Ten years after going head-to-head with the NFL, Colin Kaepernick is telling all. One of the more riveting passages in Kaepernick’s new memoir, The Perilous Fight, involves his relationship with Jay-Z.
Kaepernick was one of the premier quarterbacks in the NFL during the first part of the 2010s. He led the San Francisco 49ers to the Super Bowl in the 2012-13 season. In 2013-14, he was sensational as he threw for 3,197 yards and a career-high 21 TDs. He also ran for 524 yards that season. The next season he was just as good, throwing for a career-high 3,369 yards and 19 TDs while rushing for a career-high 639 yards.
Despite that on-field success, Kaepernick has not played in an NFL game since New Year’s Day 2017. In the Niners’ 25-23 loss to the Seahawks, Kaep completed 17 of 22 passes for 215 yards and a touchdown.
Many believe that the quarterback has been blackballed by the NFL after he began kneeling during the national anthem to protest police brutality and racial injustice.
Jay-Z publicly stood behind Kaepernick in the few years that followed. In August 2019, however, Jay-Z’s Roc Nation partnered with the NFL on entertainment, including Super Bowl halftime show curation.
Kaepernick says he spoke with Jay-Z directly, for the first time ever, shortly after the rapper’s deal with the NFL was done.
“[Jay-Z] tells me he did the deal [with the NFL],” Kaepernick said this week on All The Smoke. “I was like, ‘I disagree with what you’re doing. You’re selling the culture out to a bunch of racists … And he was like, ‘Well, the ink’s dry.’”
But here’s a lot more to this story—much has gone down in the last decade. This is A Timeline of Jay-Z and Colin Kaepernick’s Relationship.
August 26, 2016 — The Protest
Following the San Francisco 49ers’ third preseason game, Steve Wyche of the NFL Network noticed Kaepernick sitting on the bench during the playing of “The Star Spangled Banner.” He asked him about it during a post-game interview.
Kaepernick, who’d been vocal on social media throughout the summer posting about the fatal police shootings of Philandro Castle and Alton Sterling and other alleged instances of police brutality, explained his stance."I am not going to stand up to show pride in a flag for a country that oppresses black people and people of color. To me, this is bigger than football and it would be selfish on my part to look the other way. There are bodies in the street and people getting paid leave and getting away with murder"
September 1, 2026 — Kaep Takes A Knee
Kaepernick, along with teammate Eric Reid, kneel during the playing of the national anthem prior to the 49ers final preseason game. Kaepernick pivoted following a conversation with former NFL player Nate Boyer, a former member of the Army’s Green Berets.
Deflecting claims that his protest disparaged the military, Kaepernick announced that he’s donating a million to various charitable organizations. “Once again, I’m not anti-American,” Kaepernick said. “I love America. I love people. That’s why I’m doing this. I want to help make America better. I think having these conversations helps everybody have a better understanding of where everybody is coming from.”
Spring 2017 — The Empire Strikes Back
After a 2-14 season, the 49ers inform Kaepernick they intend to release him. Kaepernick opts out of his contract but goes unsigned league-wide, leading to allegations that NFL owners are blackballing him for his advocacy.
September 15, 2017 — Enter Jay-Z
During his set at the Meadows Music and Arts Festival at Citi Field in Queens, New York, Jay-Z dedicates "The Story of O.J." to Kaepernick: "I want to dedicate this song to Colin Kaepernick tonight... to anyone that was held back and you overcame."
September 2017 — Jay-Z Stiff Arms the NFL
Jay-Z reportedly turned down the NFL's offer to headline the Super Bowl LII halftime show, which is widely read as a show of solidarity with Kaepernick.
September 30, 2017 — Live From New York
While performing"Bam" with Damian Marley on Saturday Night Live, Jay-Z wears a black No. 7 jersey and turns around mid-song to reveal "Colin K" on the back. No statement, no kneeling—just the reveal.
October 2017 — Kaepernick Rebuts
Kaepernick files a grievance under the NFL’s collective bargaining agreement, alleging that NFL owners colluded against signing him to an NFL contract.
The filing states that the NFL and its owners, “have colluded to deprive Mr. Kaepernick of employment rights in retaliation for Mr. Kaepernick's leadership and advocacy for equality and social justice and his bringing awareness to peculiar institutions still undermining racial equality in the United States."
