a year. And it was just so uncomfortable. I don't even know how to explain it. It was like a rash to me. Everything was just so foreign. I just could not relate to living as a male at all. And it was just so inherently me that there was no coming out actually. Everybody who always knew me, the people I grew up with, they were like: We couldn't quite put our finger on it. But we knew something was different about you. Nothing's changed except for the way you look. You know? It's still you!

WCT: Do you ever hang out in Boystown/Lakeview?

Chanel Winn DeCarlo: Every time I go up there, I go to jail. I have over 60 cases. I went to the penitentiary cause of all the cases I caught up there. I used to live up there too. I mean, the police. They used to take me to jail with my groceries. I'm like: I'm going to the grocery store. You know what? Over here [in Auburn Gresham], if you just mind your business, just leave everybody alone, nobody bothers you.

WCT: When did you realize you were different?

Chanel Winn DeCarlo: I think when I was around 14, that's when I figured out I was different from the other girls. They almost sent me to a Catholic high school. And I was definitely dead set against that. Cause I was not going to an all boys school, cause like I didn't want to take gym. It was just weird because they always wanted you to do stuff. And I'm like: That doesn't interest me. They wanted me to do sports and were trying to get me ready for the priesthood. And I was like: I'm not interested in none of that. And I didn't quite understand it either at that time. I just knew. I knew I wasn't quite like the boys and I knew I wasn't quite like the girls. But I identified more with the girls than the boys.

WCT: Were there any movies or music you heard growing up that had someone trans in them?

Chanel Winn DeCarlo: No. The first thing I ever saw was Jenny Jones, Maury Povich or something. When they had some girls on there. It kinda registered a little bit. But then they were always so extreme. I was like: I'm not quite like that.

But then I had a word for it. And so I started doing research at the library.

WCT: What are some of the misconceptions people have about trans women?

Chanel Winn DeCarlo: That we're over-sexualized. That we do this to have sex with men.

They don't like the overtness of it all, the kids around here. Even some of the guys who mess around, they don't like the overtness of it all. If you just go about your business, some people might laugh, but most people pay you no mind.

They see you and don't see you. Especially if they don't want to even be bothered. It's like: I don't even see you. You're not there.

Especially over here a lot of these guys are looking for transsexuals. They always pretend like they don't know. "Oh, my God, you fooled me! Okay, I'm gonna try something new."

You know what? Whenever I have contact with the police, the law or the court. Whatever they say, I don't say nothing. If they stop me, I just get in the car and just shut up. Give them my name and just go. I have nothing to say. Even when you go to court, it's like. You know my ID says female. But the judge, she's like: "Sir this…But you used to be known as…" That does not matter. This is who I am now. So they already have a stinking-ass attitude. And it's just like: Whatever they say. What do I need to do to get you outta my face?

WCT: How does that make you feel?

Chanel Winn DeCarlo: It really pisses me off. I feel like I have no control. Like when [the police] just pulled over here, I was like: Oh God. Here we go.

WCT: What are some of the positive aspects to being trans?

Chanel Winn DeCarlo: As much as I've gone through and as much as I've had to deal with, I still wouldn't change anything about my life. Cause I'm a real compassionate person, and that comes from knowing what I know. Even them with drugs, I don't condone all that stuff. They know how I am. But you know what? I still have my parents. A lot of them girls get thrown out. My family has never turned against me. So maybe I would be on drugs if I didn't have a place to stay, didn't have family. A couple of my friends who died, I was the contact. Their families were like: They've been dead to us for the longest time anyway. They die and go to a pauper's grave. Nobody claims their body. Nobody even cares. It makes you feel so disposable, like you're not even a real person.

WCT: You said you don't want to change anything about who you are.

Chanel Winn DeCarlo: No. Cause I would be a totally different person, and I probably would be one of those people I don't like: Narrow-minded people who don't know anything, who think that you choose to be gay or I choose to be trans. Yeah! Cause I really wanted this!?

So just from an enlightened aspect — that I'm able to see — I don't know why you're doing what you're doing but I can still respect you as a human. There's a reason for everything even if we don't know why we're doing what we're doing.

And even with everything I go through — there are still miracles in my life. I still have my family. I still have my health. I believe that God cares for me. Everything that I go through, I just try to look at this like: "Okay, what am I supposed to be learning?" so I can pass this test and get past this.

WCT: Are you hopeful for the future?

Chanel Winn DeCarlo: I don't think my life will be much different than it is now.

WCT: Do you want it to be?

Chanel Winn DeCarlo: I do, but it's like: I'm almost 30 with no work history. And then - even with my ID changed now, which was done two years ago, it's like: "You just popped up out of nowhere? Who are you?"

I don't know how much better my life could be: If it was I wouldn't even know where to begin or how to start. With the police now, and that record. It's like: They tell you don't do something. But then they don't give you the opportunities to do anything. Then you get stuck in a hole, then you get stuck in a cycle.

I just don't like police. You know: I understand you're doing your job. If you catch me, you catch me. Do your job but don't overdo your damn job. Treat me with some fucking respect.

WCT: Are there some police officers who have treated you with respect?

Chanel Winn DeCarlo: Very few, but yeah.

WCT: Can you describe any positive encounters?

Chanel Winn DeCarlo: When I got robbed or when I got raped that time, one lady officer gave me some information about some counseling and stuff.

I just pretend like stuff doesn't happen. Even my friends who died, it's like: Forget about it. I've always had to do that.

WCT: Does that work or does it come out in crazy ways?

Chanel Winn DeCarlo: It'll come out in crazy ways. That's probably me acting out. Sometimes I'll just get so bored and it gets to the point where I'll trash my house. And it'll be over the littlest thing. But I figure that's probably from some of the stuff I don't deal with.

I guess I just got into the feeling that people don't care. Even my family.

My family does so much for me. I think that my family…I feel like everybody tolerates me. (laughs) We don't even speak about it no more. I guess that's where I learned everything from. My mother just says she has 2 daughters. She's like: That's a girl. Forget it. And she actually took all my boy pictures down. I think that's just their way of coping. Because they knew I wasn't gonna change. Like when I tried to do that year thing [going off hormones], I was getting really suicidal and I had two attempts. And my mother just said I'd a rather have a live daughter than a dead son.

Generation Halsted is an eight-week series that seeks to capture youth voices not typically represented in Windy City Times and other media. The young people portrayed have many housing situations, gender identities and sexual orientations. The series looks primarily, but not exclusively, at Boystown, where an influx of young LGBTQ people has been a source of controversy. Windy City Times will continue to explore the issues raised here beyond this series.


Next week is the eighth and final installment of "Generation Halsted," and Windy City Times wants to include you. If you've read the stories in the paper, watched the videos online or listened on the radio, now is the time to share your thoughts. What have you learned? What would you like to see and hear in future reporting on these topics?

Email with comments, tweet us @windycitytimes1 or find us on Facebook by Friday, Dec. 28, at 5 p.m. to be included in the final part of the series or after Dec. 28, for possible inclusion in future editions.

Windy City Times looks forward to hearing your thoughts.

Look for WindyCityTimes on and or click the "YOUTH" tab at .

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