Smiling Jack

Smiling Jack is a Raider trader in the Bazaar side of Evergreen Mills in the Capital Wasteland in 2277.

Background
Smiling Jack never smiles.

Daily schedule
He stays at Evergreen Mills Bazaar selling anything he has to raiders.

Interactions with the player character
After you get past numerous raiders, you'll find him in one market-like corner. He is not aggressive towards you, so you can trade with him. He can repair any your items for payment.

You can kill him with no Karma effect, as he's technically a raider, and he drops The Terrible Shotgun. He also drops a key to his store, which you can also loot with no loss of Karma. Note that it will NOT have the full amount of ammo or stimpaks if you kill him. To get around this, buy it from him first, then you can loot the full amount of caps back. If you have the Lawbringer Perk, you can take his finger and sell it for caps and good Karma.

Appearances
Smiling Jack only appears in Fallout 3.

Bugs

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