Back in 2005, a Washington, D.C. administrative law judge named Roy Pearson got into a dispute with his neighborhood dry cleaners over a pair of pants he said weren’t his. Instead of handling it like a normal human being—asking for a replacement, a refund, or just going somewhere else—he sued them for $67 million.

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His argument was that the shop had “Satisfaction Guaranteed” signs posted, and under D.C.’s consumer protection law, he claimed that entitled him to massive damages. So he did the math in the most extreme way possible, counted every sign, every day, added in attorney’s fees (for himself), and somehow landed at $67 million… over pants.

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The dry cleaners were a small, family-run immigrant business. They offered to settle. They offered money. They offered to replace the pants. Pearson refused every time. The lawsuit nearly destroyed them—financially and emotionally—and forced them to shut down stores just to pay legal bills.

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Pearson didn’t win. He lost at trial. He lost on appeal. He lost again. And when his own judicial position came up for renewal, it was over. The commission basically said someone who sues for $67 million over pants doesn’t have the judgment to sit on the bench.

The case became famous—not because it exposed injustice, but because it became the poster child for ridiculous lawsuits. Law school textbooks still talk about it.

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The lesson isn’t that he didn’t have the right to complain. He did. The lesson is that there’s a difference between standing up for yourself and completely losing perspective. What should’ve been a five-minute conversation ended careers, businesses, and peace of mind—all because someone couldn’t let it go.

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Sometimes the problem isn’t the law. It’s the lack of common sense in using it.

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What’s your take? Where do you draw the line between standing up for your rights and letting something go?