His second love was gangster film and television—Goodfellas and Scarface, The Sopranos and The Wire—and after short-lived attempts at rapping and making music videos, he found a way to combine his passion for hip-hop with the larger-than-life stories so often lurking behind the genre’s biggest names. In 2019, his YouTube video “Why Jay-Z Shot His Brother At Age 12” gave him his first taste of virality and set him on his current path as a journalist.

Ross found the lives of Chicago rappers such as Durk and Von equally compelling, and his coverage of the city’s gang culture became his calling card. As the Durk proceedings unfolded, his relentless output made him something like the Dominick Dunne of what fellow rap media personality Adam22 describes to me as “arguably the biggest hip-hop trial ever.” (The New York Times’ Jon Caramanica, in turn, once described Adam’s media platform No Jumper as “The Paris Review of the face-tattoo set.”)

“I don’t think you can think of anyone as a reporter who’s ever done anything even close in terms of just really owning and controlling the narrative,” Adam says of Ross, “and just day in, day out, really demonstrating to everybody like, Oh, if you wanted to actually maximize your coverage of this event, this is what it would look like.”

Ross attributed the intensity of the reaction he’s faced to the depth of Durk’s fandom—he has a Von tattoo himself, and he says he could understand where the defendant’s supporters were coming from. “He’s one of, if not the best Chicago drill rapper to ever do it,” Ross says, referring to the local hip-hop subgenre that Durk helped popularize on a national stage in the 2010s. “But unfortunately I think the quality of his music and his persona maybe blinded some people to the reality of the situation,” he continued, emphasizing that the case dealt with the killing of a 24-year-old man, Saviay’a Robinson, whose mother attended some of the proceedings. “If Durk’s found not guilty, I absolutely respect that,” Ross said before the verdict had been announced. “But I do feel like there’s real pain in that courtroom from the victim’s side and their family. And I think it is really sad when people act like there was no victim.”

As the trial wore on, Ross sparred with Durk’s publicist Holly Baird, whose clients have also included Sean “Diddy” Combs, on X after he highlighted ostensibly negative developments for Durk—testimony or evidence that he’s excitedly described as instances of the government having “cooked” the rapper. According to Ross, Baird screamed at him to delete one of his tweets “to the point where the court marshals had to involve themselves and basically separate her from me and tell her to calm down.” (“It would be beneficial for him if I was the irrational woman he claims me to be,” Baird tells me, noting that Ross deleted the “untruthful” tweet in question and that she is on friendly terms with Ross’s security guards and the court marshals. “I’m not the big bad Black wolf he wants to paint me as.” Through an assistant, Ross said that he “dealt with the exchange on its individual merits and described the interaction as he experienced it … and would never treat or speak about someone differently because of their race or religion.” After Baird told Ross that I’d reached out to her, he also provided, without my asking, a 12-page document offering his version of the social media dispute, titled “Ross x Holly Beef Timeline,” which acknowledged that he had made a transcription error but said he corrected it before Baird’s intervention.)