n the late 1980s, Leila Steinberg was a concert promoter and arts educator living in Rohnert Park. Each week, she hosted writing circles for young poets, rappers and actors in her living room. She would give the participants a prompt, and then invite the best ones to perform their pieces during assemblies at schools across the Bay Area.
One evening in 1988, a senior at Tamalpais High School in Mill Valley showed up and challenged Steinberg’s approach, telling her the participants should have more input on the content of the assemblies. That brash 17-year-old would have a profound impact on Steinberg’s life, and on the lives of so many others around the world.
“It was my group until Tupac came,” Steinberg recalled in a recent phone interview. “I was in my 20s, and it was just a passion project that I wanted to do. His joining really allowed me to rethink and reshape what it was to be in a leadership role.”
Steinberg was part of a multicultural community of mentors and friends who helped mold Tupac Shakur, both as an artist and a man, during the years he lived in Northern California. After making his commercial recording debut with Oakland-based rap group Digital Underground, Shakur achieved enormous success as a solo rapper and actor before being murdered in 1996 at age 25.
In addition to promoting his first shows, Steinberg was Shakur’s first manager, as well as a substitute mother of sorts to him at a time when his own mother, Afeni, was struggling with drug addiction. He would eventually leave his Marin City home and crash on Steinberg’s couch, living with her and her family in Rohnert Park.
For years, Steinberg wrestled with feelings of guilt over the “toxic” quality of some of the later music Shakur released, and the poor decisions he made that may have contributed to his untimely death.
“Tupac was a kid, and he needed a lot more guidance,” she said. “I was too young to understand what I know now. I wish that I could have had more influence, because I always stayed connected to him.”
Finding her role in hip-hop
Steinberg, 61, lived and worked in the Bay Area for about 15 years in the 1980s and ’90s. Today she lives in Los Angeles, where she grew up, though she returns periodically to visit her mother in Santa Rosa. “The Bay is one of the most revolutionary areas you can live in, in this entire country, whether it’s education, politics, religion,” she said.
In addition to managing Shakur from 1989 until 1993 (with guidance from Digital Underground’s manager, Atron Gregory), Steinberg managed Ray Luv and Mac Mall, and she remains close to both of them. She still manages artists, including the rapper Earl Sweatshirt, through her company Steinberg Management International. It’s a career she fell into by accident. “I was horrible at math and business, so it’s weird that I ended up negotiating million-dollar contracts,” she said.
The daughter of a white, Jewish father who worked as a criminal defense lawyer and a Mexican-born mother with Sephardic Jewish heritage who was involved in different social movements, Steinberg first became aware of the power of music while sitting in the pews of a synagogue. “When Cantor Behar sang, I felt like that was the deepest connection to God,” she said, referring to Cantor Isaac Behar of L.A.’s Sephardic Temple Tifereth Israel.
She attended a predominantly Black and Latino elementary school in L.A. until sixth grade, when her family moved to a “pretty WASP-y” community in Santa Monica, she said. She gravitated to the arts, singing in youth choirs and taking African dance classes at a cultural center. “I began to learn about African culture and the gift that came from Africa that I didn’t have in my family, in my community,” she said during a 2021 forum at UC Berkeley.
Although she studied sports therapy at Sonoma State University and worked at a physical therapy office in Sebastopol, she always thought of herself as an artist. She toured with the band O.J. Ekemode and the Nigerian Allstars for a few years, the only non-Black singer-dancer in the Afrobeat group. On the group’s first U.S. tour, she realized she could have a greater impact in music by helping artists of color get more exposure, so she started organizing shows around the Bay Area and, with her DJ husband, promoting local hip-hop acts.
“I never planned on being in hip-hop or rap music,” she said at UC Berkeley. “I really understood the eruption of pain, and that this art form was a very important conversation.” However, she added, “I also struggled with what my role would be.”
In Dear Mama, a 2023 FX docuseries (now streaming on Hulu) that interweaves Shakur’s story with his activist mother’s, Shakur talks about Steinberg’s influence on him.
“She was older, she was white, and she’s the one that I used to let look at my poetry,” he says in a clip from a 1995 deposition. “She understood a lot of things that I was doing that other people couldn’t understand. And she’s the one that stayed on me about working hard to do my music.”
‘She required us to be honest’
Ray Luv met Steinberg when he was 15, and in an interview, he described her as an educator at heart. “She wants people to be aware of what’s going on, and to not just be blowing in the wind, but to have a voice and to use it,” he said.
Luv grew up in Santa Rosa, participated in Steinberg’s poetry circles in the late 1980s, and performed with Shakur as a member of the rap group Strictly Dope from 1988 to 1990. He recalled how Steinberg drove them back and forth between the North Bay and recording studios in the East Bay, even when she was several months pregnant.
