Shady Sam is a merchant character in The Elder Scrolls IV: Oblivion and Oblivion Remastered, known for selling suspicious and illicit goods such as lockpicks, skooma (a drug), and various poisons. He is located outside the walls of the northwestern part of the Imperial City, near the Chestnut Handy Stables and close to the Elven Garden District. Players can find him by fast traveling to Chestnut Handy Stables and then following the city wall northward until they spot him in an alcove or corner. Shady Sam does not have a storefront, and he trades discreetly by conversation. He is available day and night but will flee if guards approach. His inventory includes 30 lockpicks, skooma, several types of poisons, and potions to cure ailments. Sam's prices are fixed as he doesn't allow persuasion or bribery to improve his disposition toward the player. This makes Shady Sam one of the best early-game sources for acquiring bulk lockpicks and other questionable items, especially before unlocking the quest item called the Skeleton Key, which allows indefinite lockpicking without consuming lockpicks.
If Shady Sam is temporarily missing, it may be due to a glitch or his fleeing from guards, and waiting or revisiting the location often resolves this.
In summary, Shady Sam is a key merchant for players seeking lockpicks and illicit goods early in the game near the Imperial City walls.