Dame Dash compares Jay-Z to Batman villain Penguin as he recalls how the rapper derailed his $40M deal with Tommy Hilfiger 

Music mogul and entrepreneur Dame Dash has reignited discussions around his former business partnership with Jay-Z, startlingly comparing the rap icon and the Batman villain Penguin.

On December 21, 2024, during an interview with The Art of Dialogue, Dame Dash reflected on his tumultuous relationship with Roc-A-Fella co-founder Jay-Z. Dash alleged that Jay-Z consistently undermined his business endeavors, citing a specific instance involving a $40 million deal with the American clothing brand Tommy Hilfiger.

"If you could compare him to a character now, I’d say he’s like the Penguin. He’s ruthless like that," Dash said.

According to Batman Wiki, the Penguin, known as Oswald Cobblepot, is a fictional character and one of Batman's most enduring adversaries in DC Comics. The Penguin is a cunning and sophisticated criminal mastermind, often portrayed as a shady nightclub owner and arms dealer with a penchant for high-tech umbrellas that double as weapons.

---

Dame Dash accuses Jay-Z of sabotaging his deals and likens him to Penguin

On Saturday, December 21, 2024, Dame Dash, a prominent New York record executive, made headlines after an interview with The Art of Dialogue. In the discussion, Dash accused Jay-Z of consistently sabotaging his business endeavors, particularly those involving major industry players.

He alleged that Jay-Z disregarded any financial setbacks he personally faced and actively disrupted his attempts to secure lucrative deals, prompting the record executive to call for accountability.

"Unless he’s [messing] my money up, I don’t give a [expletive] what JAY’s doing. But when he’s [messing] with my money, that’s when I be like, You know what? Enough is enough," Dash said.

Dash referenced a 2005 incident tied to Rocawear, the fashion label he co-founded with Jay-Z. He alleged that a $400 million agreement with Tommy Hilfiger was derailed after Hov publicly promoted his S. Carter brand and distanced himself from Rocawear.

"Right before Tommy Hilfiger signs the papers, [JAY-Z] makes an announcement saying he’s not with Rocawear, that he’s only [messing] with S. Carter. Fu**ed the whole [deal] up and I just feel like he did that only because I was gonna make $40 million," Dash added.

Dash claimed this was not an isolated incident, asserting that Jay-Z had a pattern of undermining his efforts to close substantial deals. According to Dash, whenever he was trying to make a big check, Jay-Z made it fall apart.

Dame Dash recently addressed ongoing speculation about his relationship with Jay-Z, noting that he does not actively speak about the Roc-A-Fella co-founder. He expressed frustration with how others continuously ask him about Jay-Z and then criticize him for discussing their past. Dash emphasized to leave him alone.

"They make it like I just volunteered to start talking about [JAY-Z], but people are really asking me questions about him," Dash said.

In 2005, during an interview with WWD, Dame Dash confirmed that he was no longer involved with Rocawear. He revealed that he had sold his 25 percent stake in the company for $30 million.

According to All Hip Hop, Rocawear generated over $700 million in annual retail sales when Jay-Z sold the company to Iconix Brand Group for $204 million in 2007.

Tensions between Dash and Jay-Z reportedly began in 2002 and centered around disputes over vice president positions within Roc-A-Fella Records. However, the situation worsened following the Rocawear incident.

---

Jay-Z has not publicly responded to Dame Dash’s recent comments.