Chicago Santana found himself on the wrong side of the law in the last few years and facing a 30-year sentence. Fortunately, he learned and understood the law and even after being offered an 8-year plea deal, Santana fought for his freedom and came out victorious.

Wrongful entry and searches led to him being vindicated and back making music, something he perhaps took for granted prior to his arrest. He’s back in the studio and recently released a new single, “Fell In LuV,” featuring White Collar Suge. Santana also has his own label, “Always Talkin Money,” where he plans to work with younger artists while pumping out his own music as well.

Realizing time is not always on your side, Santana vows to up the ante and push out more music to satisfy his supporters. Rebuilding his brand and his name is high on the priority list, as well.

The DMV [D.C., Maryland, Virginia] rapper talks to Zenger about how he got his Chicago name, opens up about his trials and tribulations and lessons learned along the way.

Percy Crawford interviewed Chicago Santana for Zenger.

Zenger: You stepped away from music to take care of a very serious legal situation. How did it turn out for you?

Santana: Everything turned out good for the most part. But what I always tell people, you got real life and then you got entertainment. And from the outside looking in, it will always look like it’s just entertainment, but dealing with regular life, family, legal situations and all of that, you gotta make sure home is alright first.

Zenger: What did you learn from the legal situation that you went through?

Santana: Man… that’s a good question. I’m going to honestly tell you, me dealing with legal situations from a juvenile up to now, what I’ve learned is, you gotta be smart. If you’re an intelligent person, you learn a little bit. And I know some people have more challenges than others. It’s a bunch of law shows and court TV shows out there, but I learned as a person how this all works.

If you don’t have the knowledge, you’re going to suffer. I feel like that’s anything in life. That’s why they say knowledge is power. Especially in the law system, if you don’t have any type of knowledge, you can get played with. What I’ve learned is, you have to really pay attention, know what’s going on, and not assume you know everything.

Zenger: I’m definitely not here to interrogate you, and I don’t know how much you can speak on your situation, but can you discuss some of the legal issues and what you were facing, because it was some real time?

Santana: I had a couple of different situations, but the main situation that I had, I allegedly got caught with some firearms and drugs. It was a big distribution and unregistered weapons case. I’m in the D.C. and Maryland area; you have states like Tennessee and Florida where you can open carry. Their gun laws are lenient. Out here, it’s like if you get caught in New York with a gun. They are going to give you a mandatory five years for it. There are no fines or tickets; if you don’t have that special paperwork to carry it, you going to jail.

The only way you can carry a gun out here is if you’re a police officer or security. If you have a business, you have to write a motion. You have to do a lot to legally carry a gun here. But at the same time, you want to protect yourself. Because we are by the nation’s capital, they make it difficult for everybody.

So, some people take their chances, and I was one of them people. But I didn’t directly get caught hands-on with it on me, but long story short, they were trying to give me the maximum for my trafficking case with the firearms, which was like 30 years. That’s what the paper said, which is crazy because it says, if you get charged with a homicide, it starts at 25 years to life. But drugs start at 30 years. So, what I learned was, for a year to a year-and-a-half, my case kept on getting delayed and drug out. They were trying to get me to take a plea to where I would do eight-and-a-half years, and I would be on probation for the rest of whatever my sentence was.

But my thing was, I know they legally didn’t have the right to find what they found. A lot of people would think in their head… this is why I hate internet street thugs. It be all these internet street clowns that ain’t never been through nothing and don’t know nothing, and their first intellect on something on the internet if somebody beat a serious case is, “He must’ve told. He must have cooperated.” But that’s why I say you gotta know the law.

Certain human beings would think, “Damn, they caught me with three guns. They caught me with a half a brick of cocaine and two pounds of weed.” They will have in their mind that, just because the police recovered that from them, they have to get in trouble. People don’t realize, if they didn’t do A, B, and C, so they could catch you with that, then what you got caught with doesn’t even matter. When I went to court, the judge said, “If they would’ve found a dead body, they wouldn’t have even been able to charge you with it because they went about finding it the wrong way.”

