Shady Sam in Oblivion can be found outside the walls of the Imperial City, near the Chestnut Handy Stables. To locate him, fast travel to the Chestnut Handy Stables and then head northeast along the city wall, moving clockwise around the wall from the stables toward the Elven Gardens District. He is usually found in an alcove or indentation along the wall, dressed in black clothing with a hood. He is present day or night and sells poisons, potions, lockpicks, and skooma. However, if law enforcement or guards approach, Shady Sam will flee and disappear temporarily

. In summary:

• Location: Outside the Imperial City walls, northeast of Chestnut Handy Stables
• How to find: Fast travel to Chestnut Handy Stables, then follow the city wall northeast
• Available anytime (day or night)
• Sells: Lockpicks, poisons, potions, skooma
• Behavior: Flees if guards appear

This is the best-known spot to find Shady Sam and access his unique inventory in Oblivion