Chicago Spotlight: A Conversation With Steve "Miggedy" Maestro

Born & raised in Chicago through two Belizean parents, Steve’s musical journey started at birth through osmosis. His journey marks are with vinyl, instruments and action. His humble musical beginnings included guitar & piano lessons & choirs until the Hot Mix 5 and Prince came into his life. Striving to do both produce & DJ, he started his professional DJ career spinning in Army base clubs on and off post while serving. He also played guitar, bass, keys & drums in many bands during his military career until he came back to Chicago. Steve landed a mix show jock position in the fall of 1993 on Chicago’s #1 station, WGCI. By mixing smooth blends of House, Old School, Hip Hop, R&B & Reggae, Steve quickly became a household name. Since then he has gone on to mixing for syndicated powerhouse Super Radio, Tom Joyner & Doug Banks, doing production & remixes for Steve ‘Silk’ Hurley, Joe Smooth, DJ Kool, Janet Jackson, Erick Sermon, Tyrese, George Clinton and Faith Evans.  He started his record label, MMP Records, through another Chicago DJ Raphael, by selling his instrumental downtempo R&B tracks on CD for local dancers. Since then he has produced U.K. soul siren Julie Dexter’s full-length album, “New Again” on Ketch-A-Vibe Records, released the “Bop Padow” EP on Unified Records, “Happy Place” EP on House4Life Records and the Julie Dexter “Make You Dance” EP with Vick Lavender’s Sophisticado Records. It wasn’t until he released “Tribe Deep” on Void Digital Music when he met & partnered with Jerry C. King; CEO of Kingdom Music Digital Group.  I recently had a chance to talk to Steve about his career as a DJ, Producer, Remixer, Radio personality and Label Owner.  We had a chance to talk about his longevity, his thoughts on the music and the Chicago House Scene.



Black Widow:    You grew up with music in the center of your life in a home where house music was always played, how did your childhood/teen years influence your love of music?

Steve Maestro:  My thing was always music.   If there was a choice between toys, clothes, or records…the choice was always music.  My dad was the DJ/Music enthusiast in the family. He had all the records and as a child I used to scratch his records, I was doing that at a very young age. I was scratching up my daddy’s records, so you know I was getting my butt whopped! {Laughter}

Black Widow:  You can’t scratch ya daddy’s records!!! [Laughter] So as early as you can remember it was always, music, music, music.?

Steve Maestro: Yeah man….I was getting my butt whopped and didn’t give a damn. [LAUGHTER]  When my parents had their parties, I could put my daddy’s records back in their respective jackets and I didn’t even know how to read. That was at 3 years old!  This wasn’t a hobby, it was my life.  It was my destiny. Innately I think I’m a born entertainer. I would imitate this artist, The Mighty Sparrow.  He was the Michael Jackson of Caribbean music. I would sit on the hammock and imitate him. His voice was dynamic and what he sang about was so diverse.  It was sex, politics, relationships and it was in my native language. I carried all that inside of me; the rhythms and such.  My parents had such a diverse love of music. My dad liked Joe Crocker, Janis Joplin and my mom liked Dinah Washington, Bessie…all these dynamic people.  You know you listened to what your parents listened to.

My parents put me in music lessons. I started guitar at 7, piano at 11, then I went to high school and Prince came into my life. 

Black Widow:   You went to Whitney Young right?

Steve Maestro:   Yeah…Yeah…   It was right around, Prince’s album, “Uptown” I wasn’t just into the records; it was the artwork and the credits.    I was fascinated with the credits. What was a producer? What was an executive producer? What was the difference between the two? When I saw that album and read that Prince did it all (write, perform, and produce) I was stunned.  I started to learn how to play bass and then I also had a band called "Intimicii"; we were basically a Prince Cover band.  I was learning music and DJing in high school. I was practicing both. I was obsessed with it and would stay in the house making tapes.  That’s how my cousins got my name out there.   I was always in the house! I was inside learning music and the craft.  My senior year of HS, I told my parents this is what I want to do. I knew it! From there I went to Roosevelt and did two semesters there and went to the army.

Black Widow:   Why the army?

Steve Maestro:  I didn’t see the point of going to school and learning stuff I knew already.  Instead of my parents paying for my education, I could do this, and learn a new skill.  The 2nd thing I did at Fort Campbell was look for a DJ Job.  I’m at a barracks and the club was right across the street. Because I had the music in me, I could break down house, hip hop, go-go, all the cuts. On Friday and Saturday nights it was my job!  I was in the army being DJ GI Jack!  I was in bands, and DJing 3-4 times a week. 

Black Widow:  When did the radio work start coming in?