November 12, 2017 — Jay Doubles Down
During the Miami stop of the 4:44 tour, Jay tells the crowd, "I want y'all to understand, when people are kneeling and putting their fists up, and doing what they're doing, it's not about a flag. . . It's about justice, it's about injustice. And that's not a black or white thing— it's a human issue."
January 27, 2018 — Sting Like a Bee
During an appearance on CNN's The Van Jones Show, Jay-Z goes further, saying he'd advise Kaepernick "100%" to keep protesting even at the cost of his career: "He just put his name next to Muhammad Ali. Would you rather be playing football, getting your head dinged in, or would you rather be an iconic figure for the rest of your life?"
June 16, 2018 — Jay-Z Goes on Record
On "Apeshit," the first single off Jay-Z and Beyonce’s album Everything Is Love. Jay-Z raps: "I said no to the Super Bowl: you need me, I don't need you. Every night we in the endzone, tell the NFL we in stadiums too."
December 2018 — Super Bowl Shuffle
Variety reports that Jay-Z tried talking Travis Scott out of performing at Pepsi’s pre-Super Bowl concert on February 1, 2019, two days prior to Super Bowl LIII.
In the end, Scott did perform the headlining gig at Georgia Freight Depot in downtown Atlanta and Maroon 5 headlined the Super Bowl Halftime Show at Mercedes-Benz Stadium; Rihanna and Cardi B both reportedly turned down the gig to show support for the former quarterback.
February 15, 2019 — The Settlement
It’s announced that Kaepernick has reached a confidential settlement with the NFL resolving his NFL collusion grievance. Contrary to later claims, no non-disparagement clause was included. It’s later reported that Kaepernick received less than $10 million from the settlement.
August 13, 2019 — The Turn
On the eve of the third anniversary of Kaepernick’s protest, Roc Nation announces a partnership with the NFL on entertainment (including Super Bowl halftime curation) and the "Inspire Change" initiative. During a press conference announcing the partnership, Jay-Z says, "I think we've moved past kneeling. I think it's time for actionable items... This is the next phase."
Backlash is immediate; critics say Jay took the NFL's money while Kaepernick remained blacklisted. Kaepernick later says he learned of the deal only after contracts were signed. Afterwards, Kaepernick’s attorney Mark Geragos tells ABC that the Roc Nation deal “crosses the intellectual picket line.”
August 30, 2019 — The Subtweet
Kaepernick posts a highlighted passage from Robert L. Allen’s Black Awakening in Capitalist America on Twitter that is widely seen as Kaep subbing Jay-Z.
November 16, 2019 — The Workout
Jay-Z reportedly pressures the NFL into arranging a showcase workout for Kaepernick, who then relocated it at the last-minute over a disputed liability waiver and lack of media access; only 8 of 32 teams' reps follow him to the new site. Sources tell TMZ/SI that Jay-Z was "disappointed," feeling Kaepernick "turned a legitimate workout into a publicity stunt." Roc Nation publicly denied Jay-Z said this.
February 2020 — Jay-Z Plays Defense
While defending the NFL deal, Jay-Z tells the New York Times, "No one is saying he hasn't been done wrong. He was done wrong... but it was three years ago and someone needs to say, 'What do we do now — because people are still dying?'"
July 2026 — The Yankee Stadium Freestyle
During a three-night residency at Yankee Stadium marking Reasonable Doubt's 30th anniversary, Jay-Z addresses backlash over a new Target partnership by naming Kaepernick directly: "They running outta characters, had to bring back up Kaep again / 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."
TMZ notes no such clause existed in Kaepernick's actual settlement. Kaepernick's wife, Nessa, fires back on Instagram, accusing Jay-Z of disrespecting Colin "first, again."
September 15, 2026 — Kaepernick Responds
Kaepernick releases his memoir, The Perilous Fight. While promoting the book, Kaepernick tells NBC News that Jay-Z's comments reveal a "guilty conscience": "The backlash that he received for partnering with the NFL... was a major problem for him, so much so that he's still bringing it up in 2026."
In a companion NPR interview, he says he was "disappointed" by the partnership and accuses Roc Nation of trying to plant unfavorable stories about him years earlier.
