The result was the trip to Samoa, to a location chosen by Thebe's mom, Steinberg said, because she "wanted him to have a habilitation experience that was unlike any other, which I think was amazing."
His absence, though, prompted members of Odd Future and fans to launch a "Free Earl" campaign, incorrectly implicating an uptight mom standing in the way of destiny. Online diggers found a photo that confirmed that he was in a Samoan juvenile rehabilitation facility, where he could legally be held until age 21.
While there, Odd Future's music gathered media attention, positive and negative. Amid the punk-suggestive shock, playfulness, a love of button-pushing language and sinister, minimal beats, members joked about rape and tossed around immature homophobic insults while showcasing a keen understanding of social media and self-promotion.
Despite the criticism, Thebe's renown expanded into the literary establishment when he was profiled in 2011 by the New Yorker, a peak for artists of any age. The 8,000-word story reported not only on his situation but identified his mother as a teacher (later reported to be respected civil rights attorney and UCLA professor Cheryl Harris) and his father, Keorapetse Kgositsile, as the lauded South African poet and activist for the African National Congress as it pushed toward reform in the apartheid-era country.
The son had scored hip-hop, literary and genetic cred before he'd even issued a proper debut album. To add to the mystique, noted the New Yorker's Kelefa Sanneh, one of the father's most important poems had prompted an influential New York proto-rap group to name themselves the Last Poets.
That was long before Earl Sweatshirt was born, and the genre the Last Poets and Gil Scott-Heron inspired is now more than three decades old.
Asked about the state of hip-hop, though, the young artist was blunt: "I think rap is either on the cusp of dying or having a renaissance. It's one of the two. You can hit your head against the same wall a bunch of times, especially now." He referred to the genre as "a dusty-ass bucket."
He became a lightning rod a few weeks ago when he dismissed Jay Z's new album, "Magna Carta Holy Grail," in a simple (cussed) tweet: "If you really [messed] with Magna Carta then unfollow me." The tweet prompted much backlash and a few more tweets from Earl, including: "I hope that opinions on my material throughout my career are based on the quality of it and not how big my name is."
To say Thebe was overwhelmed by the attention upon returning is an understatement, he said, easing into conversational mode while trying to sketch out the Tan Cressida logo, the piano loop echoing behind him. The pressure to dive into the chaos of an Odd Future tour was heavy. "It was like, get on the stage and everybody has these huge expectations. 'Oh, my God, the prodigal son!'"
He paused, then added: "And I have my own self-esteem issues, so [stuff] like that doesn't get to me. It actually just makes me question people's agendas and tastes."
While he was away, Harris was searching for a business advisor with integrity, one whose agenda would help guide her son through the tangles of the music business.
"Thebe and I had been talking quite a bit about his music and his desire to build a career when he got back," said Harris. She and administrators and board members at New Roads brainstormed, and Steinberg's name came up as someone "who would understand that it's Thebe's well-being and not just his career. It's about Thebe as a human being and not just Earl as a commodity."
So Harris reached out to Steinberg, who, after Shakur's death, had quit what she described as a "toxic and painful" music business. "I lost so many people that I love."
Steinberg founded an L.A.-based nonprofit called Alternative Intervention Models, which helps needy kids find artistic outlets and offers regular workshops at San Quentin penitentiary. Still, she continued to contemplate a return to management. "I felt like I'd learned so much, but I felt like I needed the right time to come back in and do something."
That moment occurred just after Thebe was sent to Samoa. Coincidentally, the week before she was contacted, Steinberg had focused a lecture to USC law students on the ways in which music drives culture and art — and the focus was the "Earl" song and video.
For his part, half a world away Thebe had just finished the only hip-hop book in the library: "Holler If You Hear Me," the Michael Eric Dyson biography of Shakur that detailed Steinberg's role in his ascent.
They began phone and Skype conversations, and it seemed a natural fit. "I fell in love with him just as this young, brilliant kid who has an artist and activist and an attorney sitting on his head," said Steinberg.