[chief_]

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Live Question:
If I think that I can get a good feel for where he's at, with some table banter, should I make it, even if I think that he will likely interpret my banter as strength?

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If table banter will help you assess accurately where you are at, and villain is able to act on his read of strength and only call a river raise here with better hands, you will usually be only folding or calling, but you will know which is better more accurately after you interact with him.

It looks like a close shove and the info you want to get probably "costs" too much to acquire.