Steve Maestro:  I came back to Chicago about 91, living at home and used my GI bill, went to Devry, then Columbia college, while working at Coconuts Record Store on Addams/Wabash for 2 years then a DJ told me about a contest where you could DJ along with Mike Dunn on WGCI. I didn’t think I had a chance.  Its super clichés here and I wasn’t really part of one.  I wasn’t going to do it but I’m glad I did because Elroy called me and said, “Hey you are kinda hot. Come down and do ya thing”.

That was the beginning of that chapter

You have to understand…I’m coming in without a crew behind me.  Back then I didn’t know Pharris, I didn’t know Mike, I didn’t know Terry... I didn't know anyone.  I come into the station. At first they didn’t want me to do house music.  I came in doing hip hop and R&B.   That was the first month then they let Mike Dunn go.  You have to understand how that looked on me. At the end of the day, I gotta walk in these streets and it appeared as if I was the reason he was gone to anyone who didn’t know me.  Mike and I had this distance for about 5-6 years because he thought I was behind it.  I was in this position and I have to do what my boss says.  The boss (Elroy) says, play Hip-Hop and R&B for 1st two hours, then house the last two hours but the streets got a hold of me and was like, “run that ole school”.  So that’s what did, and then they let me go…

Black Widow:    OH WOW!  Get outta here!

Steve Maestro:  Yeah…for a whole week people in the city faxed letters to the radio. They had my butt back at work within a week. That’s how I was accepted.   I was serving.  Then Clear Channel came and wanted hip hop. So they were like screw house! You gonna do hip hop or you’re out. We did that for 3 years before they cancelled club 107.5.  I had to do what I had to do.  They made me show director but that’s just another word for supervisor. I had to review 4-5 other DJs mixes and do my own.  Then Power 92 popped up and served the streets and filled that void that Elroy couldn’t at that time. 

Black Widow:  So you got caught up in the corporate bureaucracy.  You are getting into the corporate red tape. That will kill your creativity.

Steve maestro: Yea and it kinda sucked the life out of me. I’m a producer/DJ/artist.  I wanted to be like the Steve Hurleys, the Frankie Knuckles’…that was the plan.  I was doing syndicated mixes for super radio doing R&B/Hip-Hop on one side and old school on another side. That was one hustle. Then Steve Hurley hired me to do work with him. I was doing records with him and from there started doing mixes for Tom Joyner. Then Doug Banks went syndicated and the first person he tapped to do mixes was me. So I was doing mixes for Doug Banks, Tom Joyner, Super Radio and WGCI.  I was tired and still trying to get production done and DJing. DJ’ing was something I enjoyed but the producing was more serious for me because I equated it with more money.  I knew producers were the ones who got paid and that’s what I wanted to do.  But they kept me on the DJ thing forever and it got the point where I had to leave.

Elroy and I had a unique relationship. Back then I encouraged him to make radio sound like Chicago. Play our music…we taught each other a lot and were great friends. He even started to like house.  He started to pay attention to the culture and you felt that during that time on the radio. He said play what they know then do your thing. 

Black Widow:  You talk about the transitions in radio.  As a DJ on the radio, how did you balance what you wanted to do with what the station wanted?


Steve Maestro:  You know back then I was 24-26, I did house and old school that was my lane. They let me do my stuff on Fridays and I did the lunch mixes and stuff during the week. That was my balance. Then Clear Channel came in and said screw that.  At that moment, the 90s hip-hop was poppin, it was great for me! I could do all of that.  But then some of the southern hip hop got popular and then I started to lose for it because I couldn’t relate to it.  It’s no diss, it just wasn’t my vibration.  I was enjoying that but I wasn’t enjoying the environment that came with it.  It was a lot of that coming up in the clubs too.

Black Widow: That’s when I was introduced to you. On the radio, when I was in high school. My connection to music was via the radio since I couldn’t go to the parties and such.

Steve Maestro:  What I discovered is that I didn’t come in via the circle. Those clichés were inbred because of how everyone grew up. That was when black people really ran the Southside.  We are grandkids and great grandkids of that. I grew up north, my experience was different but when I started talking to Pharris, Wayne, Mike, Terry, and when we started to understand each other it was all good. You know initially, no one understood me, I didn’t fit in.  I wasn’t from where they were from.  It wasn’t until I left WGCI and went to NYC, and came back to Chicago to 106.3 that Mike and I talked and I explained to him what happened and we cleared the air. It was so many other people who were feeding into that madness, people who didn’t like me, talking to him and vice versa…it was crazy.

Black Widow: That’s something isn’t it?  When two people have a conversation? 

