Chance the Rapper, Cops and the Chicago Way: Talking the Windy City Mayoral Race With Amara Enyia

Chance the Rapper listens to Chicago mayoral candidate Amara Enyia speak during a news conference at City Hall on Tuesday, October 16, 2018 in Chicago, Illinois. Chance the Rapper announced his endorsement for Enyia and said she is the best candidate for Chicago.
Chance the Rapper listens to Chicago mayoral candidate Amara Enyia speak during a news conference at City Hall on Tuesday, October 16, 2018 in Chicago, Illinois. Chance the Rapper announced his endorsement for Enyia and said she is the best candidate for Chicago.
Photo: Joshua Lott (Getty Images)

Chicago has had a rough couple of weeks when it comes to the American news cycle. The Night King decided to make the city his vacation spot, Jussie Smollett and the Chicago Police Department have been in a fight to see who sounds the least credible, and R. Kelly’s latest arrest is a reminder of why it’s taken so long for the alleged predator to be brought to justice (again) to begin with.


Yet, in the midst of the national coverage of Chicago, there’s scarcely been a mention of the biggest thing happening in the city: a huge mayoral primary on Tuesday, Feb. 26, that could likely change the face of Chicago more than any TMZ-style story has over the last few weeks.

There is a field of 14 Democratic candidates (the only viable party for mayor) and it features three African-American women; 71-year-old Cook County Board President Toni Preckwinkle; 56-year-old former Chicago Police Board President Lori Lightfoot; and 35-year-old community activist and lawyer, Amara Enyia. Two of them, Preckwinkle and Lightfoot, are in a three way tie at 14 percent heading into Election Day with Chicago political scion Bill Daley. While three black women may seem like a sign of progress for the Windy City, according to Enyia, black Chicago is still in a very precarious place.

“Chicago has been a top three city in population loss,” Enyia said during an interview with The Root in her cozy campaign office during a brisk evening. “We’ve lost over 250,000 black residents in the last 15 years alone.”

To put that into perspective, Chicago has lost roughly a Cleveland- or Pittsburgh-sized number of black folks in the last decade and a half. Some moved to the suburbs, but many are leaving Chicagoland entirely, heading to Houston or Phoenix or Atlanta. With that loss of population comes a loss of political power in the city. Why is this happening? It might have something to do with the “Chicago Way” that Amara Enyia is fighting against in her campaign.

When I first saw Amara Enyia, I was eating at an old-school deli shop next to her campaign office across from DePaul University. Incredibly tall and poised, she walked into the same spot with what appeared to be a body guard, and she looked like she was doing cosplay of Michelle Obama with the Secret Service. Enyia was only halfway through her order when a DePaul University student walked up to her, praising her campaign from 2015 and saying he was voting for her again. The candidate smiled and bantered for a bit before even noticing me chowing down on my pre-interview cheesesteak. She complimented my sandwich choice, betraying a natural way around people that fits her profile as a long-term activist with deep passion for the city. You’d want Amara Enyia as your neighbor, friend, business partner or mayor, and yet in many ways she is a Chicago dream that has yet to be realized.

While Chicago isn’t the mobbed-up paradise you see in the movies, the city is incredibly politically top heavy. As I spoke to campaign staffers in her office, I kept hearing references to “the Chicago Way,” which, quite honestly, I thought was something people only said in movies or mawkish CBS series’ about cops or firemen. When I asked Enyia about it, she first chuckled and then made it clear the Chicago Way is a real thing.


“How does that phrase go?....Nobody wants somebody that nobody sent for,” she said. “You have to be selected. You have to kiss the ring in order to be moved through the system, in order to be known [In Chicago].”

Enyia is definitely not someone that anybody linked to Chicago politics has “sent for.” She’s the consummate outsider, a millennial activist with Nigerian immigrant parents who got her bachelor’s, law degree and doctorate from the University of Illinois. She’s running on a very progressive platform with policies like creating a Chicago public bank; allowing those jailed on old marijuana drug charges to get a foot hold into the new legal market; and a “Ban the Boot” program where people are given the chance to pay off car and boot fines with community service if they can’t afford to pay in cash.


“Chicago stifles innovation,” she said during a long monologue about opportunities for young people in the city.

If the only way you can make a difference in Chicago politics is to be ushered in by powerful families like the Daleys (who have already had a father and a son run the city in the last 40 years and another Daley is in a three-way tie to be the next mayor), how does the Enyia campaign plan on countering that? Through the power of hip-hop.


Chicago, perhaps more than any other America city, has a history of politically active rappers. Common was a long-term surrogate of the Obama campaign. In 2011, I interviewed rapper and producer Rhymefest, who ran unsuccessfully for Chicago’s Ward 20 city council seat; most recently, Chance the Rapper and, yes, even Kanye have been involved in politics, not just in words but with their cash as well. What the Enyia campaign couldn’t do through name recognition or deep city Chicago Way contacts, they are doing with the newest power pillars in the city.

“My first conversation with [Kanye] happened out of the blue, he called my cell phone out of the blue...and said like…Hi?” she chuckled.


“He’d heard about my work, and it was actually a visioning conversation. He has all of these businesses, fashion, shoes, what does it look like to have these factors back in Chicago—for working people—he also talked a lot about housing. It was one of the most out-of-the-box conversations I’ve had in a long time.

Initially, Enyia was apprehensive about Kanye’s politics, especially given his off-brand praise of Trump, Blexit, and half a dozen other problematic things he’s done over the last few years. However, in the end, she sensed that he really loved the city of Chicago, the South Side that raised him, and she could make an alliance with someone she didn’t always agree with so long as it helped the city.


“He felt in his spirit that my campaign was what Chicago needs. That was how it started, it definitely gave me a level of notoriety.”

The same goes for her relationship with Chance the Rapper. Chance has been a huge activist in Chicago, donating millions of his own dollars to public schools and mental health programs.


“He was at many of the same organizing spaces as me, but our paths had never directly crossed,” Enyia said.

Eventually, Chance met Enyia after a city council meeting for the “No Cop Academy” movement. No Cop Academy is a collection of 85 community groups in Chicago proposing that instead of spending $95 million on a new police academy for the city, that money be used to reopen closed schools and other projects of community investment. Enyia and Chance vibed on the things that needed to be done to improve the lives of Chicagoans. The rapper, who infused his lyrics with bible quotes, has not only campaigned for Eniya but donated $400,000 as well.


“He [Chance] has lent a level of visibility to the campaign nationally—and he’s valuable because his support is substantive, it’s not just, ‘I like this person and vote for them.’ It’s ‘we’ve been in some of the same trenches’ on these issues.”

The Amara Enyia campaign may be a longshot. The polls conducted by local stations 24 hours before the election don’t place her in the top two spots, the candidates who would potentially meet in a runoff in April. However, polling for the race has also been scattered and turnout is expected to be low, which opens the chance for an outsider with a good ground organization to stage an upset.


Amara Enyia in the mayor’s mansion might just create a Chicago Way that all residents can participate in.



I want to move back to Chicago just so I can vote for Amara Enyia