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海千山千 (umisenyamasen) Japanese meaning | Kotomora
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じ
家か
だ
。
He is a crafty, experienced politician.
He's a sly old fox, so be careful when negotiating or you'll be tricked.
Related words 老ろう 獪かい 老獪 also means 'cunning' or 'crafty', but emphasizes slyness and wiliness, often with a more negative connotation. 海千山千 focuses on experience and worldliness leading to shrewdness.
世よ 慣な れる 世慣れる means 'to become worldly-wise' or 'sophisticated', but as a verb it describes the process or state of being accustomed to society, without the strong implication of craftiness.
Etymology From the legend that a snake living a thousand years in the sea and another thousand in the mountains becomes a dragon. The immense experience implied by 海千山千 gave the expression its sense of worldly cunning.