Pearson, an administrative law judge in Washington DC, claims he's owed the money because he devoted more than 1000 hours to represent himself in the battle.
He insists he has been put through "mental suffering, inconvenience and discomfort". And because he does not have a car, he says he'll now have to RENT one just to get his clothes cleaned at another store.
According to court papers, Pearson dropped off his trousers on May 3, 2005. But they were not ready when he returned later.
Aweek later, the cleaners came up with grey trousers they said were Pearson's - but he insisted they were not the ones he dropped off.
This week, DC Superior Court judge Neal Kravitz said: "The court has significant concerns that the plaintiff is acting in bad faith because of the breathtaking magnitude of the expansion he seeks."
Lawyer Chris Manning, representing Custom Cleaners' owners Ki, Jin and Soo Chung, said: "They have been abused in a ghastly way. It's going to cost them tens of thousands to defend this case."
The Chung family insist his trousers are still at the store, waiting to be collected.