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Meaning

a wily old hand

The cunning of someone who has seen a great deal of the world and knows all its ins and outs; also, such a hardened person.

Example

相手は海千山千の交渉役だから、こちらの手の内は読まれていると思ったほうがいい。

The other side's negotiator is a wily old hand, so assume they can already read our cards.

Origin

From the belief that a snake that has lived a thousand years in the sea and a thousand years in the mountains becomes a dragon. From the Edo period into the Meiji era the longer form umi ni sennen yama ni sennen was usual. Examples of the shortened four-character form umisen yamasen appear from the Taishō era, making it a relatively new expression.

Sources