“It had to put an incredible strain on her family,” he said of her commitment to him and his peers. “She was also feeding some of us and putting us up at different times when we didn’t have a place to stay. I’ve seen her acts of kindness.”
In return, he added, “She required us to be honest. She required us to give back to the community.”
Steinberg approached the job of managing Shakur as if she were running a political campaign, drawing upon lessons she learned from an uncle who worked in politics in L.A. “I instinctively began to look at throwing parties and events and shows like a political campaign, and I understood music moves masses,” she said.
Yet Shakur did not see himself as a politician. Instead, as Steinberg says in Dear Mama, “Tupac wanted to seduce the children of white America.”
What did she mean by that? “He really wanted to be like the Pied Piper, and he wanted to lure a generation of white children who grew up not understanding struggle or justice, or what’s happened to Black people in this country,” she said in the interview. “He felt through his lyrics and songs he could be a roadmap to empathy and change and transformation.”
Ain’t a woman alive that could take my mama’s place
The documentary Dear Mama takes its title from one of Shakur’s best-known songs, a loving tribute to his mother included on his 1995 album Me Against the World.
Afeni Shakur was one of the Panther 21, a group of Black Panthers arrested in New York City in 1969 and charged with conspiring to bomb department stores and police stations. She was pregnant with Shakur while in jail, and defended herself at trial, despite having no legal training. She and the other defendants were acquitted in 1971, and she raised Shakur and his half-sister in poverty in Harlem, Baltimore and Marin City.
Although they came from very different worlds, Steinberg and Shakur bonded over their shared commitment to racial justice.
As the Jewish daughter of a dark-skinned Mexican immigrant, Steinberg said she was aware of antisemitism and racism from a young age. “I understood that Jews were not liked, but they could disappear in their Jewishness,” she said. When she got married, she considered changing her last name, “but I felt that I needed to be OK and not hide, because Black people couldn’t hide their skin.”
Another thing she had in common with Shakur, she said, was “mother issues.”
“We shared a pain of having mothers who came out of ’60s activism and were taken away from their children because of their choices at times,” she said. “The ’60s activism included drugs, sexual behavior and a lifestyle that is really not healthy for a family.” Steinberg’s mother, Corina Abouaf, was involved in the farmworkers’ and women’s movements. Today, mother and daughter are close, Steinberg said.
As for her relationship with Afeni, Shakur’s mother, who lived in Sausalito in her later years and died in 2016, Steinberg says it was complicated.
“I don’t think that I would have been as involved in pushing Pac’s career forward, and just being there for him, if she wasn’t in the place she was in,” she said. “But I know she loved me and my kids, and I have immense respect and love for her.”
‘I still feel his partnership’
Tupac Shakur’s time in the Bay Area was often turbulent. In October 1991, he was beaten by Oakland police officers after they stopped him for jaywalking; he subsequently sued the police department and received a settlement. The following year, he was involved in a fight at the Marin City Festival, during which a 6-year-old boy was killed by a bullet fired from a gun that was registered to Shakur. (He was never charged with a crime.)
“I don’t want people to think I condone all his behavior,” Steinberg said. “I fought with him all the time.”
Steinberg doesn’t believe he sexually assaulted a female fan in a New York City hotel room, a crime he was convicted of in 1995, and for which he served nine months in jail. His road manager was also convicted of assaulting the woman, and Steinberg said Shakur should have had better control over the members of his entourage.
She has said she fell in love with Shakur in a spiritual sense, and the two of them talked about everything. After Shakur was shot in a drive-by shooting in Las Vegas in 1996, Steinberg said she was convinced he would pull through.
After he died several days later in a hospital, “I was in shock for a very long time,” she recalled. “I’ve been operating for so long from so much trauma, and I’m finally in a really healthy place.” (His murder has never been solved, but in 2002 the Los Angeles Times identified a since-deceased gang member from Compton as the probable shooter.)
Steinberg saved many of the poems Shakur wrote between the ages of 17 and 19 and published them, with his prior permission, in the 1999 book The Rose That Grew From Concrete. Her portion of the sales has helped to fund her “Mic Sessions” workshops, which she offers at school, universities and other venues through her nonprofit Aim4theHeart, and which are designed to promote emotional literacy.
For three decades, she worked with prisoners at San Quentin State Prison, until the pandemic forced her to press pause. She is a self-described nomad who often travels with Earl Sweatshirt, explaining that the 29-year-old rapper has allowed her to redeem herself “after all the mistakes with Tupac.” She is the mother of four adult children, including a musician son known as Nyku, and a grandmother. She is writing a memoir.
Even today, she said, Shakur is still very much a part of her life.
“I thought he would be alive doing the work with me,” she said. “I still feel his partnership in the work. I still feel him tapping me on the shoulder and saying, ‘You have a responsibility. Keep going.’”