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- Find Jeffrey
- Kill Jeffrey's Guards: 0/4
- Kill Canine
- Kill Molehill
- Defeat Jeffrey
- Slap Jeffrey
- Go Back to Town
- Slap Jeffrey Again (optional)
- Slap Jeffrey one more time (optional)
Jeffrey can be found near Handsome Bridge beyond numerous knights and orcs. Initially guarded by two bodyguards, he first sends four lesser knights to defend him, then follows this by dispatching Canine and Molehill when the first four fall. Canine is a large knight with a shield and a weapon like a fusion of axe with a mace. Molehill fights using a crude sword of gigantic proportions. Both can inflict serious harm if they get close, although neither are exceptionally fast and can be evaded when they begin to initiate a strike.
Jeffrey, by contrast, is a weak opponent, cowering in fear after the first hit. Additional optional objectives to slap him repeatedly appear when he is struck.
- "The night is dark, and full of flatware."
Turn In: Roland
- After the Stuffy Aristocrat spawns, the quest might stop moving, and will be stuck on objective "Go back to town".
- Winter is a Bloody Business holds various references to Game of Thrones:
- The mission name references the words on House Stark in Game of Thrones 'Winter is Coming' and the phrase 'It's a bloody business Bates' which is a reference to Downton Abby.
- Prince Jeffrey is a reference to Joffrey Baratheon.
- Canine is a reference to Joffrey's one-time bodyguard, the Hound, and Molehill represents the Hound's brother, often called the Mountain.
- The act of slapping Jeffrey references several scenes where Joffrey has been disciplined with a slap.
- Jeffrey's throne is fashioned from a collection of weapons in the same manner as the Iron Throne.
- The Stuffy Aristocrat NPC is part of additional referential jokes, apparently referring to the ECHOnet version of Downton Abbey, which is Mordecai's favorite.