Tupac Shakur (left) met Leila Steinberg when he was a 17-year-old senior at Tamalpais High School in Mill Valley. She managed him from 1989 to 1993. (Photo/Kathy Crawford)
Tupac Shakur (left) met Leila Steinberg when he was a 17-year-old senior at Tamalpais High School in Mill Valley. She managed him from 1989 to 1993. (Photo/Kathy Crawford)

‘Dear Mama’: Leila Steinberg, Tupac’s first manager, sees new docuseries as a chance to heal

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In 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 by phone in a rare interview, her first with a Jewish media outlet. “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 would go on to become Tupac Shakur’s first manager, helping to launch the career of arguably the most influential — and most controversial — rapper ever. She also served as a substitute mother to him at a time when his own mother was struggling with drug addiction. He would leave his Marin City home and crash on Steinberg’s couch for a while.

In the new docuseries “Dear Mama,” Steinberg and other friends, relatives and associates of Shakur’s reflect on his unique life and impact. The five-part series, directed by Allen Hughes and currently airing on FX (with all episodes available to stream May 13 on Hulu), interweaves Shakur’s story — he started out as a dancer with Oakland-based rap group Digital Underground, then achieved enormous success as a solo rapper and actor before being murdered at age 25 — with the lesser-known story of his activist mother Afeni, a member of the Black Panther Party in New York City.

The April 21 premiere was FX’s most-watched premiere of an unscripted series, a testament to the public’s enduring fascination with the entertainer, who died in 1996 and was once described by the Los Angeles Times as “a ghetto poet whose tales of urban alienation captivated young people of all races and backgrounds.”

Steinberg told J. she has always felt uncomfortable talking to the press and reluctantly agreed to appear in the docuseries after Hughes, who directed a few of Shakur’s early music videos, won her over.

“I want to see us learn something” from the series, she said. “I want us to grow and do some healing.”

She added that she has wrestled with feelings of guilt for years — both over the privilege she enjoyed as a white Jew working in the entertainment industry, and over the “toxic” quality of some of the music Shakur released and the poor decisions he made that led 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.”

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. 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 an Ashkenazi father who worked as a criminal defense lawyer and a Sephardic, Mexican-born mother who was involved in different social movements, Steinberg attended a predominantly Black and Latino elementary school in L.A. When she was in sixth grade, her family moved to a “pretty Waspy” community in Santa Monica. As a result, she did not have many Jewish friends growing up, she said. (Her brother had a bar mitzvah, but she did not have a bat mitzvah. Today she is not actively involved in the L.A. Jewish community.)

Steinberg said she first became aware of the power of music sitting in the pews of a Sephardic synagogue on Wilshire Boulevard. “When Cantor Behar sang, I felt like that was the deepest connection to God,” she said, referring to Cantor Isaac Behar of Sephardic Temple Tifereth Israel.

She sang in youth choirs and took 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. For a few years she toured with the band O.J. Ekemode and the Nigerian Allstars; she was the only non-Black singer-dancer in the Afrobeat group. It was on the group’s first U.S. tour that she realized she could have a greater impact in the music world by helping artists of color get more exposure. So she started promoting shows around the Bay Area and contributing to the growing hip-hop scene.

“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.”

The first episode of “Dear Mama” includes a clip from a 1995 deposition that Shakur gave in which he 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. “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.”

Ray Luv, a Santa Rosa-raised rapper who met Steinberg when he was 15, 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 in an interview.

Luv participated in her 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 managed Shakur from 1989 until 1993 (with guidance from Digital Underground’s manager, Atron Gregory), approaching the job as if she were Shakur’s campaign manager. In one eyebrow-raising statement, she says in the docuseries, “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 told J. “He felt through his lyrics and songs he could be a roadmap to empathy and change and transformation.”

Although they came from very different worlds, Steinberg and Shakur bonded over their shared commitment to racial justice.

Steinberg continues to give workshops on emotional literacy at schools and elsewhere through her nonprofit, Aim4theHeart. (Photo/Louis King)
Through her nonprofit, Aim4thHeart, Steinberg gives workshops for young people on emotional literacy. (Photo/Louis King)

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. “There were times I felt when I got married I would change my 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 she lives in Santa Rosa, and mother and daughter have a close relationship, Steinberg said.

Asked about her relationship with Afeni, Shakur’s mother, Steinberg replied, “We had a complicated relationship because 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. It was always awkward, but I know she loved me and my kids, and I have immense respect and love for her.” (Afeni lived in Sausalito in her later years and died in 2016.)

“Dear Mama” takes its title from one of Shakur’s best-known songs, a loving tribute to his mother on his 1995 album “Me Against the World.” She 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. Afeni 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.

“And even as a crack fiend, Mama, you always was a Black queen, Mama,” Shakur raps on “Dear Mama.” “I finally understand, for a woman it ain’t easy tryin’ to raise a man.”

While he could be very charismatic, as those who knew him attest in the docuseries, he also had his demons. In a TV interview that opens “Dear Mama,” he compares himself to the beleaguered Job of the Bible.

His many tribulations included being beaten by Oakland police officers after they stopped him for jaywalking in October 1991 (he sued the police department and received a settlement); getting into a fight at the 1992 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); assaulting Allen Hughes after the director fired him from his 1993 movie “Menace II Society” (an incident Hughes addresses head-on in “Dear Mama”); and getting shot five times at a New York City recording studio in 1995 while on trial for sexually assaulting a female fan in a hotel room two years earlier (he and his road manager were convicted; Shakur served nine months in jail).

“I don’t want people to think I condone all his behavior,” Steinberg said. “I fought with him all the time.” (She doesn’t believe he assaulted the woman in the hotel but said that he was responsible for controlling 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, including Judaism and the Israeli-Palestinian conflict. “He was definitely pro-Palestinian, and he believed they were there first,” she said. “He challenged me, as a Jewish person, to be educated enough to take a position that there needed to be a solution that did not remove Palestinians from their land.”

After Shakur was shot in a drive-by shooting in Las Vegas in 1996, Steinberg said she was convinced he would pull through.

“I was in shock for a very long time” after he died several days later in a hospital, 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 L.A. 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 through her nonprofit Aim4theHeart and which are designed to promote emotional literacy.

For three decades, she worked with prisoners at San Quentin State Prison, but 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 son who is a musician 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.’”

Andrew Esensten
Andrew Esensten

Andrew Esensten is the culture editor of J. Previously, he was a staff writer for the English-language edition of Haaretz based in Tel Aviv. Follow him on Twitter @esensten.