Technically, wouldn't this always be a win-lose situation? C'mon man, go for it - Bet ISU on the over and when it happens it will be glorious. If it doesn't, there's always CF for venting sessions and group therapy.
I was about to say the same thing. The four options are:
Win/win - Bet over, win over
Win/lose - Bet under, win under
Win/lose - Bet under, win over
Lose/lose - Bet over, win under
So he is really taking the win/lose option to remove the risk, but decrease the reward. Not that anyone cares.