Why Cassandra Wilson’s Music Deserves To Be The Legacy We Honor [Op-Ed]

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Remembering Cassandra Wilson, like so many of our artists who have passed on, means sitting with all of who they were. When I learned Cassandra had passed away this week, I felt conflicted. I was a longtime fan who loved her music, but in recent years I made a conscious decision to step away when Cassandra’s personal politics moved toward the MAGA movement.  

The first time I heard Cassandra Wilson’s voice, I was completely spellbound. I was in college and deeply entrenched in learning all I could about Black women jazz vocalists. One of my professors, Dr. Farah Jasmine Griffin, who was writing about Billie Holiday at the time, urged me to listen to Cassandra. 

Up until Farah’s recommendation, my ears were still learning the heavyweights of the canon like Billie Holiday, Sarah Vaughan, Abbey Lincoln, and Ella Fitzgerald. Farah suggested Cassandra as a crucial expansion of my learning and that lineage, and the moment I heard her voice, I understood why. 

There was something about the fullness in Cassandra’s voice and the way she, like Billie Holiday before her, could wrap her voice around music while capturing the full range of Black life. 

When she remade Billie Holiday’s “Strange Fruit,” Cassandra’s version let the grief of lynchings stretch out through her voice as if she were traveling through a sonic time machine and reaching back into that era itself, her timbre carrying the trauma and terror, as well as the unrequited reckoning and embodied remembrance those horrors had passed along through generations. 

The more I listened, the more hooked I got. Cassandra quickly emerged as my favorite contemporary jazz vocalist. I took the train into downtown Philly to a record store to buy Wilson’s CDs. I read any and every interview about Cassandra I could get my hands on. This was the mid-90s, and the jazz heads knew Cassandra and lauded her early work, but the mainstream world hadn’t fully discovered her yet. 

It wouldn’t be until 1997 that she won her first Grammy, for the album New Moon Daughter. We were still years away from Time Magazine becoming so enthralled with her deep contralto that it named her America’s best singer in 2001, and Cassandra would have to wait until 2009 to be awarded her second Grammy, for the album Loverly.

My love of Cassandra and her music grew even deeper once I moved to New York City after college. Farah moved to the city not long after I did, and one of the things we loved doing was seeing live music. Cassandra topped our list of musicians to see live. We caught her at the Blue Note, Carnegie Hall, and wherever else she performed. 

This week, Farah was the first person I texted when Cassandra died. For this article, I asked her about her favorite memories of Cassandra. “To see her live was to experience her full artistic powers,” she shared. “A musician communing with other musicians, turning jazz clubs, concert halls, and outdoor venues into ritual space.”

Farah and I would call our sojourns to see Cassandra perform a form of church. We showed up dutifully and open to being led wherever her voice and set decided to take us that night. Cassandra’s voice consistently expanded my sense of self, connecting me to spirit in a way that always delivered me back to what felt like a new, more grounded, and whole version of myself. 

For me, her music had been a constant presence and influence for years. When my best friend died after a brief illness, it was Cassandra’s music that I turned to for solace. “Solomon Sang” carried me through my grief with its telling of a king who seemingly had everything, yet still bore a private sorrow nobody around him could fully see. Cassandra’s rendition of Hank Williams’s “I’m So Lonesome I Could Cry” captured the grief that consumed me and held it with a strength I didn’t have in me to hold on my own. 

Her range came through in her playfulness and ability to capture sensual moments, too. That part of her could be heard in the song,  “A Little Warm Death,” a title that plays on la petite mort, the French phrase for an orgasm as a small dying. Over a tango-tinged bed of violins, Cassandra coaxes someone toward surrender in a low, unbothered seduction, the chorus repeating and the violins climbing faster and faster until the violins and her voice cut off all at once, the abrupt ending the climax. 

Farah said that part of Cassandra’s genius was found in her ability to expand beyond genres. “She refused to be bound by generic categories. She found great freedom in jazz but also erased generic boundaries. Her impact on music is yet to be fully realized.” Over the span of her career, she covered songs by artists ranging from Neil Young to Cyndi Lauper to Miles Davis to U2.

Somewhere along the way, a new layer of Cassandra emerged, shifting much of the conversation away from her music and legacy and onto her political worldview. Her social media feeds revealed her support for Trump, Kanye West, RFK Jr., and anti-vaccine rhetoric, all filtered through her own description of herself as an independent thinker. 

Her insistence on trusting her own perception ran through both halves of her life. In her music, it produced genius and boundary-breaking work, and came with a rare ability to capture the essence of Black life and emotion in every register her voice could reach. Pointed at medicine and politics, it aligned her with misinformation and movements that worked against the Black community she’d spent much of her career giving voice to.

Her legacy will forever carry an asterisk because of her political views. Cassandra has no more political votes left to cast or political rhetoric to share, and there’s a short runway for mulling over all of her politics now that she’s gone. 

What is very much alive even after her passing is perhaps her most powerful and sustaining legacy: her music. She was a musician after all, and music is the one place where her love for us and her ability to capture the full range of our humanity will forever be tangible and available to us to consume. This is true even as we may still see her politics as a cautionary tale and wrangle with ourselves about the person she was behind the music.  

In the hours after I learned Cassandra had died, the responsibility of writing about these conflicts set in. Capturing who she was, weighing the political conservatism that still riled me against the profound impact her music had had on me, and reconciling the years I’d stopped listening to her altogether was overwhelming. Revisiting her music for the first time in nearly a decade felt like being pulled back in by a first true love who’d loved me hard, then did the unthinkable- someone I’d sworn off years ago and who was gone now anyway, past the point where any of it could be resolved between us. The pain still lingering, I found myself not wanting to write a single word. 

Thinking all I needed was to clear my head, I got in my car to grab lunch. As I parked at one of my favorite restaurants, a dragonfly appeared and circled my car several times, hovering until I got out. Later, when I came back to my car, got in, and secured my seatbelt, it returned, flying even lower this time. Its circling felt deliberate enough to be a sign I needed to pay attention to. 

Spiritually, dragonflies have long symbolized transformation, a life spent underwater before emerging to fly. They have close to 360-degree vision, and in many Native traditions, they’re seen as creatures with the gift of seeing through illusion to a deeper truth. 

Unlike other insects that swarm, they find their way solo, guided by an inner compass the way Cassandra seemed to have been. I learned recently that dragonflies usually don’t return after their first visit. That this one did made me feel it was important to push past the grief, the conflicted feelings, and write about her in a way that afforded her both context and grace.

Dragonflies carry light, too. Their wings catch it and throw it back to us in flashes of color. That’s what Cassandra’s music can be for all of us now. A bright light whose voice and music we keep trying to catch and hold onto for as long as we can. How blessed are we as music lovers that with Cassandra, all we have to do to revel in her light is press play. 

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