A master trader and barterer, Jack is a jovial sort, and not just because he has set up shop next to the raider strip club. He mends the raiders' equipment, which keeps him busy and unable to continue modifications on his pride and joy: The Terrible Shotgun.
Despite being a raider, Smiling Jack is not aggressive to the player character (unless provoked). This is because as a trader, he does not care who buys or sells from his store, so long as the caps are there. He holds no loyalty to the raiders he lives with, as he does not turn aggressive even if the player character kills them in his sight. Still, he urges the player character not to let them see him trading with an outsider, likely fearing that the raiders would turn on him if they were caught.
He stays at Evergreen Mills bazaar running a general shop.
Interactions with the player character
|This character is a merchant.||Sells: ammunition, weapons|
|This character can repair items.||Repair cap: 49|
|This character drops a finger upon death (Lawbringer).|
|Apparel||Weapon||Other items||On death|
|Roving trader outfit||The Terrible Shotgun||Smiling Jack vendor key|
Smiling Jack appears only in Fallout 3.
Behind the scenes
Smiling Jack is a reference to Smiling Jack from Vampire: The Masquerade - Bloodlines, a game developed by former Fallout developers Tim Cain and Jason Anderson. Besides sharing the same name and both having a jovial disposition, Smiling Jack warns the player character in Vampire to 'watch out for shotguns' as they are more volatile to vampires than most guns.
Sometimes, it will be impossible to loot Smiling Jack after killing him. [verified]