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Culture & Conversation Family

In Tupac’s ‘Dear Mama,’ a Backstory About His Mother’s Activism, Mass Incarceration, and Bail

Brandi Collins-Calhoun

This Mother's Day, I'm listening to the song as a tribute to Afeni Shakur, but also to families separated by mass incarceration.

It’s not really Mother’s Day until I find myself ugly-crying and reciting the lyrics to Tupac’s anthem “Dear Mama.” This has been the routine ever since I was a little girl in the ’90s, because it seemed the song that best described what it was like to love and appreciate our Black mothers and caregivers.

But recently, my relationship with the song has changed because I’ve changed. I’ve made the transition from being a Black daughter to being a Black mother myself, and trying to abolish the bail system made me pay more attention to the history behind the song.

Now, after listening to this song a thousand times, I realize—and this may sound obvious—this song is mostly from Tupac’s perspective even while it’s a family story. It illustrates the experiences of children whose mothers struggled to sustain households on their own due to their “shortcomings” and absent fathers. It’s also the relatable story of a mother-son relationship’s ups and downs: He talks about her as both “crack fiend” and “Black queen,” of both blaming her and admiring her because “for a woman, it ain’t easy trying to raise a man.”

But these words, no matter how they were intended to show a complex relationship, are still from a child’s perspective. And it’s often hard for children to understand their parent’s lives in totality and not in relationship to them.

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For all “Dear Mama” is a love letter to the late Afeni Shakur, but it took me a while to hear this lyric: “It was hell hugging on my mama from a jail cell.” This Mother’s Day, as I’m working as part of a team to raise money to bail Black mothers and caregivers out from jail, the song’s lyrics made me think about Afeni Shakur as more than a woman who had a drug problem and a sometimes-difficult relationship with her famous son.

I initially understood the lyrics as Tupac’s simply loving his mom through the hard times. What I didn’t really hear was Afeni’s incarceration in New York’s infamous Rikers Island jail complex; how jails separate families; and how she was an activist-ancestor of mine, trying to up-end the cash bail system.

I didn’t realize that the hard times started in 1969 when Afeni was arrested, along with other members of the Black Panther Party in New York City (known as the Panther 21), for allegedly conspiring to bomb a number of police stations and department stores.  Their bail was set at $100,000, a ridiculously high amount.

The Black Panther Party and its community organized efforts to raise funds. However, Afeni was known among her Black Panther comrades for raising bail money for fellow activists, and that (along with cost) may have been why she was the only of the accused to be released on bail.

In a 2003 interview with XXL, Afeni noted that her bail was later revoked while she was pregnant. When she returned to jail, she advocated for herself while behind bars.

I always knew [Tupac] was special because from the moment he was conceived, God started blessing him. When I carried Tupac, when I was five months pregnant, they put me back in jail, my bail was revoked. When my bail was revoked, I was not allowed to have my own food. I could only have what was there. So I went and I got a court order so I could have a boiled egg a day—first it was to be fried, then they said to have it boiled—and a glass of milk a day. Tupac, in order to come, he was in my stomach in the worst possible living conditions. Jesus! Why would he want to be here under these circumstances? And remember that while I’m carrying him, I am not only locked up, but I am responsible for my own defense. I’m facing three hundred and forty something years in jail and I am my own lawyer. That’s what I chose to do.

And that’s what she did, representing herself during an eight-month trial. She delivered Tupac about a month after she and the others were acquitted.  

It was only years later that Afeni struggled with crack addiction and poverty—but her history as a money bail activist before and after incarceration often gets erased.

Money bail is essentially an act of ransom. It’s much more than a temporary tactic used to keep Black and Brown bodies and poor people behind bars. The long-term effects of mothers and caregivers spending even just a few days in jail consist of losing custody of their children, displaced housing, unemployment, and psychological trauma.

Today, organizations like Southerners On New Ground (for which I volunteer) and The National Bailout are preserving Afeni’s efforts through campaigns such as #ENDMONEYBAIL and #BlackMamaBailout. This year, I’m bailing out Black mothers and listening to Dear Mama with new ears. I hear it as a tribute to Afeni Shakur; all those who want liberation; families separated by mass incarceration; and those who know that when caregivers are in cages, families and communities suffer.

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