So this question came about from fantasy football, but has turned into a statistics question and I'm deeply curious as to why my intuition is massively incorrect here.

So the total pot is $\$1000$ and I have a $58\%$ chance of winning the game. So, assuming "winner takes all" over say $100$ games, the expected outcome would be that I get $\$58,000$ and my opponent gets $\$42,000$, obviously.

Now, what if, before the game, my opponent and I agree to split the pot up to minimize some risk and ensure we both make a bit of cash. Intuitively, the split that makes the most sense is $58/42$ - winner would get $\$580$, loser would get $\$420$. Any more even (say $50/50$) seems like it would be unfair to me, because I have a $58\%$ chance of winning but only would get $\$500$. Any further apart, I would assume, would be unfair to my opponent due to the same logic.

But, when I do the math on a $58/42$ split, it seems *massively* unfavorable to me. Over $100$ games, I would get ($58$ wins \* $\$580$ per win) + ($42$ losses \* $\$420$ per loss) = $\$51,280$. I would expect this number to also be $\$58,000$, but clearly I am wrong.

1. Where does my reasoning go wrong here?
2. Is there a split that would be fair to both sides?