Dry cleaning is weekly ritual for many. The customer comes into the store with a bag of his or her clothes, drops it off, and picks up last week’s drop-off. Somehow, via a system of tags, the dry cleaner not only launders or alters your clothing, but also manages to not lose your parcels in the process. Well, usually, at least. Sometimes, dry cleaners make mistakes.

And sometimes, customers sue — asking for $54 million in damages for a misplaced pair of pants.

The problem began in May of 2005, when a Washington, D.C. administrative court judge named Roy Pearson dropped off a pair of grey slacks at a dry cleaner named Custom Cleaners, asking for about $10 in alterations. Signage at the dry cleaners promised “same day service” and “satisfaction guaranteed,” as signage often does, but in this case, something went wrong. Custom Cleaners accidentally sent the pants to another dry cleaner, delaying the trousers’ return to their owner by a few days. Ultimately, Custom returned the pants to Pearson — maybe.

Pearson, despite the fact that the tags and receipts matched the pants returned, claimed that these slacks weren’t the ones he dropped off. Pearson demanded that Custom reimburse him for the price of the pants they allegedly lost, and further claimed that the pants retailed for $1,000. Custom, insistent that they returned the right pair of pants and that, in any event, believing $1,000 in compensation to be ludicrous, refused Pearson’s demand. Pearson sued.

Pearson’s claims, though, weren’t limited to the retail price of his almost-certainly-not-lost pants. He argued that the signage in Custom’s windows — those promising satisfaction and same day service — constituted something legally binding, and by failing to deliver his pair of pants in a timely fashion (and in his view, at all), Custom was in violation of their promise. Pearson piled on the claims, as outlined by the Washington Post: $1,000 for new pants, of course, but also; $15,000 to rent a car each weekend so he could travel to an acceptable dry cleaners; $500,000 in attorneys fees; $2 million for his mental distress and discomfort; and tens of millions of dollars more to set up a fund to help similarly aggrieved customers of small businesses file similarly ridiculous lawsuits. In total, Pearson demanded $67 million (which he’d later reduce to $54 million). The owners of Custom Cleaners, Soo Chung, Jin Nam Chung, and Ki Y. Chung, offered to settle (rather than incur massive legal fees themselves, probably), agreeing to pay $3,000, then $4,800, and finally $12,000. But Pearson declined all three offers, electing to pursue his legal claims in court.

And he wasn’t joking. On the contrary, Pearson took the matter very seriously — and very personally. At trial, Pearson’s emotions got the better of him, as the Washington Post explained in another article on the case:

Pearson spent two hours telling his own story, but as he came to the part about when Soo Chung finally told him she had found the missing pants, the tale of the $10.50 alteration that went awry proved to be too much. “These are not my pants,” Pearson recalled telling Chung when she handed him a pair of gray pants with cuffs. “I have in my adult life, with one exception, never worn pants with cuffs.” “And she said, ‘These are your pants.’ ” Pearson paused. He struggled to breathe deeply. He could not continue. Pearson blurted a request for a break, stood up, turned around and walked out of the courtroom, tears dripping from his full and reddened eyes. When he returned, he called that moment when Chung offered him the wrong pants “a Twilight Zone experience,” and again, he welled up and had to halt the proceedings. Pearson wanted to submit the remainder of his testimony in writing, but Judge Bartnoff wouldn’t hear of it.

Judge Bartnoff found in favor of the defendants. But that wasn’t the worst news for Mr. Pearson. Likely in response to the pants suit, D.C.’s Commission on Selection and Tenure of Administrative Law Judges declined to reappoint him to the ten-year extension to his term — an extension which, in typical cases, is pro forma. Pearson didn’t take this idly, of course — he sued the city, claiming he was unlawfully terminated. He lost that suit, too, but at least he didn’t have to give up a pair of pants as well.

Bonus Fact : In 1938, a kindergarten teacher appeared in an L.A. court to testify as a witness in a burglary case. The teacher ended up in jail — because she was wearing pants. According to the L.A. Times, the judge sent her home when she first came to court, instructing her to “return tomorrow in accepted dress” — that is, a skirt. She came back the next day wearing pants yet again and was sentenced to five days in jail for contempt of court. (An appeals court reversed the order.)

From the Archives : A Boy Named Sue: The man who filed so many lawsuits that he earned himself a place in the record books… and then sued the record book. Also, The President’s Pants, just because it’s about pants.

Take the Quiz : Pick the cartoon characters which typically don’t wear pants.