Re: right line of thinking here???
he needs to win 1 all in only, you need around 3 double ups to take him out. Assuming evenly matched, its 50% chance that you will double up or go broke each time. Roughly 1 in 8 times you will accomplish to win 3 in a row undefeated.
Same happens on a tournament final HU, if you have 1 million chips vs 10 million of your opponent, you are not 50% to win, even if you are exactly as good/bad as him.
Stacksize does matter
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