Aldermanic candidate Andre Vasquez gathers signatures for his ballot petition in January. Credit: Deana Rutherford

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.

In the late 90s, he went on to become a member of venerable underground hip-hop collective the Molemen. He toured with Atmosphere in the early aughts, appeared on HBO’s Blaze Battle and MTV’s Direct Effect in 2000, and recorded with KRS-One in 2008. He’s happy to tell visitors to his campaign office about the time he coaxed Wyclef Jean into a cypher after spotting him in the bathroom at the House of Blues, or the time he improvised an entire set opening for Noreaga after his DJ forgot the backing tracks, or the time he freestyled with Guru from Gang Starr and Juice at Metro. But about eight years ago, Vasquez, who’s now 39, decided he wanted out. “I remember going to the bars and the clubs and being like, ‘I don’t want to be the over-30 guy at the club when all the kids are doing their thing,'” he says. “It started feeling very repetitive. I’m like, ‘All right, let me see what the rest of life looks like.'”

Vasquez never considered getting involved in politics until the 2016 presidential primaries, when he became a fan of Bernie Sanders. He went to bat for Bernie on social media, then knocked on doors in Iowa. In March 2016, he threw a fund-raiser at the Wild Hare called Bern Fest, and its success led him to get involved in community organizing that had nothing to do with Bernie. He’s now the chair for the North Chapter of Reclaim Chicago, a progressive PAC that aspires to make local politics more equitable—that is, he’s the lead volunteer for the group’s organizing work on the north side.

Reclaim endorsed Vasquez shortly after he announced his bid to become 40th Ward alderman. He’s one of four candidates challenging incumbent Patrick O’Connor, who’s held the seat for more than three decades—and who recently replaced the embattled Ed Burke, in whose footsteps he’s long walked, as chair of the City Council’s Finance Committee. O’Connor is Emanuel’s floor leader in the council, a role he also played under the younger Daley. After he won his first aldermanic election in 1983, he aligned himself with Burke and Tenth Ward alderman Ed Vrdolyak, who led a council bloc that fought Mayor Harold Washington as stubbornly and viciously as congressional Republicans fought Obama. O’Connor represents the kind of old-school political power that Vasquez and the other challengers—Maggie O’Keefe, Dianne Daleiden, and Ugo Okere—position themselves as alternatives to.

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.”

Cignarale doesn’t know much about O’Connor and hasn’t heard of any of the challengers. But he’s got a couple issues he’d like any alderman to deal with—including snow removal, of course, and an increase in crime that he’s heard about. “I don’t really follow that many of the issues, but in general, how about plowing?” Cignarale says. “We used to have it. Now we do it all ourselves.”

A mechanic named Pete at an auto-body shop near Foster and Western (he declined to give his last name) has his concerns too. “Everything—violence, homeless people, everything,” he says. But he can’t name the 40th Ward alderman—perhaps a less unusual phenomenon here than elsewhere in Chicago, given the low profile O’Connor keeps in the ward. His opponents all criticize him for his disconnection from the community and his failure to listen to its residents, and the Sun-Times even repeated those complaints while endorsing him earlier this month.

“I really don’t care, to be honest,” Pete says. He doesn’t know who’s running for alderman either, and he won’t be voting. “Our votes don’t count for nothing,” he says. “We’re just people—we’re just pawns in this world. Our votes don’t matter.” That’s an attitude Vasquez knows well. “Hip-hop music taught some of us to be absolutely cynical, to believe that our votes don’t mean anything, that we don’t understand and aren’t welcome to that world,” he says.

Vasquez has learned to reach past such cynicism, and he believes he’s got the best chance against O’Connor. He’s about as far from the Chicago machine as aldermanic candidates get: he’s a member of the Democratic Socialists of America, and he supports a Civilian Police Accountability Commission (an idea pushed by fellow DSA member and 35th Ward alderman Carlos Ramirez-Rosa). He’s in favor of an elected school board, and he wants to strengthen the Affordable Requirements Ordinance, requiring developers to build 30 percent of new units as affordable housing and closing loopholes that allow them to build those units elsewhere or not at all.

“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.”