They did an illegal arrest on me, an illegal search, they ran up in my house on some he say-she say things. The police looking at me on the internet and running into me, a bunch of new school millennial things that police not supposed to do. At the end of the day if I wasn’t smart enough to fight it, and I just would have signed the piece of paper to take the plea, because I’ll rather do eight years than 20 years…

Some people would sign off and they ship them off to jail even though they had no evidence on them. If you let them know you’re cool with them doing that, they’re not going to say, “We don’t have any evidence on you.” They going to let you sign that paper and you’re going to be in there.

Zenger: To be home and getting back to your passion, the music, what does that mean to you?

Santana: It’s full throttle now. As soon as I was done with all my legal situations, I came home, they deleted my Instagram. The Instagram that I hit you on, that’s my new one. Hopefully, I get my verified account back. I was just sitting on music. I had a name and a following, but I wasn’t taking advantage of it.

When life changes and you see a bunch of people trying to do stuff that you actually got plugs and been in the mix, you start looking at it differently. In my mind, I need to take advantage of the clout and the opportunities that I do have and grow from it and take it to the next level. If I don’t, I’m going to be in more dumb situations.

Zenger: How did the new single, “Fell In LuV,” featuring White Collar Suge, come to fruition?

Santana: White Collar Suge is my man. We came together for “Fell In LuV.” He just came home. He did about six or seven years. Not to put his business out there, but he did that time for a bank robbery. It’s one of them things where, I really know him from the streets. He been my lil man. We done bumped heads, but he cool. He official in my book. I relate to him.

He was around me before I was Chicago. There are a lot of people I might have in my songs or do music with, who don’t necessarily do music. I’m trying to turn my people on and bring my people up. Of course, I’m going to work with the upcoming artists who got talent, but other than that, I’m going to try and build up everybody around me.

Zenger: How does a DMV rapper get the name Chicago Santana?

Santana: It’s crazy that you say that, because if I could start over, Chicago probably wouldn’t be my name. I thought about changing it in the midst, but I built too much on it, and I pop up on Google too much. But the name came from… if you remember the movie “Poetic Justice,” Joe Torry played the character, Chicago, and he always brushed his hair. I used to be the young kid with a fade, and I always had a brush on me, and everybody would call me, Chicago from that movie.

So, when I started rapping, my name is Santana and the Chicago just stuck. I just put it together. Of course, people will look at it like I’m saying I’m from the city of Chicago, but it has no relation. It was just a nickname. I called myself that not knowing how far I would go.

Zenger: You have songs with guys like Young Dolph (rest in peace), Gucci Mane. How were you able to link with some of the biggest names in the game?

Santana: When I deal with music, I know it is entertainment, but it’s a business too. One thing I’ve learned, and I learned from experience and people doing it to me, at the end of the day, if you always be yourself, anybody who is real will acknowledge you for that. I mess with OJ da Juiceman super hard. He one of the realest people in the music industry. Dolph was real too. I spoke to him two weeks prior to them murdering him. Rest in peace to Dolph. Gucci is real too. Rest in peace to Bankroll Fresh too. That was definitely my man.

All these people appreciated me for being me. I was never trying to be extra. Just like the cases I done caught, I speak on life experiences and what I’ve been through. I express myself by what I’ve been through. I’ll talk about it in my music, but I don’t get around people and talk about it. I don’t tell people too much of my business. But if I put it in the music, I can go into detail about my life experiences.

Zenger: I appreciate the time. It’s good to hear that you’re back in the studio and staying out of trouble. Anything else you want to add?

Santana: I’m going to be dropping a lot of new singles. I’m running my own label now, Always Talkin Money [also known as Always Talkin Millions]. I have a few artists that I’m working with. I’m going to come out and push the youth, while upping myself at the same time. So, I have a bunch of singles and videos dropping. I’m just pushing forward and going hard with it. I appreciate you for getting down with me. I don’t know if people tell you that, but it counts to me. It means a lot.

Edited by Judith Isacoff and Matthew B. Hall