Steve Maestro: I know! Exactly! There was always this thing between DJs, this divisive thing with Radio DJs vs Street DJs. I never understood that because I was just as much a street DJ as I was a radio DJ. I mean how do you think I got on this? [Laughter]

Black Widow: So now you are DJing and working on the radio, where did producing come into play?

Steve Maestro:  I was always doing production.  I was trying to find my lane and discovered it was R&B, steppers, and house.  In 2009, I met Julie Dexter and we did an album together, then I met Jerry King, my business partner and that becomes the third leg of my journey.  The artist/producer/label with him and the DJ thing in the streets. My goal has always been to be as diverse as possible.  All races, colors…its money in all of that.  I’m concentrating on the music; he’s concentrating on the business. We are both musicians and we speak the same language and it’ works. He’s my Jimmy Jam. It’s a true partnership. He’s my business partner.  We strengthen each other with our different parts.

Black Widow:   How were you introduced to House Music?

Steve Maestro:   It was a natural progression. For me it wasn’t about a classification of music because of how I was introduced to it. I didn’t know what it was.  To me, it was just my daddy’s music.  I was always inquisitive; I would listen to Ralphie Rosario at noon and would listen to him every day. I wanted to know what this was. I started taping mixes and taking them to Loop Records.  I would ask Jesse Jones what is this?  I already understood the art of looking for records because my dad would take me record shopping. My dad was so cold with it; he could look at the album cover and know it was a dope album!   And Whitney young was a huge part of that too!  Whitney Young was on the Westside but it was Southside all day long!

Black Widow:     You are very open on social media in telling your story about your career and what you have seen and sharing your history.   Why do you think documenting and telling our stories is so important, particularly with this genre?

Steve Maestro:   Cause a lot of us don’t. I see what was done with rock, blues, and jazz.  We created it, they labeled it.  House included. I think now, I’m old enough to articulate it and give it to you in laymen’s terms so the young people can understand it. Don’t get it twisted; some young people don’t believe what’s out there is the only thing poppin. With the internet, all it takes is one kid who’s into something different to get a hold of what we are doing and spread the word amongst younger generations.

Black Widow:  I’m glad you said that.  You mentioned putting it out there in laymen’s terms.  In my experience, sometimes people have talked down to me in a way when talking about the history and I don’t think it’s done on purpose but it’s definitely a tone to it.  Because I’m younger, because I wasn’t around during the 80s, etc. in their desire to tell me what it was like, they talk down to me.

Steve Maestro:  People and their egos….I went through that for months in radio.    I’ve learned that some people don’t like change and they don’t like accepting new people on someone else’s terms.   People don’t understand you are exposed to what you are exposed to when you are exposed to it. You can’t penalize folks for not being born at a certain time! [LAUGHTER]

Black Widow:  [LAUGHTER} I KNOW!

Steve Maestro:  It’s also checking for the phonies.   It’s like a hazing; trying to make sure you are real. You know we’ve caught some who front like they were in certain spots when they weren’t but you can be protective of the culture without being abrasive about it.

Black Widow:  That’s the challenge we face now as the storytellers to younger generations…not to be so abrasive and to be more inclusive.   This is why I bring my kids to certain kid friendly house events. I want them to see this…feel this culture. I want them to see people dancing, feel the energy, and not just standing on the wall hoping a fight doesn’t break out.  I want my kids to feel the difference in the vibes.

Steve Maestro: Exactly!  Yes it’s such a difference and they need to see that!

Black Widow:   I read in another interview that you were a fan of the dancers.  What makes them so important to the DJ and the party in your opinion?

Steve Maestro:  There’s no party without them. You can have everything but if you don’t have dancers, you have no party. Everyone is important to the pie. People don’t get it, it’s not just the DJ, promoter bartender; it’s the people who come to the club.  The dancers attract me more than anything. That ignites me more than anything. It’s not just trust in the DJs, it’s the dancers.  I’ve seen people in wheelchairs do the spin move on a dance floor…you know?  

I grew up in a family of dancers and my dad was DJ for our family unit.  We would pile up in this small apartment with 30 adults and 20 kids and we had a ball dancing to my dad’s music and he had one turntable! It was people partying, drinking and talking shit.   I had the party spirit in my blood already.  At five years old, I would take over and put those records on while my dad was talking and I remember once my grandmother came over and put $5 in my pocket and said; now you’re a businessman. I don’t know why that sticks out in my head but it does. It stuck with me my entire life.

