The Ancestral Gaze: What Would Harriet Tubman Think of Wiz Khalifa?

A "Bargain Bin" Blog Post by Hilerie Lind

I was lying in bed last night, exhausted. Not the kind of tired that sleep can fix, but the kind that settles into your bones when you've spent too many days watching the world burn and wondering how we got here.

I turn on Finding Your Roots. It's one of my favorite shows. I love ancestry. I love history. I love watching Black people discover the resilience of their ancestors, the land they owned, the names they carried, the lives they built out of nothing. It feels like home.

But last night, I almost turned it off.

Because the episode featured Wiz Khalifa. And I used to like him. Back in 2009, 2010, 2011, when I was living in Columbus, I'd hear his songs when we went out. "Black and Yellow." "On My Level." He was part of the soundtrack of that era. But in this MAGA era, he's proven himself to be a disappointment. Just like his son's mother, Amber Rose, is to the culture.

So I started not to watch. But then I saw that Sanaa Lathan was also featured, and I love her. She's conscious. She's intentional about the roles she chooses. Love & Basketball. Brown Sugar. Nappily Ever After. Something New. She is a woman of the culture. She has not sold out.

And then it hit me: I'm not too fond of the host of the show like I used to be either.

Henry Louis Gates Jr. I used to admire him. I used to see him as a giant in Black intellectual thought. But after I engaged with the Black Canon Debate, I was thoroughly disappointed. And then I learned that he was inducted into the Sons of the Revolution, an organization that celebrates colonial and early American heritage, including ties to the very systems that enslaved our ancestors. In the Black Canon Debate, he and Houston Baker Jr. advocated for the use of Eurocentric literary theory to analyze Black literature, a position that Joyce Ann Joyce argued was a betrayal of the Black community.

But I decided to watch anyway. Because I needed to understand something. I needed to understand how a man like Wiz Khalifa, a man whose ancestors fled the lynchings of the South, whose ancestor fought in World War II to protect a country that did not protect him, could align himself with a political movement that terrorizes Black and Brown people.

And what I witnessed was not just disappointing. It was devastating.

What Would Harriet Tubman Think?

As I watched Wiz Khalifa sit in that room, learning about his ancestor Howard Williamson, a Black man who registered to vote in Alabama in the years following the Civil War, a time when the Ku Klux Klan was lynching Black people for daring to exercise their rights, I kept asking myself: What would Harriet Tubman think of Wiz Khalifa?

What would she think of a man who inherited the freedom his ancestors died for, and then chose to align himself with a political movement that seeks to eradicate that freedom?

What would Malcolm X think? What would Martin Luther King Jr. think? What would Fred Hampton think?

These were people who sacrificed everything for collective liberation. Harriet Tubman carried a gun on the Underground Railroad, not just to protect the freedom seekers from slave catchers, but to protect them from each other. Because she knew that fear, desperation, and the promise of reward could turn a brother into an informant.

Malcolm X was assassinated for refusing to compromise his principles. Martin Luther King Jr. was assassinated for demanding that America live up to its promises. Fred Hampton was murdered in his bed by the FBI for organizing Black people to fight for their own liberation.

And Wiz Khalifa? He sits in a room, learning about his ancestor who risked his life to vote, and his response is... what? A casual "That's crazy"? A lack of nuance? A disposition that suggests he doesn't fully grasp the weight of what he's witnessing?

I watched him sit there with his glasses on, cursing casually, and I thought: This is what happens when you inherit freedom without understanding the price that was paid for it.

Wiz and Ava

And then came the moment that crystallized everything for me.

Wiz Khalifa found out that he has a DNA cousin: Ava DuVernay.

Let that sit with you for a second.

Wiz Khalifa and Ava DuVernay share the same bloodline. They are descendants of the same ancestors who fled the lynchings of the South, who fought in World War II, who registered to vote in the face of the Ku Klux Klan.

But they occupy opposite ends of the cultural and intellectual spectrum.

Ava DuVernay is a filmmaker who has dedicated her career to telling the stories of Black people with dignity, nuance, and power. She directed Selma, a film about Martin Luther King Jr. and the fight for voting rights. She directed 13th, a documentary about the prison-industrial complex and the ways that mass incarceration is a continuation of slavery. She created When They See Us, a series about the Central Park Five and the ways that Black boys are criminalized and dehumanized by the justice system.

Ava DuVernay is using her platform to honor the sacrifices of her ancestors and to fight for the liberation of Black people.

And Wiz Khalifa? He's aligned himself with Amber Rose, a woman who spoke at the Republican National Convention in support of Donald Trump. He's aligned himself with a political movement that terrorizes Black and Brown people, that separates families, that deports immigrants, that emboldens white supremacists.

This is the irony of the DNA cousin. Two people who share the same bloodline, but one is fighting for liberation and the other is complicit in oppression.

The Chaos of Complicity

And this is not just about Wiz Khalifa. This is about the moral maze we are living in right now.

A lot of Hispanic people voted for Trump. There are a lot of Black and Hispanic ICE agents. They are contributing to the chaos. They are participating in the terrorizing of their own communities.

And I keep asking myself: How do you not see the destruction you are participating in?

