Smiling Jack

Smiling Jack is a Raider trader in the Bazaar side of Evergreen Mills in the Capital Wasteland.

Background
Smiling Jack never smiles. Alongside Jericho and Lug-Nut he is possibly the only friendly Raider.

After you get past numerous raiders, you'll find him in one market-like corner. He is usually not aggressive towards you, so you can trade with him. But he might steal some things from you, so pay attention, which he will then in turn sell them back to you. (verified on 360).

The Terrible Shotgun
Check this article for tips on obtaining Smiling Jack's unique shotgun.

Bugs

 * Sometimes you will not be able to loot Smiling Jack after killing him. (confirmed PS3)

Behind the scenes
The character may be named for the classic mustached comic strip character, pilot Smilin' Jack.