Andre Vasquez talks politics with a potential constituent at Isabella Bakery (1659 W. Foster) in January.Credit: Deana Rutherford

In the late 70s, Vasquez’s parents emigrated from Guatemala to Illinois, where they married. His father repaired shoes downtown and eventually found a job making orthotics for Lurie Children’s Hospital; his mother worked the night shift at an envelope factory, then became a housekeeper. Vasquez was born in 1979, and he and his younger brother grew up in southern Bucktown. “There were Latin Kings on the street, so my parents kept me inside and sheltered,” he says. “But also because they were undocumented, they were concerned that anything I would get into might perhaps put them in a situation where they could get deported.” He spent a lot of time reading alone at home. “Because my parents kept me in that space, books and everything were my way out of it,” he says. He devoured science fiction and comics—and as an adult, he’d name his son Parker because of his love for Spider-Man.

During Vasquez’s childhood, his family got priced out of four different neighborhoods. They left Bucktown for Humboldt Park, then moved to Roscoe Village, Avondale, and finally Irving Park East—all areas to the south and west of the 40th Ward, which extends north-south roughly from Devon to Lawrence and east-west from Clark to Kedzie. Vasquez believes his relative rootlessness as a kid taught him the value of being connected to a place and its people. “It allowed me the opportunity to see what it’s like feeling separated and not part of a larger community,” he says. “So I’m really invested in trying to build community at every possible instance.”

As a freshman at Lane Tech in 1993, Vasquez found his first real community through hip-hop. Rap fans at the school would form cyphers between classes. “I went from writing my first little raps and trying them out in front of people to really working on my freestyle skills, and that got me notoriety,” he says. “And as somebody who had never been the center of attention, it just blew my sense of self up—which is sometimes a little bit too much when you’re a battle rapper. But considering what I had come from and feeling like nobody, I think it provided a good counterbalance.”

In high school, Vasquez aspired to be an English teacher, and rapping engaged his writing skills. “I’ve always been really . . . excited is a weird word to say, but really interested and intrigued in how people put words together,” he says. “Hip-hop allows you to create these Rubik’s Cubes of wordplay.” Soon Vasquez got a taste for battle rap, and every day after school, he’d post up near the edge of campus on the corner of Addison and Western, dressing down challengers in front of dozens of spectators. On weekends, he took his hunt for opponents to Navy Pier. “That got me a lot of notoriety citywide, also because I was one of the very few brown kids that were doing it,” he says. “What they would say is, ‘Who’s that white boy?'”

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.”

Vasquez on the mike at a rap battle in 2003Credit: Courtesy of Andre Vasquez

Robles became an important figure in Vasquez’s development as a rapper—thanks to his position in the Molemen, one of the city’s longest-running DJ and production collectives, he provided the younger man with an entry point into the local hip-hop scene. Founded in 1989 by producers Ed “Panik” Zamudio and Alberto “Mixx Massacre” Espinosa and rapper Donald “Vakill” Mason, the Molemen had become a dominant force in Chicago’s underground rap community by the mid-90s, when Robles joined. He frequently DJed at local hip-hop events, and Vasquez offered his services. “I used to carry records for him when I was like 16, 17, to get into Double Door to get on the mike,” Vasquez says. He bonded with several core members of the Molemen especially easily because of their shared heritage. “I met Panik through his brother, Visual. I think because we’re all Latino too, it was easy to kind of identify, and they were just like, ‘Yeah, we’re gonna bro you, so come on board.'”

In the late 90s, while studying education at the University of Illinois at Chicago, Vasquez became a member of Molemen himself. Through a rapper he knew in New York, he landed a spot on MTV’s hip-hop countdown Direct Effect. “Then I ended up being part of the HBO Blaze Battle, which was the first televised MC battle—most of the city then was like, ‘Oh, you’re the guy,'” Vasquez says. “It went from not having a community to, like, ‘Here’s your community, here’s what we do all the time, here’s everyone to connect with,’ and really feeling valued for myself. I’d never pictured I’d have anything like that, so when I did I was full in.”

Chicago rapper Pugs Atomz, then head of the Nacrobats crew, befriended Vasquez through battling. Atomz saw Vasquez’s leadership qualities and drive back then, and describes him as “tenacious and not accepting ‘no,’ and willing to create the things we wanted to see. Like, ‘All right, let’s go to New York tomorrow.’ ‘Let’s go battle at Scribble Jam.’ That’s what we’re doing. We were just always both ready to do it, and willing to take the lead if necessary—and support each other.”

