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How Lupe Fiasco became immortalized as Chicago’s rap sensei

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Lupe Fiasco wept.

How could he not?

Chicago recently honored the Grammy-winning rapper, also known as Wasalu Jaco, by proclaiming Nov. 10 as Lupe Fiasco Day. Lupe’s dad, the late Sensei Gregory Jaco, was also honored with a commemorative day throughout Cook County on Nov. 11.

The first announcement was read at The Salt Shed after Lupe performed songs from his latest album Samurai. He was home for the Chicago leg of the sold-out The Samurai Tour, where 3,600 of his fans and supporters gathered to sing and reminisce. When Deputy Mayor Kenya K. Merritt walked on stage to read the proclamation, fans were stunned. Then? They celebrated. Fiasco, wearing dark sunglasses and a red designer basketball jersey, stood stoically but also shed a tear while hearing his accomplishments read off.

“I mean, it feels… it feels good,” said Fiasco, a private artist who didn’t want to bare his soul after the announcement, but he did share a little of what was going on in his mind in a Zoom interview with The TRiiBE. “Some of it’s personal. So, I like to keep it to myself. You feel me? It feels good to be recognized by your city. It’s a big deal for the fam.”

The second announcement was read in a memorial ceremony held at the Stony Island Arts Bank on November 11. There, the late Jaco, founder of the Tornado School of Martial Arts, was honored for the decades of his philanthropic and martial arts service to Chicago’s citizens. Vice Mayor and Alderman Walter Burnett (27th Ward) read Sensei Gergory Jaco’s proclamation in an intimate room filled with family, friends, the Grandmasters who trained with and under Jaco, and students enrolled in the Tornado School of Martial Arts.

“The family business has always been martial arts schools and army surplus stores,” said Lupe, who himself earned his 7th Dan Black Belt during this Veteran’s Day ceremony.

Lupe Fiasco (center) pictured with his family including his uncle, his sister Ayesha Jaco (left of Lupe Fiasco) and his older sister Africa Jaco on the far right. Photo by Tyger Ligon for The TRiiBE®

The commemorations and the belt ceremonies fall in line with the late Jaco’s history. Lupe’s dad grew up in the Robert Taylor Homes, a housing project torn down in 2007. That experience drove a teenaged Jaco to pursue martial arts as a way to counter the gangs. Later he served as a U.S. Army Green Beret in 1969. Years after he left the service, the Jaco family moved to the West Side, in 1988, near Madison Avenue and Albany Street. There, Shirley Jaco would raise Lupe and the rest of his nine siblings.

Karate and martial arts training figured heavily into the Jaco household. His entire family, including all his siblings, practiced martial arts growing up and remain avid practitioners. All of them are black belts and each of them was promoted with additional degrees during their father’s ceremony at the Stony Island Arts Bank. This aspect of Lupe’s life shines light on his music and his moves throughout life.

“We went to karate school three days a week, and all his students would come back to the house with us,” Lupe said. “So they would train at the crib. There was no difference between the house and the dojo. That’s all I knew was martial arts so everything in life got filtered through that. So whether it be the streets, whether it be school, my daily activities, the things I was interested in, the type of movies I would watch, everything was kind of filtered through the martial arts. [I] understood through that lens.” 

Sensei Jaco passed away in 2007 due to complications from heart failure and diabetes. Lupe would later pour his grief into his art. The resulting song was the passionate ode, “Fighters” which appeared on The Cool.

The Jaco patriarch owned and operated karate schools in various locations between Chicago and Harvey, IL. He had academies near 67th Street and Stony Island Boulevard, 75th Street and Yates Avenue, 35th Street and Michigan Ave, 57th and Vincennes Avenue, and 147th Street and Halsted Ave in Harvey. Lupe even recalls his father running community programs in the Bridgeview neighborhood and near 47th Street and Woodlawn Avenue.

Lupe Fiasco, as a child alongside his father, Gregory Jaco, who owned several martial arts schools in Chicago, is seen shaking hands with former Chicago Mayor Harold Washington. Photo by Tyger Ligon for The TRiiBE® with his dad.