Black Widow:  I love that!!! Those experiences and memories ….I have similar stories too. My grandmother would have parties at her house after she retired and she’d have all the dancers, jazz artists, and singers, musicians from back in the day at her house, partying, drinking and playing cards. I remember I was home from college at the time and I would be there making them drinks! My mom would joke that I went to school and became a bartender and a card shark! [Laughter]   I would listen to the stories they told about their scene, the jazz scene.  We learned how to party from them.

Steve Maestro:  Yes! That was it…that was my dad. 

Black Widow:  It’s why I enjoyed those jam sessions at Alicia’s we would have, where my kids were there and they would see us relaxed and having a good time.

Steve Maestro:  Yes I love moments like those.  Kids love seeing grownups having fun! I know I did when I was a kid.  I took all of those experiences in and I think because we are artists, we get to enjoy people enjoying themselves.   That’s what we get to do; that’s the environment we create, people enjoy themselves while we do what we do. 

Black Widow:  What inspires you to create?

Steve Maestro:  Life inspires me because I can’t do anything else. I tried.   Working a job sucks the life out of you as an artist, at least for me.  It’s about being fearless.

Black Widow:  It’s interesting you mention fear because I tell people all the time; fear pushed me right into where I am right now. From being scared to share my work to what I’m doing right now.  It’s crazy what happens when you stop fearing things.

Steve Maestro:  What are you scared of? That has always been my thing. Once I got over being introverted; once I stopped being unafraid of what was getting ready to happen, it showed in the way I played.  My wife too, she really was my bedrock to my creativity these past 8 years.  When you have another artist who gets it, she saw more than my potential, she saw where I was going with this thing.  She understood where this was going.

Black Widow:   It’s nice when you have a partner who gets it!

Steve Maestro:  Yes and she really fueled my creativity.

Black Widow:  Any DJ Pet Peeves?

Steve Maestro:  Ok, when I first heard music mixing on the radio, I remember hearing actual blends.  A lot of cats don’t know how to blend!

Black Widow:  It’s an art, I will stop me mid-dance! It’s a face I give you if I hear a train wreck!  Having friends who are DJs taught me how to hear music differently. Now I’m more particular.  Even now sitting in studios, my ear is being trained differently.

Steve Maestro:  People always tell me “you spoiled me”…you know how many times I’ve heard that.  [LAUGHTER]  The longer you are around it, you start to see those differences and become more particular. People tend to get mad at that or say you are “riding” certain people...

Black Widow: Oh lord…yes! [Laughter]

Steve Maestro:  We get that so much. You have no idea! I remember Elroy saying when they really start hating on you is when they are tired of hearing your name. That’s the Chicago way.  That means you are doing alright! [Laughter] I swear Jerry and I deal with people trying to get at us while talking shit about us.

Black Widow:  Isn’t that crazy!

Steve Maestro:  It is but it made me realize I was doing something good! LOL.  

Black Widow:  What do you think about the Chicago House Scene now?

Steve Maestro:  You know when people talk about the same music being played at certain spots, there’s a creative wavelength that we are all on at times.  We are in tuned with each other. Certain people make the songs, others are party pleasers and they are all important.

Black Widow:  I’ve had this conversation with friends of mine who don’t come out as much. There are some of my friends who don’t get out and when they are, they will go up for songs I’m tired of hearing but I had to realize they don’t get to hear the music the way I do. It’s different for them.

Steve Maestro: Exactly! The experience is different and that doesn’t ‘make it bad or worse. It’s a place for all of it.  If it’s the hottest record, play it.  It’s really how you choose to handle it as a human being! Fuck DJs…people make a big deal about DJs. It’s how you are influenced as a person by what you do to a community.  There are a lot of DJs who spin well but their insides are negative. If you are selfish, that translates. 

Black Widow:   I tell people when I feel a bad vibe or negativity coming from you as a person; it takes my desire to hear you play away.  It doesn’t matter if you are good…but I have no desire to hear you play.

Steve Maestro:  Your name don’t mean shit if you ain't shit.

Black Widow: [LAUGHTER} THAT’S IT!   As a patron, I’m chasing the experience. I’m chasing that good vibe. I’m chasing the music.  When I come out, I want to feel good. I want to laugh; I want to be surrounded by positivity. Life is hard enough; I can’t do that when you are a horrible person.

Steve Maestro:  You have to get that negative energy off you.  My job is to get you to scream and get that out. I want to take you to another place.  That’s my job.

Black Widow I totally agree!  I want to feel lighter, more hopeful and you can’t transform me with negativity. I want an experience that allows me to feel better in my day to day life. 