Vasquez provided the Molemen with infrastructure and promotional support. He’d sell Molemen tapes at Navy Pier and the Taste of Chicago and wear Molemen T-shirts while working at Gramaphone Records. When the Molemen were working on their expansive 2001 double album, Ritual of the . . . , Vasquez helped bring in rappers from outside the crew. “I was going back and forth to New York, so I actually hooked up a lot of those songs as an executive producer,” he says. “Some of the songs that were there, it was definitely me putting that together—I was just super geeked to be a part of it all.” Ritual features Chicago greats such as E.C. Illa, Rubberoom, Juice, and Rhymefest, plus out-of-town heavies such as Aesop Rock, MF Doom, and Atmosphere rapper Slug. Vasquez got the track “Unbreakable” to himself, though it’s his only appearance.

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.”

Vasquez had already formed another crew, Middle Ground, in 2001, and there he was more a mentor than a peer to the other rappers. “I just wanted to see what it’d be like to actually start my own group of folks, and little-bro with some other folks who were rappers,” he says. Robles remembers the advice he gave Vasquez as he left the Molemen: “I told him, ‘If you start your crew, you’re still going to have to clean toilets,'” he says. “But the person that cleans the toilets cares about the crew.”

Middle Ground released a couple albums in the late 2000s, but like most of Vasquez’s recorded output, they’re hard to find these days. Aside from the stray YouTube upload—the title track to Madman, for one—Vasquez’s music isn’t streamable. And he’d prefer to keep it that way. He’s unhappy with the sound quality of many of the recordings, and with some of the things he was saying in those songs.

“The part that’s really problematic about hip-hop music is that it’s plagued by toxic masculinity, misogyny, homophobia—and if you’re a battle rapper, that’s your world,” he says. “There’s a lot of things I’ve said in the past that I am incredibly sorry for, thinking about what folks who have lived different experiences feel when they hear it. I think, as a person of color, when you listen to hip-hop music, you’re like, ‘Yes, it’s a strong voice from a black or brown person, and I need that in my life ’cause I never had those role models.’ But it’s hard then to separate it and go, ‘Yeah, that’s great, but you’re also offending and putting other people down because of it.’ There’s definitely a lot of records where I’ve said stuff that was of that vein.”

Vasquez acknowledges this in a voice-over in the video on the front page of his campaign website: “Being a hip-hop artist taught me to develop my voice, when as a person of color I didn’t think that I had one. I’m not always proud of how I used my voice in the past, but it’s where I started and where I moved from.” The video shows glimpses of Subterranean, where Vasquez spent many Tuesday nights at the long-running open-mike series. “I’d battle like five, six people at once onstage,” he says. “I definitely had a reputation for wanting to battle. People would throw drinks to try to throw me off—this was not a friendly, conducive environment. But it’s definitely what it was, and it was entertainment.”

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.”

In the early 2010s, when Vasquez was running that AT&T store, he decided to leave music. In 2013, he enrolled in Kaplan University (now Purdue University Global), where he earned an associate’s degree in business administration a year later. Since 2011 he’s been a marketing accounts manager for AT&T, overseeing the accounts of around 11,000 apartments and condos throughout Illinois; he continues to juggle the job with his campaigning.

When Vasquez took an interest in Bernie’s presidential campaign, he shared his enthusiasm through some of the same channels he’d used to share music. “Facebook, Twitter, Instagram: the same way I would promote songs, videos, albums back in the day. It remained the way I stayed connected to people,” he says. “Folks would be like, ‘Oh, I didn’t even know this guy was running—I had no idea.’ It felt really cool to be able to plug people in who weren’t a part of the political process at all, and just connected with me from a different history that we share.”

When he organized Bern Fest in March 2016, he called on old friends from his life in hip-hop. Veteran battle rapper Shadow Master and a duo of Pugs Atomz and rapper-producer Awdazcate took the stage among speakers such as Black Lives Matter activist Ja’mal Green, My Block My Hood My City founder Jahmal Cole, Cook County State’s Attorney candidate Kim Foxx, and 2015 40th Ward aldermanic challenger Dianne Daleiden.

