Smiling Jack

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

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. 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 to karma. If you have the Lawbringer Perk, you can take his finger and sell it for caps and good karma.

There is also a way to get Jack's shotgun without killing him. First, leave any NPC companions outside Evergreen Mills, as he will kill Smiling Jack on sight. Then, provoke Jack with a quick punch, which will cause him to draw his weapon. All you have to do is target his weapon continuously with an accurate weapon until it breaks and he drops it. Pick up the shotgun and run for the door. Now you have a broken, easily repairable Terrible Shotgun. [Discovered By: Legacyslayer (PS3)] He may stop being hostile if you save and load the game.

Yet another way is to steal his shotgun ammunition, leave, save and load the game. The shotgun should now appear in his inventory. Happy stealing.

There is a third way, which includes stealing the ammunition, then placing another weapon on his person, like the knife or bat that is sitting on the self next to were he stands. Then, provoke him with one punch and hold reload to put away your hands and he will be non hostile and not have the shotgun weapon equiped, and it will be available via stealing. This method allows you to still use him as a merchant and get the shotgun off him.