Deep-In-His-Cups

Deep-In-His-Cups is an Argonian who approaches the Dragonborn, after completing the "A Night to Remember" quest.

Interactions
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.