Bobby decided then to take rapping and his music career seriously: “I didn’t really care too much for it until I went to jail and I seen how the fans were loyal,” he tells me. “I can’t name a week that I didn’t see at least 10 [pieces] of fan mail, throughout the whole bid.” Which begs the question: If that epiphany happened in 2016, then what was on his mind the summer that he had a Top 10 Billboard single and a seven-figure label deal? “Money and bitches, I ain’t gonna lie to you,” he says. “I was 19 turning 20, coming out of the [East Flatbush] ’90s, one of the worst neighborhoods in Brooklyn.”
While we’re talking, Bobby pauses to take a FaceTime call from Meek Mill, and the two commiserate over the unfamiliar emotion that Bobby experienced after reading this letter: shame. “Hell, yeah,” Meek empathizes over the phone, “I was embarrassed every time.” “I’m done with that [jail] shit,” Bobby vows to Meek, cracking, “I’ll be light-skinned in Jamaica before I go back.” Meek, who has experienced reintegrating into celebrity life after jail a couple of times now, warns Bobby that the next three days are going to feel fast and disorienting.
“I left my godkids. They were four or five when I used to take them all to the store,” Bobby tells me after hanging up with Meek. “Now it’s been seven years. I used to lie to them, say I was on tour, but kids are smart. I missed out. Even that little half decade of their lives, that’s important to me.”
Going to prison immediately after blowing up made Bobby appreciate just how fortunate he was to have achieved rap stardom—and understand that it was almost taken from him before he had the chance to fully realize it. Though he refers to 2014 as a “love/hate year,” he acknowledges how the work he put in then set him up to come home to endless opportunities. “Otherwise, by now I’d probably already have a gun and some crack,” he tells me. “The streets are talented. I saw that shit in jail, all day. There’s basketball players, smart-ass motherfuckers, niggas who know this or that but just don’t know how to apply their shit, or have behavior problems. But niggas not taught to apply their shit where we come from.”
The precise date of Bobby’s parole wasn’t finalized until January. But according to Quavo, plans for his first day out began six months to a year ago, on one of their many phone calls. “He had this dream: a jet, flooded out with his gang, his family, a couple vibes [read: women] for him.” The rapper, who helped pay for the day’s festivities, is drowsy from pulling an all-nighter to make sure his friend’s morning went exactly how he imagined. But he’s ready to rally at a moment’s notice: “It’s like his birthday today. Whatever he wants to do, we’re doing it.”