Courage abilities only work when the card with that ability is played 1st in the round.
Also, you were thinking of confidence.
Courage: only activates if played first in a round.
Confidence: Activates if your last card won.
Think of it like this.
Courage - Your friend running at a 6ft hench bouncer only being 8stone himself
Confidence - your friend won the fight so obviously you must be able to.
Defeat - apparently not.
Revenge - you know people in high places.