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As the resident Chicagoan on The Root’s staff, it’s safe to say I keep an eye on the city’s resident talents—including Chance the Rapper and problematic prodigal son Kanye. Now, I’m thinking I need to get out more—or, at least, take a Lyft—since apparently, hip-hop’s favorite number-wearing philanthropist has been taking it to the streets, using Lyft’s Round Up and Donate feature to help his Social Works charity raise funds for Chicago Public Schools.

Chauffeuring unsuspecting hip hop fans through our fair city is fun to watch, but it’s these types of socially-conscious antics that have people speculating on whether Chance is considering a political run—well, that and his own cryptic tweets on Monday afternoon, announcing a Tuesday morning press conference regarding Chicago’s mayoral race.

As the Chicago Sun-Times noted, “I’m thinkin’ maybe I should” is actually a portion of a Chance lyric from 2015 “Somewhere in Paradise” that says, in full: “They screaming Chano for mayor, I’m thinking maybe I should.” The lyrics are also featured on the homepage of the Chano 4 Mayor website, which has no affiliation with the rapper, but was started in 2017 to encourage him to run against Chicago’s current mayor, Rahm Emanuel.

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Hmmm...what does it all mean?

Well, with Emanuel announcing in September he will not be seeking reelection for a third term, the race is now wide open, with several activist candidates in the mix. As the Sun-Times reported, Chance is unlikely to be announcing his own run, but has been closely linked to one of the candidates already in the running, community activist Ja’Mal Green, since the two were in youth programs together as adolescents.

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But several sources have speculated that Chance will endorse another mayoral hopeful on Tuesday, Amara Enyia, a Garfield Park activist and director of the Austin Chamber of Commerce who previously ran in 2014, dropping out in favor of Alderman Bob Fioretti.

Notably, Ja’Mal Green told the Sun-Times in August he was running because he couldn’t convince Chance’s father, Emanuel aide and longtime-community organizer Ken Bennett, to run against the incumbent. Green has scheduled his own press conference for 10:30 a.m. CDT on Tuesday; 30 minutes after Chance’s scheduled press conference.

Updated: October 16, 2018, 12:14 p.m. ET: As predicted, Chance has thrown his support behind Chicago mayoral candidate Amara Enyia. As reported by ABC 7, he said:

“Amara and I share values and a vision for Chicago that includes equitable education for our kids, reforming our criminal justice system, and bringing new kinds of economic opportunities to our communities without causing displacement,” Chance said. “I am proud to stand with her as we work toward bringing new leadership to City Hall.’”