Colin Kaepernick is the one battle Jay-Z can’t win

Jay-Z started 2026 with a mission: He’s going on the offensive. He was no longer going to stay silent about the people who had insulted him over the past few years, nor was he going to sit down and take the rumors and false narratives about him. Most of us could pinpoint the people he was talking about, ranging from Dame Dash and his sexual assault accuser to Nicki Minaj and Drake.

Many of the targets — no pun intended — seemed clear, but Jay-Z taking aim at Colin Kaepernick over the summer was unexpected. The resulting back-and-forth has largely left the rapper on the defensive, lacking a simple retort to quell the criticism.

For the first time in his long career, Jay may have embarked on a crusade he can’t win.

The Jay-Z and Kaepernick split seemed to start back in 2019. Kaepernick, the former NFL quarterback, had been famously exiled from the league after the 2016 season, when he knelt during the national anthem to bring attention to racial inequalities and police brutality in America. He settled his dispute with the league in early 2019.

Soon thereafter, Jay-Z, who had also spent the previous few years using his voice to speak up about social justice causes — including wearing a Kaepernick jersey for a Saturday Night Live appearance in 2017 — agreed to be the face of the NFL’s social justice rebrand. The NFL would partner with Jay’s Roc Nation to create Super Bowl halftime programming and support the league’s Inspire Change and social justice initiatives.

The news conference, full of photos of Jay-Z and NFL commissioner Roger Goodell laughing together and dapping each other up, was one of the most criticized moves of Jay-Z’s career to date.

To make matters worse, Jay-Z added comments that were, at best, dismissive of Kaepernick. His assertion that “we’ve moved past kneeling” became a phrase that signaled a divide between the rapper and businessman’s capitalistic approach and Kaepernick’s sacrificial revolution.

Kaepernick has famously stayed mostly silent about the NFL and Jay-Z for the better part of a decade, letting the public speculate about everything from his philosophies to his real feelings about the partnership. But in that silence, Jay-Z decided to strike first.

Before his New York concerts in July, news spread that Target would sell re-releases of Jay-Z’s albums.

The retailer has been under fire and the subject of boycotts across the country because of newly adopted policies seen as anti-DEI. Jay-Z seemingly engaging in a partnership with Target reignited the debate over whether he is a pro-Black businessman or simply focused on the bottom line. It also revived debates over his NFL deal and sparked more speculation about his relationship with Kaepernick.

So, as promised, Jay-Z took the offensive with a freestyle at one of his Yankee Stadium shows in July: “Buddy took a check, I ain’t even mad at him, but along with that check you have to sign a non-disparagement. I’m the one they can’t control.”

The barbs at Kaepernick and critics of Jay-Z’s activism were the flimsiest of the night. First, there was no real reason to drop a “diss” aimed at the former football player. According to reports, he didn’t even sign a non-disclosure agreement with the league.

Then there was this: “You shopping at Amazon or you boycotting? You posting on Instagram — that’s Meta, boy, stop it. Y’all know Google owns YouTube. You picking and choosing the politicking as usual.”

It was a misreading of the situation. For starters, Jay-Z isn’t a corporation, and shaming fans without the means he has to use products that essentially have monopolies isn’t nearly the same as his partnership with Target. For a genius like Jay-Z, whose meticulousness with every bar has become part of his legend, delivering a half-cocked response that sounds disconnected from reality reeked of a man ill-prepared to match Kaepernick’s wits and philosophy on this stage.

Then it was Kaepernick’s turn.

As part of his rollout for his memoir, The Perilous Fight, Kaepernick, 38, has finally broken his silence. He said Jay has a “guilty conscience” about his own dealings with the NFL and Target, which caused him to lash out. However, it was his appearance on What Now? with Trevor Noah, where he told his side of the story. If true, his side is incredibly damning.

According to Kaepernick, he reached out to Jay-Z after the MC wore his jersey on SNL. Jay never responded to a meeting request, but later wanted Kaepernick to go on stage and kneel during a performance of “The Story Of O.J.”

