Andre Vasquez had never run for public office before launching his campaign for 40th Ward alderman in April, but he’s been in plenty of battles. As a Lane Tech student in the mid-90s, he’d spend his weekends crisscrossing Navy Pier, entering impromptu cyphers where he’d freestyle against other ambitious young rappers from all over Chicago. Vasquez says he competed in more than 1,000 battles and lost only seven times—though admittedly that’s by his own count. He says that someone who saw him in action called him Optimus Prime, in homage to the Transformers franchise’s head Autobot—he thinks because of his skill at mimicking popular rappers. The name stuck, and as Vasquez grew into a career in hip-hop, he called himself Prime.

The 40th Ward covers pieces of several north-side neighborhoods—Lincoln Square, Edgewater, Andersonville, and Budlong Woods among them. (Rosehill Cemetery takes up a large chunk of the ward, but the dead are a notoriously risky electorate to court.) Jon Cignarale, who co-owns Over Easy Cafe near Lawrence and Damen, saw his business get redrawn into the 40th Ward in 2015; prior to that, he’d built a relationship with 47th Ward alderman Ameya Pawar. “I used to see him once a month, he’d come in—anytime I needed anything, it was real quick,” Cignarale says. “O’Connor, not so much—it’s old-school.”

“It’s different when it’s music or hip-hop—people go, ‘I like the music, that’s why we’re coming out in a crowd,’” Vasquez says. “But when you’re talking about these issues, and you get people that are invested that are throwing down and dedicating so much time, it just speaks volumes.”

One of the few battles Vasquez lost took place in a Mexican restaurant across the street from the Congress Theater. DJ and producer Juvenal “PNS” Robles judged the competition and gave Vasquez the L. “He could read an opponent, and it’s funny ’cause I think it still fits him today,” Robles says. “As opposed to regular battle guys, who’d just go in for insults and the cheap joke, he’d go for nuance.”

In 2002, the Molemen released the Prime 12-inch Madman and a CD-R called The Optimus, the debut by Prime’s crew the Scam Artists, which also included Atomz, rappers Verbal and Robust, and producer Qwel (who eventually became a Moleman). Within a year or so, however, Vasquez started getting frustrated by his position in the Molemen. “I kept seeing my value as being, like, ‘Oh, [I’m] the intern, I’m gonna go do this,’” he says. “It took a while for me, as a person, to be able to separate myself from what I was accomplishing, and understanding that I have value regardless of that. I think I was going through internal stuff, and at that point we kind of parted ways.”

Music was never enough to support Vasquez by itself—as he got established in hip-hop, he also moved up in the world of retail. “I had gone from first being a janitor at Kids ‘R’ Us at the Addison Mall to working at record stores to selling cell phones to running my own AT&T store on Chicago and Rush,” he says. His day jobs helped him pay for studio time and beats, but they also provided him a cushion for a future beyond rap. “The way I thought about it was, ‘If my parents came to this country and I’m just this rapper that lives in the basement when they’re older, then I’ve failed,’” he says. “It caused me to make a lot of calculations.”