Apedia

Lose Shirt Lost Money Spiro Betting Frog Jumping Contest

Idiom Lose Your Shirt
Example Spiro lost his shirt betting against me in the frog-jumping contest.
Meaning to lose everything, especially money
Origin This 20th-century phrase refers to a huge loss of money or property because of a bad bet or poorly managed money. If you end up losing your shirt, it means you've lost practically everything. But the idiom started out meaning "to be very angry" and ready to fight.

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