He demands 10,000 , telling the Dragonborn that during their night of binge drinking, Sam Guevenne and the Dragonborn dared him to enter a Bandit Camp and steal a hat, for which he would be paid 10,000 .
To resolve the issue, the Dragonborn can either pay the 10,000, talk him down to 750 (with Speech), intimidate him, or simply admit to not having the money (after which he will turn hostile and attack for allegedly sending him to the Bandit Camp to die).
The hat itself—which can be received by paying, pickpocketing or looting him—is worth 1 .
- Any gold paid to him will be available in his inventory for looting or pickpocketing.
- His name, Deep-In-His-Cups, points to his tendency to drink heavily, which is why he is involved in the debauchery quest.
- If the Dragonborn claims to not have the money for him, and he becomes hostile, sheathing any drawn weapon can cause him to become neutral and walk away, saying "you are not worth it." (Tested after speech check on and )
- He is similar to the Madwoman and Sigar in that they are all random encounters which occur some time after completing a Daedric quest.
- It is possible to encounter him more than once, even after he becomes hostile and is killed.
- When followed from his initial encounter (if protected and prevented from death along the way) he will become stuck in a loop between Steamcrag Camp & Narzulbur.
- Sometimes he will not speak and attack the player.
- He will occasionally respawn around 5 minutes after being killed and attack the player again. He does not respawn a third time.