Chicago rapper Myquale’s Red Bull Setlist win came with a personal moment he wanted to share: telling his younger brother, who is incarcerated, that he had won the competition.
In an Instagram post, Myquale shared a clip centered on the conversation. Its caption read, “POV – Telling my incarcerated brother I won the competition. See yall October 24th.” The news means Myquale will open for Lil Yachty at Red Bull Setlist at Radius Chicago this Saturday.
The moment connects to what Myquale has shared about the brothers’ relationship. In a separate post promoting his song “TIME #OFF #FREEBRO,” he wrote that he rarely shares his personal life online. He described helping pay attorney fees for his younger brother years ago, and the strain of seeing someone he grew up close with incarcerated. “We shared rooms. Now it’s visitations. Phone calls. Commissary,” he wrote, closing with, “Free bro til it’s backwards.”
That bond also runs through music. Myquale said hip-hop has long been a shared language for the brothers, who grew up around family ciphers. Red Bull’s profile of Myquale describes him sharing the competition news with his brother by phone, where the conversation turned into a back-and-forth freestyle.
Myquale earned the opening slot after advancing from the Red Bull Setlist Rap Booth competition’s final three. Fans voted among Myquale, June and Mike DFG after Lil Yachty and Lyrical Lemonade selected the finalists. Myquale told Red Bull that he actively encouraged people to vote for him.
The Chicago-based rapper, who was raised in Milwaukee and moved to Chicago in 2014, began making music at 14, according to Red Bull. His win now brings that journey to a major Chicago stage—and gives him a chance to celebrate the moment with the person he wanted to tell first.
Red Bull Setlist takes place at Radius Chicago on October 24. Myquale is scheduled to open for Lil Yachty.
