I find it hard to believe that you are trying to justify your play as being a good one.
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However, I felt like a fold here would be a waste of a favorable opportunity.
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A $50 raise faces your A8s when the blind is $5. Do you understand what it means when I say it's either a close race or you are a BIG dog? Big dog means you are a 70% or worse underdog. ALL he needs is A9 or a pair larger than 77 and you ARE that big of an underdog. There is virtually NOTHING he could have that makes you anything more than a VERY SLIGHT favorite. The rest of the time, you are going to be in a very close race. This means it is a LOSING call to play here.
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Thus, I felt I could consider any money they put in the pot as dead money if I sacked up and moved on the pot.
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Who is it exactly that put in the dead money here?
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Even if they don't fold (very unlikely): I have position and the opportunity to outplay them for the side pot.
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First off, how big are the stacks? You've already put in $250. How much is left to play for?
Next, let's review the potential side pot situation. When you make a collosally large bet like you did here, you will only be called by a better hand, thus there is NO value whatsoever other than NEGATIVE EV in making such a large bet with such a weak hand.
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Considering the caller money in the pot as dead, I'm really making a mistake here if the all-in guy has aces. If the allin guy has KK or a better ace, the dead money is giving me the right price to call.
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This part baffled me the most. How much dead money do you think you need to take on KK with A8 or a better ace with A8 and have a +EV? You will be break even at best here. Let's look at some sims from twodimes.net...
http://twodimes.net/h/?z=438447
pokenum -h as 8s - kc kh
Holdem Hi: 1712304 enumerated boards
cards win %win lose %lose tie %tie EV
As 8s 548832 32.05 1157419 67.59 6053 0.35 0.322
Kc Kh 1157419 67.59 548832 32.05 6053 0.35 0.678
http://twodimes.net/h/?z=118563
pokenum -h as 8s - ac kh
Holdem Hi: 1712304 enumerated boards
cards win %win lose %lose tie %tie EV
As 8s 488110 28.51 1147813 67.03 76381 4.46 0.307
Ac Kh 1147813 67.03 488110 28.51 76381 4.46 0.693
Notice these don't even consider the other players in the hand, all of whom take more equity away from you.
Sorry to be so harsh, but you are VERY mixed up here and I am trying to help.
al