Dame Dash compares Jay-Z to 'ruthless' Batman villain Penguin as he recalls $40M deal betrayal

Dame Dash recalled how Jay-Z sabotaged a $40 million deal he was about to close with Tommy Hilfiger in the early 2000s
PUBLISHED DEC 31, 2024
Dame Dash reflected on his strained relationship with Jay-Z (James Devaney/GC Images, Timothy Nwachukwu/Getty Images)
Dame Dash reflected on his strained relationship with Jay-Z (James Devaney/GC Images, Timothy Nwachukwu/Getty Images)

LOS ANGELES, CALIFORNIA: There's no love lost between former business partners Dame Dash and Jay-Z after what transpired between the two involving American clothing brand Tommy Hilfiger.

Dash, during an interview with 'The Art of Dialogue', compared Jay-Z to Batman villain Penguin and recalled how the rapper derailed his $40M deal with Tommy Hilfiger, according to Vibe.



 

Dame Dash compares Jay-Z to Batman villain Penguin

During the interview on December 21, Dame Dash reflected on his tumultuous relationship with Jay-Z and alleged that he consistently undermined his business endeavors.

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

ATLANTA, GEORGIA - AUGUST 07: Damon Dash attends the 2022 InvestFest at Georgia World Congress Center on August 07, 2022 in Atlanta, Georgia. (Photo by Paras Griffin/Getty Images)
Damon Dash attends the 2022 InvestFest at Georgia World Congress Center on August 07, 2022, in Atlanta, Georgia (Paras Griffin/Getty Images)

He further alleged that Jay-Z disregarded any financial loss he faced and also disrupted his attempts to lock good deals, making Dash call for accountability, per the outlet.

He said, "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."

He referenced to Rocawear incident, dating back to 2005, which he co-founded with Jay-Z. Dash alleged that a $400 million deal with Tommy Hilfiger was broken after the rapper promoted S Carter brand and stepped away from Rocawear.

LOS ANGELES, CALIFORNIA - OCTOBER 13: Shawn Carter attends the Los Angeles premiere of
Jay-Z attends the Los Angeles premiere of 'The Harder They Fall' at Shrine Auditorium and Expo Hall on October 13, 2021, in Los Angeles (Rich Fury/Getty Images)

Dash added, "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. F****d the whole [deal] up and I just feel like he did that only because I was gonna make $40 million."

Dash sold his stake in Rocawear and walked away with $22.5 million while JAY-Z, on the other hand, sold the clothing brand to Iconix Brand Group in 2007 for $204 million, per the outlet.

Dame Dash expresses frustration with him always talking about JAY-Z unprovoked

Dame Dash also expressed his frustration with the idea that he is always talking about JAY-Z unprovoked. He said, "They make it like I just volunteered to start talking about [JAY-Z], but people are really asking me questions about him."

He added, "If everybody doesn’t want to hear me talk about JAY, why the f**k do people keep asking me questions about him?"



 

Notably, JAY-Z and Dash’s feud has been active for more than two decades and even Steve Stoute spoke about it on 'Club Shay Shay'.

He told Shannon Sharpe back in March 2024, "Dame wouldn’t change. The way he spoke to people, the way he treated people. He was angry. He was angry because he had a strong perspective about his business philosophy. People were becoming less beholden to him."

He also pointed out why the 24-time Grammy winner ultimately distanced himself from Dash. He said, "Jay seen Dame’s ceiling. He wanted more. And everybody wanted more. Dame just had a very particular way of approaching it."

He added, "He’s far from stupid. Very very very smart. Very talented. Ego through the roof. Through the roof! So, there was no working with him. No one wanted to work with him. As much talent as he has, nobody [wants] to work with him."

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