|“||Walk away or the girl dies.||”|
in The demon to Sam Winchester
This unnamed Crossroad Demon was killed by Sam Winchester while he was soulless.
For reasons unclear, this demon encountered Sam while he was hanging out with Robin, and promptly took the latter hostage. Unfortunately, this did not affect Sam, as he felt no sympathy for anyone but himself, since he lacked a soul.
Despite the demon's warnings, Sam shot and killed Robin, so the demon would have no leverage. The demon stared at Sam in shock, before being killed by Sam too.
After regaining his soul, Sam would not remember this incident, but after his wall collapsed, a manifestation of Robin would help him remember the day he killed her and promise he would suffer for it.