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The phrase "lost his shirt at the track" means that a man gambled so much on the races (horses, dogs, etc) that he spent all his money and had to resort to his clothing for this bets.

Used as an idiom, this phrase means that someone has taken a, perhaps foolish, chance and lost.

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15y ago
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11y ago

He lost his shirt on that deal means he took a big risk that resulted in him losing a lot of money.
It means he lost everything -- the image is of someone who has lost so much that he even lost his clothing.

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