[Clipper]

Bad Stuff is applied immediately as soon as you roll, so you treat both attempts separately, not rolling both then applying the Bad Stuff.

Now, the question is how to apply the Bad Stuff separately. I'd say that you just do it normally, with the lower level player giving up his stuff when he rolls, including to his partner combatant, but the higher-level player giving nothing away. I could see it being argued that the rule that you can't trade or take Items during combat (and hence while running too) might exclude the high-level combatant from receiving an Item, but the card text seems to override that rule.

Edit: Now that I think about it, I might like to challenge Andrew's ruling above when you are tied for highest. The card mentions that player/s of the highest level take stuff from you. If you are tied with them, they should still be able to take stuff from you, I would think. Yes, if you are the only highest player, then it would fizzle.

If this is correct, it would change my answer above slightly as the other high-level non-combatant would be able to take an Item from the high-level combatant when he fails his Run Away roll.