Damon Dash Is 'Embarrassed' Former Pal Jay-Z 'Has to Work' at 56 After Rapper Said Dash Is 'Down on His Luck' in Freestyle
Damon Dash Is 'Embarrassed' Former Pal Jay-Z 'Has to Work' at 56 After Rapper Said Dash Is 'Down on His Luck' in Freestyle
Ilana KaplanWed, June 3, 2026 at 7:10 PM UTC
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Damon Dash blasted Jay-Z in a recent interview for his performance at the Roots Picnic
The music executive told The Art of Dialogue on Tuesday, June 2 that he was "embarrassed" for the rapper
Dash's comments come amid his own $25 million debt, which was revealed in September 2025
Damon Dash criticized Jay-Z for his recent — and rare —solo performance.
While speaking with The Art of Dialogueon Tuesday, June 2, the music executive said he was "embarrassed" for the rapper, whom he co-founded Roc-A-Fella Records with in 1994, to be playing the Roots Picnic in Philadelphia on Saturday, May 30.
“And I felt bad because I was like, ‘It must be embarrassing for him to now have to be on that stage, not the same version of himself, and still have to work at that age because he has to,'” Dash, 55, who owes $25 million in debt, said of the 56-year-old rapper. “For him to have to come out 20 years later, I just felt kinda embarrassed for him.”
Damon Dash in December 2018 in Los Angeles; Jay-Z in May 2026 in New York City
Credit: MediaPunch/Shutterstock; TheStewartofNY/Getty
He also made a dig at Jay-Z's afro, which he debuted during the set.
“I couldn’t hear the lyrics because the hairstyle was crazy," Dash continued. "Why would they let him come outside like that. That s--- is funny and there should be jokes for that hairstyle."
Despite his comments, he said, "I still care about Jay. Jay, when you do Yankee Stadium, I need you to get a Caesar, I need you to put the Yankee hat on and do the thing to the side."
Dash added that people "don’t want to see this version" of Jay-Z.
Per Billboard, many believed Hov referenced Dash during his show on Saturday when he rapped: “That Chatty Patty down on his luck again/ N—as teeth is tumblin’ out their mouth and somehow I’m the one who done it, there’s a murder mystery game."
During Jay-Z's freestyle, he also appeared to take aim at Kanye West, Nicki Minaj, Tory Lanez and Drake.
PEOPLE has reached out to representatives for Jay-Z for comment.
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Jay-Z in Philadelphia in May 2026
Credit: Courtesy of Roc Nation
In September 2025, Dash filed for bankruptcy, claiming that he had accumulated more than $25 million in debt and has just over $4,000 to his name, per court documents obtained by PEOPLE.
According to court documents, he filed for Chapter 7 bankruptcy in Florida on Thursday, Sept. 4, listing his total liabilities at $25.3 million,
Dash listed his monthly income as $0, and said he does not own a house, car or any electronics, aside from his $500 cell phone.
According to him, his personal assets, including his phone, two guns, clothes and $100 in cash, are worth $4,350.
Damon Dash in June 2026
Credit: The Art Of Dialogue/YouTube
Per the documents, his domestic support obligations are over $647,000, and he owes the government $19.1 million in taxes and other debts.
He also owes hundreds of thousands to his ex-wife Rachel Roy, with whom he shares daughters Ava, 26, and Tallulah, 18, in addition to Cindy Morales, the mother of his son Lucky, 22, and Linda Williams, mom to his son Boogie, 34.
Dash claimed Kareem Burke, with whom he co-founded Roc-A-Fella, owed him a “possible” but “unknown” sum.
The New York Post reported in November 2024 that the New York state government purchased Dash’s one-third share in Roc-A-Fella at auction for $1 million in an attempt to collect the $9 million tax debt.
At the time, the outlet reported that the entrepreneur was previously listed as the 27th-most tax-delinquent New York resident.
on People
Source: “AOL Entertainment”
