Definition
To lose all of one's money; to go broke; to undergo financial ruin or disaster.
In Context
- "Since nearly losing his shirt in a business deal a few years back, he investigates new opportunities more cautiously."
- "Generosity indeed, but how difficult will it be for some penitent punters to drop a coin in the "sin box" if they happen to have already lost their shirt on a bet placed with Paddy Power?"