During the late 1990s and early 2000s, Vasquez performed as a hip-hop artist under the stage name Prime, a reference to the fictional characterOptimus Prime. He first became involved in battle rap during his time at Lane Tech High School in the early 1990s, and later became a member of the undergroundhip-hop collective Molemen. He also toured with the hip-hop group Atmosphere and appeared on MTV's Direct Effect and HBO's Blaze Battle. He ended his career as a rapper in 2010. Vasquez's career as a rapper later became the subject of controversy during his 2019 campaign for Chicago City Council, when his opponent criticized him for using misogynistic and homophobic lyrics. Vasquez apologized for the lyrics, saying that "As a person who felt inadequate in my own skin, I thought denigrating others would make me feel bigger and there is no excuse for that."
Early political career
Vasquez became involved in electoral politics during the 2016 presidential election as a supporter of Bernie Sanders. As of 2019, he was the chair of the north side chapter of Reclaim Chicago, a progressive political action committee. In May 2018, Vasquez officially kicked off his campaign for alderman of Chicago's 40th ward. He was one of five candidates who appeared on the ballot in the first-round election on February 26, 2019, where he placed second with about 20 of the vote. Since no candidate received more than half of the vote, he and 36-year incumbent Patrick J. O'Connor advanced to a run-off election held on April 2. Vasquez defeated O'Connor in that election, receiving 54% of the vote. On April 10, 2019, Vasquez joined six other newly-elected members of the City Council in protesting against the approval of tax increment financing for the Lincoln Yards and The 78real estate developments.
Chicago City Council (2019–present)
Vasquez was sworn in as a member of Chicago City Council on May 20, 2019. In November 2019, Vasquez was one of eleven aldermen to vote against Mayor Lori Lightfoot's first budget. He joined all five other members of the Socialist Caucus in signing a letter to Lightfoot which criticized her budget for "an over-reliance on property taxes" and "regressive funding models" that are "burdensome to our working-class citizens, while giving the wealthy and large corporations a pass."