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throw one's hat over the windmill

/θɹəʊ wʌnz hæt ˈəʊ.və(ɹ) ðə ˈwɪn(d).mɪl/

Embrace a risky challenge.

“He threw his hat over the windmill and joined the race.”
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throw one's hat over the windmillのイラスト:Embrace a risky challenge.