How do you, as a Hispanic person, vote for a man who has called Mexican immigrants "rapists" and "criminals"? How do you, as a Black or Hispanic ICE agent, participate in the deportation of families who look like you, who share your history, who are fleeing the same violence and poverty that your ancestors fled?

How do you inherit the sacrifices of your ancestors and then choose to betray them?

This is the Faustian Bargain in action. This is what happens when proximity to power becomes more important than accountability to the people. This is what happens when you believe that your individual success is more important than the collective survival of your community.

The Black Canon Debate

Back to the Black Canon Debate. It's one of those intellectual moments that haunts me because it reveals so much about the choices Black intellectuals make when they achieve proximity to power.

In that debate, Joyce Ann Joyce argued for a "For Us, By Us" (FUBU) directive for Black intellectual thought. She argued that when Black intellectuals prioritize white institutional powers over the Black academy, they become what society coerced them into. They misinterpret success for collective advancement. They sell their souls to be accepted by white institutional powers.

And Gates and Baker? They advocated for the use of Eurocentric literary theory to analyze Black literature. They demanded that Black literature be scrutinized through the use of Ivy League tools. They stood firm in their belief that Black value can only be dictated through these same Ivy League institutions.

Joyce called this what it was: intellectual assimilation. A betrayal of the community. A desire to take on Eurocentric ideals as a way to progress, separating Black intellectuals from Black cultural awareness and pride and toward a structure that relies on the approval of white intellectualism.

And I agreed with her then. And I agree with her now.

Because what Joyce was naming in 1987 is the same thing I'm naming in 2026: the Faustian Bargain. The belief that proximity to white power, to white institutions, to white approval, will save you. The belief that you can "make it" by distancing yourself from Blackness, by erasing your past, by choosing the Ivy League over the cookout.

But it never saves you. Because the terms of the bargain are always rigged. The devil always collects.

The Destruction They Participate In

When I think about Amber Rose and Stacey Dash, I don't think about them as anomalies. I don't think about them as women who are "confused" or "lost." I think about them as women who are actively participating in the destruction of Black and Brown people.

Let me be clear about what I mean.

Amber Rose is a mixed woman, Black and white, who has built a career on proximity to Black culture. She dated Kanye West. She dated Wiz Khalifa. She had a child with Wiz. She has profited from Black men, Black aesthetics, and Black cultural capital.

But in 2024, Amber Rose spoke at the Republican National Convention in support of Donald Trump. She stood on that stage and endorsed a man whose administration has terrorized Black and Brown people. A man whose policies have separated families, deported immigrants, and emboldened white supremacists. A man whose rhetoric has made it clear that Black and Brown lives are expendable.

And Amber Rose stood there and said, "I support this man."

This is not just a political disagreement. This is not just a difference of opinion. This is active participation in the destruction of Black and Brown people.

Because when you support MAGA, you are supporting ICE raids that tear families apart. You are supporting policies that cost Black women their jobs. You are supporting a system that views Black and Brown people as collateral damage. You are supporting the kidnapping of foreign presidents, the bombing of Nigeria, the terrorizing of Black and Brown communities across the world.

And Amber Rose knows this. She is not naive. She is not ignorant. She is a grown woman who made a choice. She chose proximity to power over accountability to the people.

And Stacey Dash? She's been making that same choice for years. She's a Black woman who has built a career on attacking Black people. She's called the NAACP "outdated." She's said that Black History Month is "ridiculous." She's aligned herself with Fox News and conservative talking heads who view Black people as a problem to be solved, not a community to be uplifted.

This is not just "respectability politics." This is betrayal. This is the Faustian Bargain in action. This is what happens when mixed women and Black women choose proximity to whiteness over accountability to Blackness.

Why Don't Our Black Men See Us?

But this isn't just about Amber Rose and Stacey Dash. This is about the Black men who have abandoned us.

Wiz Khalifa. Henry Louis Gates Jr. Kanye West. Ray J. The countless Black men who have chosen proximity to power over accountability to the people.

Why don't they see us?

Why don't they see that we are exhausted? Why don't they see that we are holding it down, that we are absorbing the violence, that we are being terrorized by ICE raids and MAGA policies and the daily trauma of living in a country that views us as collateral damage?

Why don't they see that when they choose proximity to power, when they support MAGA, when they join organizations that celebrate colonial heritage, when they advocate for Eurocentric literary theory over the FUBU principle, they are choosing the system over us?

The Question We Must Sit With

I don't have an answer. I don't have a solution. I don't have an action plan.

I just have this question: What would Harriet Tubman think of Wiz Khalifa?

What would she think of a generation that inherited the freedom she died for, and then chose to squander it?

What would Malcolm X think of Black and Hispanic ICE agents who participate in the terrorizing of their own communities?

What would Martin Luther King Jr. think of Black intellectuals who choose the Ivy League over the cookout?

What would Fred Hampton think of Black men who choose proximity to power over accountability to the people?

Sit with that.

Hilerie Lind is a PhD student in Africana Women's Studies at Clark Atlanta University and the author of "What If I Told You I Was Worthy Before?" She writes about the intersection of Black Feminist Theory, hip-hop culture, and the gendered politics of "selling out" in Black communities.