Shady Sam

Shady Sam is a merchant who sells stealth oriented wares. He is a good source of buyable lockpicks before the fences become available in the Thieves Guild. He has 30 lockpicks to sell at all times, as well as various poisons and potions, and also is one of three traders to sell Skooma, the other being Nordinor and Ri'saad. Despite his shady nature, he will not buy stolen goods. He is available at all times of the day, every day. You cannot play the persuasion game with Shady Sam however, his mercantile skill is only 51. He has 400 gold available to barter with, although you could invest in his store. He carries a leveled shortsword.

Finding Shady Sam
Shady Sam isn't hard to find, however at the sight of any law enforcement, he will flee. He stays along the Imperial City walls. To find him, start outside Imperial City and move clockwise along the city wall through the Chestnut Handy Stables. He should not be far from view, to the north, of the stables.