Re: 10-20 O8, who made bigger mistake?
I would rate your play as a bigger mistake. Assuming you get HU against UTG with your raise, do you think your hand is a favorite? Raising to push others out of the hand makes sense if you have a hand that plays better HU than against many, but KKJ5ds is not that kind of hand IMO.
Calling two cold with A339s is kind of loose, but less bad than your play.
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