Enyia, who was little known until Chance the Rapper and Kanye West supported her, is now among the high-profile candidates in a crowded field

Among the sepia portraits on the wall of Chicago’s past mayors in an upscale steakhouse, Amara Enyia’s supporters unveiled a photo of the 35-year-old Nigerian-American mayoral candidate last week.

“It’s in color … no beard … not bald … not white!” called out people from the crowd. They were at the Chop House for a fundraiser headlined by the Grammy-winning musician and activist Chance the Rapper, drawing a mix of celebrities, grassroots leaders and regular people new to politics.

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Enyia, a policy analyst and lawyer, was little-known by the political establishment until this fall, when Chance (full name Chancellor Bennett) and hip-hop star Kanye West threw their support, and dollars, behind her. Now Enyia is among the higher-profile candidates in a crowded field of more than 15 candidates, which includes political veterans like Bill Daley, brother and son of mayors who ran Chicago for a total of 43 years.

When the outgoing mayor, Rahm Emanuel, ran for re-election in 2015, Enyia was the first candidate to announce a run against him. She wasn’t regarded as a realistic contender then, and she would still be considered a longshot candidate in the 26 February 2019 race. But after two years of election results that defied predictions nationwide, Enyia and her supporters think that her ability to tap into underrepresented communities, and her support from the prominent rappers, gives her a chance to replace Emanuel, who announced in September he would not seek re-election.

Enyia’s first test will come after Thanksgiving, when it will be clear if she has enough campaign petition signatures to even get on the ballot. Candidates must submit at least 12,500 signatures by 26 November, but double that number is typically necessary to survive legal challenges from opponents.

“She is able to get media attention and the money from rappers to pay off her campaign debts and have some working capital,” said University of Illinois political scientist Dick Simpson, a former alderman who has endorsed another candidate in the race. “But it’s still in the tens of thousands of dollars; the front-tier candidates have in hand about a million dollars at this stage.”

Facebook Twitter Pinterest Chance the Rapper, who has endorsed Amara Enyia for mayor of Chicago, at a news conference on 16 October at City Hall as Enyia listens. Photograph: Joshua Lott/Getty Images

But last week’s fundraiser, where Chance and Enyia hosted a $2,000-a-plate “intimate dinner” and then joined the cheering crowd in the bar, felt to attendees like an embodiment of shifting political winds in the city. There were young people who said they had not voted before, many of them from struggling South and West side neighborhoods where disillusionment with elected officials runs high.

“I didn’t believe in politics until Amara,” said Tree, 24, who declined to give his last name. Inspired by Enyia, he voted for the first time in this month’s midterm elections.

Whoever wins office will face the same challenges that plagued Emanuel throughout his tenure, including high rates of gun violence, a scandal-plagued police department, struggling underfunded public schools, longstanding segregation and vast disparities in wealth between neighborhoods.

Along with Bill Daley, the field of mayoral contenders includes two former Chicago Public Schools officials, the powerful county board president, a Black Lives Matter activist, a former state representative, and Lori Lightfoot, the woman tasked by Emanuel with reforming the city’s police department after the high-profile killing of teen Laquan McDonald by an officer recently convicted of murder. The field also includes Garry McCarthy, who was police superintendent at the time of the murder. In all, the race features a racially diverse mix of political insiders and rabble-rousers.

Enyia is the daughter of Nigerian dissidents who settled in the Chicago suburbs in the 1970s and continued to be active in their country’s politics. She speaks five languages and competes in Ironman triathlons. Her campaign has included running on neighborhood streets, joining would-be constituents in one- and three-mile jogs.

In 2009 Enyia was hired by then Mayor Richard M Daley as a policy analyst, and she currently serves as executive director of a neighborhood chamber of commerce on Chicago’s West Side, where she also lives, a largely African American area struggling with violence and disinvestment.

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“I have a perspective other candidates don’t have,” said Enyia. “I see the guys who are part of the unemployed, dealing with addiction, the lack of access to mental health resources, I see that all right in my building.”

Enyia said she got a text from Chance “out of the blue”, asking to talk about her vision. Though they hadn’t previously talked, they’d been in the same political spaces in Chicago, including around the “No Cop Academy” grassroots movement opposing city funds for a new police training center.

While Enyia said her musical tastes are generally more “old school” than Chance’s, she admired his community involvement – including donating more than $1m to Chicago public schools through his charity.

“He said he’d been a fan of mine for a long time,” Enyia said. “I was a fan of his too, because he had a track record of walking the walk.”

Facebook Twitter Pinterest Hip-hop artist Chance the Rapper during Grammy awards in Los Angeles on 12 February 2017. Photograph: Christopher Polk/Getty Images for Naras

Chance told the crowd at the Chop House that when he surveyed the “54,000 people” running for mayor, “I came across Amara. Who is just it. It was staring me right in the face … this is our Harold Washington” – the city’s first and only black mayor, elected in 1983.

At the fundraiser and at a campaign stop earlier that afternoon at the University of Illinois at Chicago, students said they found out about Enyia because of Chance, and were won over once they learned more about her life and policy platforms.

“It’s not just because she’s a black woman, she really wants to change Chicago,” said Terri Adams, 28, a friend of Chance’s who is especially impressed by Enyia’s focus on investing in public schools.

Enyia advocates for an elected school board, a public bank, restorative justice, a boom in cooperative enterprises and greatly increased government transparency. She’s campaigned around the city, spending quality time in neighborhoods that residents say Emanuel and other candidates in the race ignore.

Chance’s father, Ken Bennett, was a top adviser to Emanuel, and was also an aide to former president Barack Obama. He is now involved in the mayoral campaign for the Cook county board president, Toni Preckwinkle, a longtime political insider. “He loves his dad but they have different ideas of what the city really needs,” said Enyia.

Kanye West’s support for Enyia is not as smooth a fit, considering his controversial bond with Donald Trump and recent erratic remarks, including his widely criticised claim that slavery was a choice.

“It’s no mystery where I am on the political spectrum,” said Enyia. While that’s a different place than West occupies, “he’s open to different policies and different points of view, and I’m OK with that”.

West first donated $73,540 to Enyia in October, the exact amount needed to cover outstanding debt from her 2015 run. A week later, West donated $126,460 to Enyia around the same time he announced on Twitter that he was “distancing” himself from politics. Board of elections records show no donations from Chance, but Enyia says his public support has been invaluable.

Community organizer Jose Requena, 32, is among the Enyia supporters who think West could create challenges for her campaign. He described Chance as “what my generation hoped Kanye West would be”. But he also sees Enyia’s embrace of West as an example of her ability to reach across demographics.

“She has a wide appeal to millennials who are becoming very political, and if she can also get that Generation Z, and [people of all ages who are] so disenfranchised, she could dramatically change the politics of the city,” said Requena.