Re: Time for an overbet
This looks pretty crappy. Also sounds like you like chasing gutshots, and for this one in particular you may only have had 3 outs.
I guess if you are 100% sure he wouldn't check the turn with 2-pair, trips, flush and would check an ace you could justify it. But as you decribed him why not just make a weak-lead on the river and let him call with his jack, or raise you with his ace?
Against anyone with half a brain this hand is very bad but I hope it worked our for you against this guy.
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