A letter from a disappointed Black millennial.
Dear Jay-Z,
For most of my life, you weren't just one of my favorite rappers — you were one of my heroes. Like so many Black millennials who grew up in neighborhoods where opportunities were scarce but dreams were limitless, I saw you as proof that someone who looked like me could build something bigger than the streets we came from.
You didn't just rap about money. You rapped about ownership.
You didn't just talk about surviving. You talked about building.
You didn't just tell us to hustle. You made us believe that hustle could become freedom.
For years, I believed every word.
As a kid, your music taught me confidence. As a young man, it taught me ambition. And as I became an activist, I believed your success represented something bigger than individual wealth. I believed you were opening doors that had been locked for generations. I believed you wanted to become the first Black billionaire not simply to make history, but to make sure you weren't the last.
I thought you were one of us. That's what disappoints me the most.
Looking back, I realize I wasn't just listening to your music. I was buying into an image. You weren't presented as another rapper chasing money. You presented yourself as something much bigger.
On one track, you compared yourself to Che Guevara, jewelry and all. Che Guevara wasn't a businessman. He was a revolutionary whose image has become synonymous with resistance to capitalism and imperialism. Whether people agree with his politics or not, invoking his name carries meaning. It tells listeners you identify with revolutionary ideals.
Then there was another line that carried just as much weight — one where you rapped that you arrived the same day Fred Hampton died. Fred Hampton wasn't just another historical reference. Hampton dedicated his life to organizing poor Black communities, building solidarity across racial lines, and confronting systems of oppression. He was assassinated because many believed his organizing posed a threat to the status quo.
When you invoke figures like Che Guevara and Fred Hampton, you aren't just making clever rap references. You're placing yourself in a tradition of people who stood with ordinary people against powerful institutions.
As Black millennials, many of us believed you.
We didn't just hear bars.
We heard leadership.
We heard someone who understood that Black liberation meant more than becoming rich.
As I got older, though, I stopped listening only to the music and started paying attention to the man behind it.
That's when everything changed.
The first cracks didn't come from an album.
They came from your decisions.
When Colin Kaepernick sacrificed his NFL career by kneeling against police brutality, millions of Black Americans understood that his protest was about something larger than football. Many people boycotted the NFL because they believed the league had blackballed a man for standing on principle.
Then you partnered with the NFL.
When you stood beside Commissioner Roger Goodell and declared, "We're past kneeling," I remember wondering: Who decided that? Certainly not the families still burying loved ones. Certainly not the activists still marching. Certainly not the people who believed Kaepernick's protest was never about kneeling in the first place. It felt like the movement had become negotiable once there was enough money on the table.
Years later, you doubled down in your music, rapping about a friend who "took a check" — pointing out that along with that check came a non-disparagement agreement. Maybe you intended it as commentary. Maybe you were challenging a narrative. But to me, it landed differently. It sounded like you were reducing Colin Kaepernick's sacrifice to a business decision rather than recognizing the cost of what he gave up. Whether listeners agree with that interpretation or not, it reinforced a larger pattern I had begun to notice: when movements collided with money, your analysis often centered on the deal.
Then came the moment that completely changed my perspective.
Target.
As Black communities organized boycotts over Target's rollback of Diversity, Equity, and Inclusion initiatives, I expected one of the most influential Black businessmen in America to wrestle publicly with that tension.
Instead, you announced an exclusive Reasonable Doubt vinyl through Target. When people questioned the decision, your response wasn't to acknowledge why Black consumers were upset. Instead, you turned the spotlight back on us — rapping that the Target deal was no different from what Apple and Walmart already do, and asking whether people boycotting Target were also willing to give up Amazon, Instagram, Meta, and Google's YouTube, accusing critics of picking and choosing their politics as usual.
That was my wake-up call.
Instead of asking whether your own choices aligned with the values many of us believed you represented, you challenged the consistency of everyday people trying to navigate an economy where avoiding every corporation is practically impossible.
You shifted the burden from one of the most powerful Black businessmen in America onto ordinary consumers.
That isn't leadership.
That's deflection.
The more I thought about it, the more I realized that what you had always sold us wasn't collective liberation. It was individual escape.
You taught my generation that ownership was the revolution. That becoming wealthy was the highest form of Black empowerment. That capitalism itself could become liberation if enough Black people won at it.
For years, I believed that message.
Today, I don't. Because following the Jay-Z blueprint doesn't lead to collective freedom.
It leads to individual accumulation.
It tells every kid from Marcy Projects to dream of becoming the billionaire instead of asking why billionaires exist in the first place.
I no longer believe there are ethical billionaires. Not because wealth itself is evil, but because accumulating that level of wealth almost always requires participating in systems that concentrate power and resources in the hands of a few while everyone else competes over what's left. Black faces can occupy those systems, but that alone doesn't transform them into instruments of liberation.
Some people will read this and accuse me of expecting you to save Black America.
That's not what I'm asking. I never expected you to solve racism. I never expected you to carry every movement on your back.
But I did expect consistency.
If you're going to invoke Che Guevara, understand what he represented. If you're going to invoke Fred Hampton, understand what he died for. If you're going to present yourself as someone who "can't be controlled," don't be surprised when people question partnerships that appear to align with the very institutions many activists were challenging.
As a Black millennial, you didn't just sell me music.
You sold me a philosophy.
You told us ownership was freedom.
You told us economic success was the revolution.
You wrapped that message in the language of Black resistance, self-determination, and revolutionary icons. Looking back now, I realize the revolution you described always had one beneficiary. We were taught to admire the billionaire more than we were encouraged to build communities that no longer needed one.
I still believe Jay-Z is one of the greatest rappers to ever touch a microphone. That isn't what disappoints me.
What disappoints me is that he taught my generation to believe wealth and liberation were the same thing.
But whenever Black political movements collided with corporate interests, Jay-Z consistently found himself sitting on the side of capital.
We believed Jay-Z was showing us how to free the people.
Maybe he was only ever showing us how to free himself.
— Anthony Simmons
