|Primary Skills||Alchemy, Enchanting, Smithing, Archery, Light Armor, One-handed, Sneak, Speech|
He wears a set of hide armor with a matching helmet, pair of boots, and bracers. He has two weapons in his possesion: one a leveled mace which can be up to Daedric in quality, the other an iron dagger.
Deep-In-His-Cups has some unfinished business with you about the night of your drinking quest. Apparently you and Sam dared him 10,000 septims to sneak into a bandit camp and steal a hat. He claims you sent him to the camp to die and urges you to pay the 10,000 gold. Persuasion, if successful, will get him to lower the debt at 750 gold. You can then either pay up, or decline and make him hostile towards you. If you pay him (either 750 or 10,000 septims), Deep-In-His-Cups gives you the 1 septim hat, then leaves for Black Marsh.
 Related Quests
- No matter how you opt to deal with Deep-In-His-Cups, he will continue to randomly spawn every once in a while, and make the same demands as before. To avoid paying large amounts of money over time, your best option is to kill him every time you encounter him.
- This bug is fixed by version 1.2.4 of the Unofficial Skyrim Patch.
- If you attack him and then yield, he won't demand the money again, making this an alternate way to get out of paying besides killing him.