Jay-Z rarely, if ever, receives backlash. He is frequently heralded as one of the greatest rappers of all time. He made billions from his music and business dealings. He’s also seen as a model for thriving as a Black man in America. However, after controversial partnerships with Target and the NFL, certain people have criticized how much he truly represents his communities.
But surely, all that money might cushion the mean comments. Is it even possible for him to feel guilty about anything with that much luxury? According to former NFL star Colin Kaepernick, he just might.
Back in July 2026, Jay-Z freestyled during one of his massive Yankee Stadium shows, mentioning the former San Francisco 49ers quarterback. “They run out of characters, had to bring back up [Kaepernick] again,” Hov shrugged. “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 [the NFL] can’t control.”
In the background, Colin Kaepernick has been critical of Jay-Z’s partnerships, particularly with the NFL. Now that the New York legend has invoked his name again in the freestyle, the former athlete posited to NBC News if Hov actually feels more guilt than he lets on.
Does Jay-Z Actually Feel Guilty Over His NFL and Target Brand Deals?
“First and foremost, what it speaks to is power of people,” Kaepernick said about the backlash to Hov. “The backlash that [Jay-Z] received for partnering with the NFL and going counter to people’s interests in 2019 was a major problem for him, so much so that he’s still bringing it up in 2026.”
Then, Colin Kaepernick argued that Jay responding at all suggests his conscience is bothering him. “People are now realizing, ‘Why are you so comfortable stepping into these positions that are counter to the positions that people on the ground actually want?’” He continued. “And to me, I view that as speaking to a guilty conscience and trying to reposition or reframe the conversation.”
Kaepernick concluded by noting that Jay-Z is one of many people working to tarnish his name. Moreover, he said that he understood but doesn’t have to agree or speak out every time someone mentions him.
“I understand why he’s trying to do reputational recovery, I get it. I don’t agree with the actions,” he said of Jay-Z. “But I’m also not gonna respond to everything that’s said about me, because I also believe the actions and the work that I do will speak for themselves.”
Photo by Catherine Ivill – AMA/Getty Images
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