Chance the Rapper and journalist Adrienne Samuels Gibbs at "In Sight Out," a Pitchfork podcast series taped at the Museum of Contemporary Art in Chicago//photo by Jeremy Lawson

It is no secret that Chance the Rapper loves his hometown of Chicago, but as with many love affairs, the relationship has had its share of ups and downs – hurt and healing.

The Chatham-bred rapper expressed his anger surrounding the Chicago Board of Education’s recent unanimous vote to close four Englewood high schools and more during a sit-down interview with former Ebony Magazine senior editor and current contributor Adrienne Samuels Gibbs. The conversation was part of “In Sight Out,” a podcast discussion series between artists and journalists that is curated by Pitchfork Media.

Chance, born Chancellor Bennett, called Monday night’s chat with Gibbs a “healing experience.” The two had worked together before on Ebony Magazine’s June 2017 issue – which featured a hatless Chance on the cover and Gibbs behind the pen. During this reunion, Chance and Gibbs discussed everything from philanthropy and activism to Chicago politics and, of course, his music, including a rumored project with wunderkind actor/writer/artist Donald Glover, a.k.a. Childish Gambino.

Here are some of the highlights from their talk.

On the CPS Board’s unanimous vote to close four Englewood neighborhood schools

I feel cheated. I feel angry. I feel vengeful. You grow up feeling like you are fighting against ‘the Man,’ or fighting this faceless entity of people who are out to get you. But these people have names, and Rahm is [one of those people], and there is no way to hide it.”

“This is the third group [of school closings] since 2013. The truth is all of these schools have a few similarities, and it is not like we have to dance around it.”

“I am tired of just trying to rock with Democrats, because I am supposed to be a Democrat. There is nobody coming out and saying, ‘I see the inequality. I see the inequities. I see the unfairness, the violations of our city. I see the scathing Department of Justice review on our police department, the same one that murdered Fred Hampton.’”

“I see that this is a fucked up system and this is me inserting myself into it to change it all. I don’t want to be ‘the one.’ [ed. note: Chance is referring to his disinterest in becoming a politician]. But I want to stand behind whoever that is and whoever has that voice.”

On raising and donating millions of dollars to Chicago Public Schools

There were all of these ideas to donate to different organizations, but there are all of these different places the money could go and I knew we were in the budget crisis and there were so many city functions that weren’t being properly funded and I figured I could put something in the city that would help.”

“But the money thing wasn’t as important as all of the waves it made. I got to see how CPS functions. I got to learn so much stuff: how we are the only [school] district in the state that doesn’t have an elected school board. I got to see how different the facilities are on the South and West sides of the city from the ones on the North Side.”

“I got to really connect with these principals and how they are like the CEOs of these schools working with tiny budgets and finding out in the middle of the school year that their budgets are getting slashed in half, and [each principal is stuck] trying to figure out how to pay all of their teachers, and how their schools are going to have supplies and also being hung out to dry when things don’t work out.”

Photo by Jeremy Lawson//Museum of Contemporary Art

On learning from Kanye West and his creative process

[Kanye] showed me how to multitask and how to use the studio as more than just a recording space. When he was working on The Life of Pablo, that was the first time I got to be around him in music not at some type of event. He really believed in me and would do a lot of cool rants to people about how I was the Steph Curry of rap. That was one of the coolest things.”

“[Kanye] rents the whole studio. Usually, professional studios are multiple floors, multiple rooms, and he would fill up these rooms with people working on different projects. The reason I use my studio as an office is from watching him do the same thing. There would be rooms with people working on three different songs [for] the same album, but also another room with just pictures and [clothing] samples of different materials all over the walls. There were all of these people on laptops. I don’t know what they were working on but one woman back there was a producer on ‘The Lego Movie’ and she was having a conversation with a dude who was, get this, a magician. They were having a conversation on how to make Kanye West disappear at a show.

On winning three Grammy awards in 2017 for best new artist, best rap performance and best rap album (Coloring Book), and opening the box of awards with his daughter

I just thought it would be cool for someone to say I got a Grammy without a label. I got them [in the mail] and I’m holding a Grammy that probably weighs around 7 to 10 pounds in one hand and my daughter, who is about 30 pounds, in the other hand. My daughter doesn’t know what a Grammy is, but she could feel that I was happy and she was hugging me and congratulating me and I was thinking about all of the nights I slept in the studio that I could’ve been with my baby and how much pressure I had put on myself to get this done.”

“I had put so much effort into it – to really just stand there as a scale for a moment and feel the weight of my daughter and how much more important that was and it broke me down for a second. I was like, ‘Cut off the camera for a second. I’m about to start crying.’”

On comedienne Mo’Nique and her fight for equal pay

You see everyone talking about equal pay and [how] this actress needs to take less so that this actress can get more, but Mo’Nique comes out and says, ‘I know my worth,’ and people are slamming her.”

“I see how deeply embedded racism is and sexism and vice-versa and understand that I can’t really call myself free or feel like I am liberated unless Black women are liberated. I can’t feel like I am doing something for people if I can’t understand how many double standards there are and then how many different dimensions they work in and [that] they all thrive off of white supremacy, toxic masculinity [and] patriarchy.”

“I am with Mo’Nique.”

On his rumored mixtape with Childish Gambino, sketches on Saturday Night Live and other creative projects

The truth is: me and Donald [Glover] perpetuated a story of a mixtape for a long time without ever working on it. I’ll say [that] we did link up in Atlanta not that long ago and started working on some tracks and they’re amazing. They are going to touch people.”

“[‘Shot in the Dark’] really spoke to me. When people try to show Chicago culture and show you Black people, they show you literally the worst stories and the worst telling of them, but this movie was authentic West Side – like, parties outside on the block and the dialect. This movie just really gave that air to breathe and I thought it was perfect timing with the $90-plus million cop academy [being built] right around the corner from Orr. [ed. note: Chance and Dwyane Wade are the executive producers of “Shot in the Dark,” a documentary about Orr High School’s basketball team.]

“I have pretty thick skin, but niggas be calling me an ‘industry plant,’ and it really ticks me off. But I don’t be sounding off. I don’t get on Twitter talking all crazy. But some niggas tried to say that one reason they didn’t trust my authenticity, or one reason they didn’t believe I could do it without the machine, was because I was on Saturday Night Live. For me, it was a personal goal. A lot of people who are on SNL are there because they are promoting something. They’re not pitching sketches.

On possibly moving away from Chicago

I’m here, I’m posted. I’m not going anywhere. I’m gonna live in Chicago till the day I die. I’m gonna leave every once in a while, I’m gonna travel, I’m gonna do some tours – get that bag. Then I’m gonna lobby for y’all”

** This interview has been edited and condensed in some places for clarity.