Re: should i pop him here?
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I disagree on turn check/raise. I agree with bond on other points but your opponent is likely bluffing or has a better hand so I'd just check/call turn and check/call river.
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At this point I agree with this because he'll tell himself you can't possibly check a 5 three times and think you have some sort of weak pair and try to push you off - this happens more often than him having a weak pair and calling your value bets IMO because obviously it's going in when you're beat.
Preflop and flop ugh... When I do hit flops like this I lead just because no one will actually think you have a 5, I really have no idea now and I assume you're beat which is why you're posting the hand...
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