uesp:TES Memory: Deep-In-His-Cups constantly requesting you give him 10,000 gold. He claims he was p
uesp:TES Memory: Deep-In-His-Cups constantly requesting you give him 10,000 gold. He claims he was part of your group during Sanguine’s night adventuring with you, and you bet him 10,000 gold to steal a hat, which he presents to you in return for his gold. However you choose to resolve this scenario, his random encounter is not set to ever end, even if you chose to kill him. A new Deep-In-His-Cups will appear and request more money, indefinitely. -- source link