Bern Fest impressed at least one of the community organizers in attendance. “One of them stayed around at the end and was like, ‘What are you doing next?’ And I was like, ‘I just know how to throw shows,'” Vasquez says. “They were like, ‘You should come to one of our trainings, because you’ve been community organizing.’ That’s what led me to do the canvass.”

That organizer was Amanda Weaver, executive director of Reclaim Chicago, and Vasquez joined her organization to run chapter meetings in his ward and launch a monthly series encouraging informal conversations about politics at neighborhood bars—he called it “Drinks and Discourse.” (“I like alliteration, ’cause I’m a rapper,” he says.) And just as people used to come out to his shows, they came out to his events. “That’s where I started seeing it and going, ‘Oh, we’re getting a turnout of 80 to 100 people—how can we turn that into power?'” Vasquez says. “I became the chair of the Reclaim Chicago North Chapter—it was so focused on the 40th Ward. I was already having the idea, like, ‘Maybe this is a thing.'”

Che “Rhymefest” Smith and Andre “Prime” Vasquez at Metro in 2007 for the Molemen’s Chicago Rocks festivalCredit: Courtesy of Andre Vasquez

Reclaim Chicago spokesperson Kristi Sanford remembers Vasquez from Bern Fest and considers him an embodiment of the organization’s goals. “This is what we’re all about—regular people running,” she says. She sees Vasquez’s unconventional trajectory and his hip-hop past as assets. “What Andre’s doing is showing by taking this risk that all of us can do politics, and it’s going to take all of us doing it to change the city,” she says. “It’s inspiration to the rest of us who were always told, ‘This is not your place.'”

Sanford says Vasquez is already doing some of the work he’d need to do to in order to accomplish things in City Hall. “I know Andre’s building relationships with all the other candidates we’ve endorsed,” she says. “We could see a new class of freshman aldermen with relationships with each other and fresh vision for the city.” Ramirez-Rosa is the lone incumbent of the five candidates with Reclaim endorsements—the others are Colin Bird-Martinez (31st Ward), Rossana Rodriguez (33rd Ward), and Maria Hadden (49th Ward).

Running a competitive race against Chicago’s second-longest-serving alderman requires plenty of cash. And challengers who rely largely on small individual donations are at a huge disadvantage against incumbents such as O’Connor, who have establishment money from industry groups, PACs, and unions. According to data provided by the Illinois State Board of Elections, Vasquez has a little more than $20,000 cash on hand. Daleiden and O’Keefe trail him closely, with around $16,000 apiece, and Okere is in a distant last place with about $6,000. But O’Connor’s budget dwarfs those of all four challengers combined: the Citizens for Patrick O’Connor committee has nearly a quarter million dollars.

Vasquez is nonetheless confident he can force O’Connor into a runoff. “We’ve raised the most money out of all the challengers; we’ve gotten the most petition signatures,” he says. He estimates he has more than 200 volunteers helping him knock on doors and make calls. “I love actually knocking and hearing the stories from everybody,” Vasquez says. “You learn so much and you see so much of your experience in someone else’s.”

The capstone of Vasquez’s hip-hop career, as he tells it, was a studio session with New York rapper KRS-One in 2008 (they released a song with Que Billah called “Todays Lesson”). In some ways that collaboration prefigured his interest in community organizing and public service—KRS-One has been one of the most prominent political voices in rap for more than 30 years. “I had learned so much about society and about politics without even knowing about it, listening to KRS,” he says. “It was really full circle for me, and I was able to go, ‘I’ve accomplished more than I expected, we’re good.'”

Though Vasquez has left rap behind, the friends he made during that chapter in his life first helped him understand what it meant to be part of a community—and he wants to hang on to that feeling. When Vasquez started fund-raising for his campaign last year, he called up some of his old comrades to help. Che “Rhymefest” Smith headlined a show in August called “Chicago Hip Hop for Prime.” Sean Daley, aka Slug from Atmosphere, donated $1,500, and Atomz and Robles gave money too. Vasquez understands that as an activist and aldermanic candidate, he has the opportunity to do for others what the rap scene did for him—to connect them to something bigger and more powerful than themselves. “He wrote me this card from his campaign, ’cause I donated,” Robles says. “He personally wrote on the back, saying I was the closest thing he ever had to a big brother.”  v