When Lupe’s dad started a school, most kids in the neighborhood did not have to pay to take part. 

“The kids that could afford it? [They ] could afford it,” Lupe said of the sliding scale fees. “The kids who couldn’t afford it? They got their uniforms donated to them.”

Ayesha Jaco is Lupe’s sister and the beloved spoken word poet heard on many of his intros across his nine albums. She recalled growing up in their mother’s home, with so many books strewn throughout the house that friends would compare it to a “museum.” Their home was a haven from the violence and sex trafficking that plagued East Garfield Park at the time. Lupe’s older brother Harold “Huggy Behr” Perkins, according to Ayesha, lost 25 friends in 10 years in a half-block radius.

“You had all of these different elements pulling at you, but our parents grounded us in staying focused, staying on our path to be out of the way of that stuff so we were able to survive,”  Ayesha said. “But it was rough. But we had that grounded-ness, that awareness, that knowledge of self, that awareness to survive and how to be ourselves and be okay with that,”

She added that their parents instilled into all of their children discipline, follow through, and keeping their word. Vowing that everything they would do, they would do it to the best of their abilities.

Ayesha recounts being raised in a creative household where they were all encouraged to be themselves. As the elder sister to Lupe, she describes growing up with him as an “adventure” as he was always inquisitive, reading books, asking plenty of questions, loving to debate, and passionate about whatever he was into whether it was reading, martial arts, or winning a Street Fighter II World Championship Tournament.

His mother Shirley Jaco recalled Lupe reading all of the books around the house; craving to learn as much as he could. When he was 12, she said, he began to write his first raps, inspired by Oakland rap legend Too $hort.

“‘Boy, what you doing with this? I know you not gonna say this stuff you writing,’” she said while speaking of her initial reaction. “Then he elevated to what we have today.”

Lupe Fiasco’s sister, Ayesha Jaco spoke at Stony Island Arts Bank in celebration of Lupe Fiasco Day and honoring the martial arts legacy of their father, Gregory Jaco. Photo by Tyger Ligon for The TRiiBE®

Ayesha recalls Lupe having notebooks of raps and writing for hours in front of the TV.

“At first, we were like, ‘A rapper, seriously? You supposed to be a mad scientist,’” Ayesha Jaco said. “I didn’t know what to think at first, I knew he had always been around the arts and music all our lives, there was a love for it. But doing it? I didn’t think he would. But the wordplay, and the storytelling all come from his reading and watching Nova on Channel 11. Everything came from how he immersed himself as a child in books.”

Harold “Huggy Behr” Perkins was backstage at Lupe’s performance and proclamation ceremony at the Salt Shed. He was so happy, he ran out on stage with the rest of the fam.

“Aww man, you see I had to run out there, my knees almost went out [laughs],” said Perkins. “We’ve been wanting to do that for a long time. But for him to get that Lupe Fiasco Day, that’s…man. I’m finna go home to Dallas, happy than a motherf—cker, ‘cause we did that. That was a long time coming for him to get a piece of the city. Not saying they overlooked us because we still got Grammys, we still got plaques. It was just time for the city to represent one of the greats. I’ll never know the Commons, the Kanyes, the Lil Durks, and all that, but this guy here is something totally different.”

For Ayesha, it was a proud big sister moment after years of watching Lupe shine and navigate every obstacle throughout his 20-year career in hip hop.

“He’s always had an impact through his music, his activism, and his philanthropy,” she said. “It’s great to see the place that inspired him to recognize him and give him his own day.” 

After his show, The TRiiBE caught up with Lupe and spoke with him about his family history and growing up on the West Side.

This interview has been edited for length and clarity.

Could you describe the ways your family has been involved in the West Side over the years?