Kaepernick’s recollection of hearing about Jay-Z’s NFL deal is the most interesting, especially the notion that the league sought a prominent Black figure to soften the post-Kaepernick protest backlash. They landed on Jay-Z. The two men had a conversation about it after the “we’re past kneeling” comments.

As Kaepernick recalls: “I was like, ‘I completely disagree with what you’re doing. And you’re selling the culture out to people who do not care about the culture.’ And he was like, ‘Well, the ink is dry.'”

Kaepernick’s story, if true, only affirms the concerns raised when Jay-Z first made the NFL deal. At the time, it felt like Jay-Z’s capitalism had overridden his desire for true disruptive social change. And since then, we haven’t seen much in his NFL deal that looks like it’s brought the league closer to meeting Kaepernick’s demands. Instead, it did serve to paper over the league’s sins and make us sing and dance along with Super Bowl halftime shows as if nothing happened.

Kaepernick has also accused Roc Nation of leaking false information to media outlets about his moves, aiming to get them to write “hit pieces” on him.

Jay-Z has yet to respond to Kaepernick’s accusations either via freestyle or interview. Beyond proving that Kaepernick is outright lying, I’m not sure what version of the story can paint him in a more favorable light than the guy committed to the work and actively turning down more money to choose another path.

It’s always going to be a tough sell for a billionaire to convince people he’s more for a cause than someone with a fraction of his earnings who’s also put his career on the line.

Jay-Z has always purported to be about the greater good of Black folks. And the most generous reading of his actions is that he is dedicated to that cause. Even the NFL deal itself. I do think Jay-Z thought he was progressing toward the next step in the protests.

He said so himself: “No, I don’t want people to stop protesting at all,” he said in 2019. “Kneeling is a form of protest. I support protest across the board. … I’m not minimizing that part of it because that has to happen, that’s a necessary part of the process. But now that we all know what’s going on, what are we going to do? How are we going to stop it? Because the kneeling was not about a job, it was about injustice.”

I think Jay-Z’s moves have always been couched in the belief that it will be best for all of us. Maybe that’s an idealism and naivete on my part. But I tend to believe Jay-Z’s heart is in liberation. He may even believe his NFL partnership and the halftime shows that are part of it have elicited the change he sought to execute.

The problem is that the partnership still clashes with what Kaepernick and the original protesters were fighting for. The problem is that Jay-Z’s liberation is tied to corporate partnerships, capitalism and the pursuit of billions. It’s an ideological difference, and one that Jay hasn’t budged from or seemed invested in evolving beyond.

A common response to the two men’s issues has been to position them as two sides of the same activist coin.

Jay, though, has always tethered his version of liberation to capitalistic earnings, especially capitalistic earnings that line his pockets. The guy who rapped “gentrify your own hood” just might not have the range to talk that talk with a guy who’s dropping Frantz Fanon quotes on podcasts. The best course of action is a Jay-Z willing to listen and adapt his approach in a way that benefits the whole.

He just hasn’t found that desire quite yet.

Ironically, Kaepernick tearing away at Jay’s activism is happening at a time when we’re reminded of the rapper’s singular brilliance as an MC. His new show, Jay-Z in 8, a series of interviews with record producer Rick Rubin breaking down songs and lyrics, reminds us that we’re in the presence of one of the great poets of our lifetimes.

It’s also a reminder of what it looks like to see Jay-Z love. He loves the spoken word. He loves the music and its history. He loves every syllable enough to pore over each one he’s ever rapped over the course of 30 years. He loves the art. And he’s rewarded the art by being one of the best ever.

That meticulous, art-honoring genius was absent for the few minutes he was on stage throwing out lazy comparisons at Kaepernick.

Instead, he was a man trying to will himself to victory in the court of public opinion, rather than working toward victory for the people who have spent their money propelling him to the billionaire status he so covets. That disconnect is where he loses the battle — and where the gulf between his shortcomings and Kaepernick’s movement work resides.

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