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 (Note that it will NOT have the full amount of ammo 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.

The Terrible Shotgun
There are also a number of ways to get The Terrible Shotgun without killing Smiling Jack. To do this, you must first leave any NPC companions outside of the bazaar, as they will attack Jack on sight (See Note below). Then, use either of the following:


 * Option 1: Using the Sneak skill, steal Smiling Jack's shotgun ammunition and head through the exit. Save and load the game.  When you re-enter the bazaar, the shotgun should now appear in Smiling Jack's inventory.  Happy stealing.


 * Option 2: As in Option 1, steal Smiling Jack's ammunition using the Sneak skill. Then place a melee weapon on his person (there are multiple baseball bats and knives in the bazaar).  Provoke him with one punch and then put away your hands.  He will become non-hostile once more, with the shotgun no longer equipped.  The shotgun can then be stolen from his inventory.


 * Option 3: Provoke Jack with a quick punch, which will cause him to draw his weapon. Then, using V.A.T.S., target the shotgun until it breaks and is dropped.  Pick up the shotgun and run for the exit.  The Shotgun is easily repaired using combat shotguns dropped by nearby Raiders.  Smiling Jack may stop being hostile if you save and load the game.

Note: It is not necessary to leave any NPC characters outside of the bazaar. I had Charon, Dogmeat, and Sidney (from Stealing Independence) all with me and nobody attacked Smiling Jack, as he was shown as a "green" or non-hostile character. I did however, kill him anyway for all the loot.