Lupe Fiasco: We always did coat drives. My mom was always the beacon for out west, like a safe haven for people of all walks of life. Gang members, drug dealers, homies from the hood, and older folks would always wind up in my mom’s house chilling, just talking and vibing. So, we’ve always had an open-door policy for people. My sister Ayesha, who’s the one who’s responsible for the Lupe Fiasco Day, the thing with my dad, all these other more municipal, bigger things, she’s been crushing it out west in terms of having an organization called West Side United. Even beyond charity work, [her mindset is] let’s build something, let’s make some profitable businesses, let’s get deeper into how you improve a community and give it a backbone and solve the actual problems. What does the long-term stuff look like? So, it’s part of the family tradition.

I interviewed your mom at the show. Was she the one who instilled your love of books?

Yeah, she kept the graphics around the house. My dad had a library too, though, for sure, he had a more [of] a Martial Arts library, kind of more esoteric stuff. But my mom, you know, she kept National Geographic. Our house was the window to the world. So it’s cool.

Was home an escape when you resided out west?

Our block was pretty cool; we’re on Madison and Albany. But behind [there], shit was f—cked up on both sides. So, GDs on this side, [Black] Souls on that side, [and the] Unknowns maybe a  little bit further down. But it was just something about that zone we were in. I mean, we have bullshit, we have prostitutes, and killers and shooting up the hallway. But it wasn’t on a daily, crazy basis. It was something that was kind of a rarity, actually, but it was right there. But then also, you’re going to my mom’s crib, and she still is kind of an intellectual culture woman who likes jazz and fine food, and she’s a chef and a seamstress.

Where did you get your sophistication and style from?

I ain’t got no style [laughs]. I don’t think I’m actually sophisticated, to be honest. I just what I like. But I’ll tell you like this; between my mom and my dad and the different areas of the city that we grew up in, we saw all the different areas in the city.  We always knew that the world was bigger than just our block. 

Lupe Fiasco is showcasing martial arts moves at Stony Island Arts Bank on Nov. 11, 2024. Photo by Tyger Ligon for The TRiiBE®

What are the biggest misconceptions people have about the West Side?

I mean, if you go anywhere with ill intentions, it’s gonna bite you in the ass. So, I mean, it just depends on why you going. In some areas it’s like, yeah, if you ain’t from here, don’t come here. It’s other areas that are a little bit more open and inviting. I just think it’s a legitimate question, like, why are you coming? If you’re coming to bring some bullshit, then don’t come. But if you come in with kind of an open mind, and come in to improve and better the place, that’s different. It’s the energy people bring.

What makes West Side artists ferocious lyrically and also so resilient?

It’s a different style, you know? I don’t think it’s any better than the South Side, North Side, or East Side. The West Side has a particular style based on what dudes wear. The style is intricate. In some cases, very quick verses. When I would be out south, it was slower, more like a traditional kind of boom bappy. But out west, it was very technical, very structured, meant to kind of have a certain bounce to it. So it’s just, like, a stylistic thing that happened out west.

For me, I was infatuated with West Side MCs because that’s where I’m from. And a big impact on me was JD Walker. You know, JD Walker was the reason I started to kind of really want to be a rapper, listening to “Macadocious,” “Bogus Bangin,’” and some others, and that’s all West Side shit. For me, that was just the impetus. So I guess I just inherited elements of that style. And as I come up, you got other cats kind of building off me. So you got Saba and some other homies just building off what came before.

Do you think the hyper attention on gun violence within Chicago hip hop takes away attention from lyricism?

I don’t know, to keep it a buck. I mean, I think Chicago has established itself as being a city with a high level of lyricism. From Rhymefest to Common, to Kanye, to myself, to Chance [the Rapper], right to Vic [Mensa], Chi-Town dudes is nice.

I asked that because it seems like the younger lyricists from Chicago are having a much harder time getting recognized by the mainstream, compared to Drill rappers.

I mean, yeah. I was going to say that lyricism isn’t as exciting as killing a nigga. It never will be. It never has been. If there were two doors and it was like ‘yo, it’s a fight behind this door and it’s a book reading behind this door,’ how many people you think are gonna go into the book reading? It’s a boxing ring on this side and a library behind this door. Man, that library door gonna be dusty as hell.

