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.

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.