Re: Intresting proposal
Assuming you are going all-in preflop, your friend is going to get rich.
To win, you have to survive nine consecutive all-ins. A dominated-hand matchup like AK vs KQ is close to a 75% chance; pair over pair is close to 80%. The only time you will do better than that is when you're so lucky as to be dealt a pair AND catch an opponent with a third card of the same rank.
Winning nine 80% shots in a row is a 13.4% chance (6.4:1 against).Nine 75% shots in a row is a 7.5% chance (12.3:1 against.) If you succeed in busting out several of his hands, towards the end you will have a very small selection of opposing cards to choose from and be forced to take some 50% or worse shots. I would say a fair payoff to you for these rules is in the neighborhood of 20:1.
Your friend could give you an even more generous proposition -- "I'll deal you a hand. You choose any two cards you want from the rest of the deck for me to play." -- and I think he'd still be getting the best of it if he only offered you 5:1 to play nine hands in a row.
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