For purposes of Help Me Out Here, "winning" means beating the monster's combat strength. The Item you take must raise your combat strength enough to beat the monster's (or, as with the Kneepads, immediately lead to that situation). You cannot use Help Me Out Here if you are already winning, you cannot use it to take an Item that isn't strong enough to put you over the monsters, and you cannot use it to take an Item that doesn't change your combat strength.