I lost my luggage at an airport once. I sued the airline, but I lost the case...
Lost Luggage, Lost Case
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Explanation
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Explain Bear
Alright, listen up, buttercup. This dude lost his luggage and then lost his lawsuit against the airline. Get it? "Lost the case" has two meanings. You know, like when you lose your car keys AND you lose a court case, which I bet you're really good at.