Damon Dash, a towering figure in hip-hop and film circles, finds himself in increasingly hot water. This time, disregarding the courts could cost him more than bad press. Dash’s long-running legal battle has continued in recent weeks in federal court in New York, where a judge is considering sanctions against him and his company, Poppington LLC. Dash has a history of failing to abide by court orders related to a messy and costly dispute with filmmaker Josh Webber.
The issue revolves around a judgment that began at more than $800,000 and has since ballooned to more than $4 million. It’s not simply Chase going unpaid, but the total has been padded by Dash’s repeated refusals in court to comply with orders to reveal his assets, such as film rights and company records.
Dash has been ordered to comply by a firm deadline of April 28, 2025 , or risk facing significant penalties for violating court orders. And if he doesn’t, well, sanctions and perhaps more severe penalties will be coming his way.
Court filings provide a grim picture of what’s next for Dash: Webber’s legal team is pushing for an order to sell and turn over anything linked to Dash’s business ventures and intellectual property. Their mission is straightforward: hunt down and terminate anything of value and finally begin to chip away at the colossal debt.
The whole clash spirals from a 2022 ruling in Dash’s case, in which he was ordered to pay damages for falsely asserting he owned the film Dear Frank. Shenanigans only went up a notch in 2024, when Dash used an appearance on the “Earn Your Leisure” podcast to attack Webber publicly allegations that Webber says led to his losing a $4 million movie deal.
That action led to a defamation suit, which Dash mostly ignored. In March 2025, he was hit with a $4 million default judgment when he skipped court-ordered mediation and did not produce critical documents.
That’s not all. Dash’s money woes have been well-documented. In December 2024, his one-third share in Roc-A-Fella Records was sold at auction, but this was still not enough to settle his debts, which now total more than $823,000. With the music royalties exhausted, creditors consider Dash’s film catalog their next payday.
For Damon Dash, a self-made entrepreneur who used to boast about being untouchable, there’s the sense that the walls are closing in. If it doesn’t do so by April, his next big defeat might not be another court order but the last of his remaining asset left slipping through his fingers.
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