[4][1] 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 underground hip-hop collective Molemen.

[4] 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.

[1] 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.

[10] 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.

[7] 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 78 real estate developments.

[12] 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.