Shady Sam is found outside the Imperial City walls, near Chestnut Handy Stables, and he is there at any time of day.

Exact location

  • Fast travel to Chestnut Handy Stables , east of the Imperial City.
  • Go around the back of the stables and start following the city wall.
  • Keep walking along the wall toward the north / northwest side of the Imperial City , in the direction of the Elven Gardens District.
  • You’ll find Shady Sam standing in a little nook/alcove along the outer wall , dressed in black with a hood.

He’s available day or night , with no quest requirement to unlock him—just walk up and talk to start bartering.

TL;DR: Chestnut Handy Stables → go behind them → hug the Imperial City wall toward the northwest/Elven Gardens side until you see a hooded guy in black: that’s Shady Sam.

Information gathered from public forums or data available on the internet and portrayed here.