Steve Maestro:  That’s why people gravitate towards certain DJs. It’s not hate or anything like that. You can’t be mad at someone at their point of entry in the game.  Elroy wouldn’t have hired me if I wasn’t good. It just is what it is. You can’t be mad about that.   I’ve been blessed so much in this, there’s no need for hate or bitterness.  These bitter DJs…I’m like you can’t hold on to that because you isolate people from you.  People don’t want to be around that.

Black Widow:  YES and you are stifling yourself. Even as a new artist, if I had focused on the hate or negativity thrown my way, it would stifle me. I can’t be concerned with that, it’s not about them. I have to keep doing my thing. 


Steve Maestro:  It’s real like that. Once I figured that out… once I started talking to a lot of these cats, and getting that on the job training, we all had an understanding. I was just putting in that work and the respect came, you have to just keep doing you and…

Black Widow:  Keep those blinders on when it comes to the naysayers!

Steve Maestro: That’s it!

Black Widow:  House and Steppers music is different yet uniquely connected. What do you think the differences are?

Steve Maestro:  It’s not really different.  They just dance differently to a different tempo. Both styles are musical.  It’s a community just like house with their own language, style and culture.  We actually are very similar and it’s a Chicago art form.

Black Widow:  One thing I know for sure is that you KNOW music and music history. Why is it important for DJs/Producers to not just listen to the music but actually know the music?

Steve Maestro:  It makes your work flow easier if you know the language to compute.  Everything has a language; computers, language, hustling, pimpin… Southside has a language. If you are going to anything well, you have to know the language.  The Music we play has a language.  Through the music I get to emote my feelings.  I pick the records I pick because it’s where I am at the moment.  You have to be open, vulnerable…

Black Widow:  I’ve learned that over the years, the more open, and vulnerable I am the more it connects. 

Steve Maestro:  Yes, you have to be fearless.

Black Widow:  That seems to be a common theme in my interviews. It doesn’t matter if it’s a DJ, producer, singer, poet; everyone always talks about this need to be open and vulnerable for it to connect.

Steve Maestro:  Yes! Yes! You have to be and it’s so hard for us sometimes to just strip it down, and open up. To be vulnerable, I’ve done it so much I don’t have a fear anymore. I just doing my thing…there’s freedom on the stage. I totally understand why Michael Jackson said the stage was where he felt most free. 

Black Widow: What does being a Chicago artist mean for you?

Steve Maestro:  We are near water and we are in the center of everything musically, the country and globally. We are always in people’s mouths. If you wanted to make it, you went to New York, LA but you also had to come through Chicago.  We have the biggest and most loyal fan base in the world. I’ve been London, NY and love the music and culture but Chicago is the home of house, blues, steppers, juke, jazz so many genre’s….we influence the world.

We are an epicenter.

That’s just us…

Black Widow:  What does the future hold for you?

Steve Maestro:   I’m focused on bringing people together. The bands and DJs.  We got the Navy Pier gig coming up, getting everyone together, enjoying multicultural events, that’s what I’m about right now.  I’m focused on getting our music played and getting it out there.  70% of the music I play is Chicago Music.

Black Widow:   I could do this all night! Thank you so much!

Steve Maestro:  It’s so much! You have no idea… laughter… the stories the highs and lows from NY and back to Chicago…it’s so much. 

Black Widow I know…we need to do a part 2

Steve Maestro:  Definitely!

Black Widow Thank you so much for chatting with me! 

Steve Maestro:  It was my pleasure!

You can find Steve Maestro this Saturday at the World’s largest House Halloween Party and at the following:

On Traxsource:

On Mixcloud:

On FB:

On Instagram:

On Twitter:















Black Widow

D.Sanders, a Chicago native, is a devoted mother, blogger and writer who is passionate about her family, friends, women's rights, living authentically and telling her story.   She is also a spoken word recording artist under the name, Black Widow. She has been writing and blogging for over 15 years providing commentary and expressing thought on life, love and relationships. Her artistry can be heard on two house music singles, “Rough”, and “Gruv Me” released by Grammy Nominated Producer and CEO of T’s Box Records & T’s Crates, Terry Hunter under the production of Mike Dunn and Dee Jay Alicia. . Both singles reached #1 on Traxsource’s Afrohouse and charted top ten overall as well reaching the top ten in their year of release.  She splits her time blogging about the Chicago Dance Music Scene on and on her book’s website,  She is excited about her debut book, The Sum of Many Things, scheduled for release in June 2017.   She wears many hats but refuses to be placed in a box.  She believes that women are "The Sum of Many Things".  Embracing all of her roles as a woman, she firmly believes in breaking free of preconceived notions of womanhood.   She believes it is her mission to define her own life experience, femininity and sexuality and not have it defined by society.  She openly shares her story with hopes that women understand their worth, power and place in this world.