The Depressing, Predictable Caution and Calculation of Jay-Z


Many years back, when I wore a younger man’s clothes and print media was still a thing, I was working on an article for Spin magazine about the seeming incongruity of Hip Hop being a Left-Wing art form where the vast majority of discourse regarding abortion is fundamentally conservative. 

Deep into the process I got a note from my editor that essentially killed the piece. She said that another editor had looked at my article and argued that its underlying premise was invalid because the fundamental politics of Hip Hop are not left wing or socialist or anti-establishment but capitalist. 

I was, as you might imagine, very annoyed. At that point in my career, I desperately wanted to be in Spin. I can always use a paycheck and it fucking sucks to work hard on an article that dies an unmourned death. Yet I had to concede that the editor made a good point. In the late 1990s in particular, it was all about the Benjamins where mainstream Hip Hop was concerned, not overthrowing the ruling class. 

If anything, the objective for Hip Hop’s paper chasers was to make enough money to join the ruling class, not to destroy capitalism. 

I thought about the Spin editor’s line about Hip Hop’s politics being fundamentally capitalist when I read that Jay-Z had become Hip Hop’s first billionaire. This was no accident. From the very beginning, becoming as rich as humanly possible was always the goal for Jay-Z. 


There’s a reason Jay-Z’s label, Roc-A-Fella, was named after one of the richest families in the world. Jay-Z is, after all, a man who famously rhymed “I’m not a businessman, I’m a business, man.” 

Jay-Z wasn’t just a dude who was uniquely good at making money; he clearly saw himself as business personified. Jay didn’t do business; he was business. 

So when Jay-Z wore a Che Guevara shirt on his MTV Unplugged special and rapped on “The Bounce”, “September 11th marks the era of a revolutionary Jay Guevera” I couldn’t help but roll my eyes. 

Like college students the world over, Jay-Z was cynically wearing the clothing of an iconic badass with revolutionary politics he most assuredly did not share, being a huge capitalist and all.

Many years later Jay-Z pulled a similar stunt when he wore a custom-made Colin Kaepernick jersey when he was the musical guest on the season premiere of Saturday Night Live. 

Wearing Kaepernick’s jersey was supposed to illustrate that, despite his vast wealth and power, Jay-Z was still a rebel, still counter-cultural, still down for the struggle.  

Tell me more about this “Memphis Bleek.” Is he as talented as you say? And is it true that the “Roc” is in the building?

Tell me more about this “Memphis Bleek.” Is he as talented as you say? And is it true that the “Roc” is in the building?

It was a nice, if hollow gesture from a supremely cautious man in the enviable if complicated and tough position of trying to reconcile his ideals and credibility with everything that comes with BEING A FUCKING BILLIONAIRE. 

Because when it came time to live out his ideals, or at least his attire, Jay-Z and his many-tentacled organization Roc Nation chose to partner up, in a very big way, with an NFL establishment that has shut Kaepernick out for his principled stand against police brutality and racism. 

As an article on the NFL’s website blandly states, “Roc Nation, the entertainment company founded by rapper and businessman Shawn "Jay-Z" Carter, is entering into a multiyear partnership with the NFL to enhance the NFL's live game experiences and to amplify the league's social justice efforts.” 

Wow, sounds good and also vague to the point of meaninglessness! What does that mean? A press release quotes Jay-Z stiffly pontificating, “With its global reach, the National Football League has the platform and opportunity to inspire change across the country. Roc Nation has shown that entertainment and enacting change are not mutually exclusive ideas -- instead, we unify them. This partnership is an opportunity to strengthen the fabric of communities across America.”

They have fun! Forget money and power: Jay-Z is clearly in it for the LAFFS!

They have fun! Forget money and power: Jay-Z is clearly in it for the LAFFS!

The article ends with NFL commissioner Roger Goodell gushing about Jay-Z and the limitless possibilities of their partnership. 

Being a smart man, and a very careful man, Jay-Z has made sure to say many, if not all, of the right things regarding Kaepernick and his career-risking protest but actions speak louder than words and Jay-Z’s actions make him look like a hypocrite and a phony. 

The rapper has said of the kneeling that made Kap a controversial outlaw American icon, "I think we've passed kneeling. I think it's time to go to actionable items.”

Kaepernick, as you might imagine, was not pleased. He clearly felt that the bond between an athlete and a billionaire rapper who wears his uniform to look cool on television was more sacred than it ultimately proved to be. 

He was especially not pleased that Jay-Z did not run the whole, “Hey, the NFL called me up and said, “We want you to make us look good and help us solve our Colin Kaepernick problem. You in?” thing by him before the world learned that Jay-Z was going into business with the NFL.

This is entirely in character for Jay-Z. He’s always been pragmatic and calculating. That’s how you become a billionaire. That’s also what makes his partnership with Kanye West so fascinating and electric. They could not be more different. Kanye is incapable of self-censorship. He’s spontaneous, intense, living forever in the white hot heat of the moment. Jay-Z, in sharp contrast, is cool and calm, forever calculating the odds and playing the angles. 

And now that angle-playing has led him to go into business with the rich white billionaires that own the NFL.

Jay-Z didn’t just become a billionaire and one of our most highly regarded artists because he’s brilliant as both a rapper and a businessman. No, he’s held in such high esteem because he stands for something more than just making money, although, heaven knows, he stands for that as well. 

Jay-Z’s pact with the NFL calls his character and integrity into character. Jay-Z was clearly angling for a place at the table, for a chance to change the system from the inside, or, at the very least, enjoy the perks of being part of the system, including, it was rumored, a chance to become a part-owner of an NFL team. 


Then rumors spread that Jay-Z would most assuredly not be getting part ownership in an NFL team despite his high-profile relationship with the league, which just underscores the high price Jay-Z is willing to pay to get into the NFL business at a time when it stands (no pun intended) for everything he’s supposed to be against as an icon and artist as well as a businessman. 

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