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.

You can find the Vault-Tec Bobble-head for Barter in the back room of his shop -- on a shelf behind a workbench.

Smiling Jack is classified as "evil," meaning nothing you do to him will result in Karma loss.

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.
 * Note that despite the fact that ammunition is weightless, and not particularly valuable, Smiling Jack seems to frequently notice when you try to steal his ammo. To ensure that your thievery goes unnoticed, it helps to exchange an equal number of another type of ammunition (he carries no other weapons). Later, when you come back for the shotgun, it can also be replaced with another type of weapon (Tested with Flamer Fuel and a half-repaired Chinese Assault Rifle).


 * 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.


 * Option 4: Walk behind Jack with a high powered single shot weapon like the Blackhawk, using V.A.T.S., target the shotgun, one shot should break it. Put away your weapon which will make him non-hostile again, and sneak behind Jack, and pickpocket the broken gun from his inventory. The Shotgun is easily repaired using combat shotguns dropped by nearby Raiders.

Note: It is not necessary to leave any NPC characters outside of the bazaar.