If you think that lyricism is going to compete with violence, that ain’t finna happen. Not in any serious, competitive way. You can blend it. But even still, there’s way more stickiness to seeing something pop off than hearing somebody rap about quasars and lasers.

For a lot of blogs and vlogs online, it’s about how many people you shot. A lot of rising rappers get interviews because of their gang affiliations and crimes rather than their music.

Rap has been super violent. Rap was super violent in the 90s. Part of that appeal was that. Hip Hop as a whole wouldn’t be in the space and at the levels that it is if it wasn’t violent. It persists because it has teeth, right? It does have an aggression to it. It will beat your ass, right?

What kept you away from being a gangster rapper?

I was a gangster rapper [laughs].

Yeah, but you weren’t banging on wax.

It was a decision to be made. My partner, Chill, caught a case which he got convicted for. And there were a lot of layers and pieces and parts to the story and it just landed on, like, look, we’re putting this album out. What do we want to be known for? What do we want to put out to the world? You know, do you want to put out this record you did with Three 6 Mafia? Do you want to put out this record you did with whomever, talking about beating up niggas and shooting? Or do you want to put out “Kick, Push,” a song about skateboarding. 

Just because you’re a Drill rapper, that don’t mean that the only thing you rap about is Drilling. You can make songs about anything, right? And they probably do. But I just made the decision… it’s gonna be uplifting, it’s gonna be different, and it’s gonna have a message to it, to push and inspire. And you could do both!

In 2007, “Kick, Push” by Lupe Fiasco received Grammy nominations for Best Rap Solo Performance and Best Rap Song. Graphic by Ash Lane for The TRiiBE®

I’m still a gangster ass nigga on the flip side, right? And that’s just by design. Everybody’s in the gang! Everybody’s linked up and connected in some way, by some degree, to somebody who’s doing some shit that they shouldn’t be doing, right? But that don’t mean that’s the only thing that they do.

You listen to “Kick, Push,” it’s some hood shit – especially if you listen to “Kick, Push II.” You get into who these people are: niggas is on dope and mom on dope and kids, it’s all kinds of [stuff] happening, right? But skateboarding their way out, right? It’s the thing that gives them hope. It gives them a culture. It gives them a group of friends to kind of look into. It gives them a world that they can kind of be in and control and be safe and have fun, and then do some other things in the midst, but it’s still taking place in the hood.

What comes to mind when you just hear a whole generation of kids now finding fun in gun violence?

Niggas have been playing with guns since we was kids. Everybody did that.  Everybody want to fight. Everybody played Street Fighter. Super Mario Brothers, yeah, that’s violent! What you doing? You stomping on people, right? Setting niggas on fire, yeah, running into the money, getting to the bag, right? 

But we don’t look at it like that. We don’t really look at the impact of that. We’ve been kind of courted and trained in a certain way to be, if not actively violent, passively violent. I mean Drill music is the worst shit to me, because it’s literally happening. Niggas is telling you what the f—ck they did last night. But I look at shit like, Call of Duty (COD), right? And you just see a regular person just sit there, like, ‘we got killers shoot him in the head.’ 

Do I think everybody’s gonna be able to live out those [Grand Theft Auto video game] fantasies? No. Do I think everybody’s capable of those fantasies? No. Do I think that’s an excuse to let that slide? No. Can I actually stop it and control it in any way? No. I’m not going to stop any kid from playing COD, especially somebody else’s kid.

If we actually try to solve the problem, then that’s different from critiquing the problem with my thoughts about the problem. But ain’t no gun factory out west, right? If you really want to solve the problem, how come we’re not protesting gun factories in Georgia?

So, what comes to mind when people say, “Lupe, you saved my life!” Or “Lupe, your music helped me get through college.”

I mean, you the one who had to do the work! I didn’t come in and do your homework for you. Like I said, I appreciate it. We were going to put music into the world to uplift and inspire versus music that tore down. That’s what we did. And it worked. 

The post How Lupe Fiasco became immortalized as Chicago’s rap sensei appeared first on The TRiiBE.

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