Smiling Jack

Smiling Jack is a Raider trader in the Bazaar side of Evergreen Mills in the Capital Wasteland. He never smiles.

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 (verify?). 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.

Another good way to profit from Jack, if you are going to kill him, is to carry valuable items which are in poor condition with you, then have Jack repair them all, he will charge you credits as usual, but since you're in a zero cost situation it doesn't matter. Doing this will essentially repair the items for free, which can add up quickly if you are carrying things such as an AEP7 Laser Pistol, a Minigun, a Missile Launcher, or any of the other items which you would normally find in poor condition, but become highly valuable after a little repair.

A good way to get an impressive amount of supplies from Smiling Jack is to dump your belongings onto a killed Raider corpse (these stay around for a very long time and are safe repositories). Then with an empty inventory, repeatedly search around the Bazaar, gathering up any and all items (no matter how useless) that are laying about in the Bazaar area. There are countless small 1- or 0.5-cap useless junk items laying nearby. Collect all of these and trade them back to him for a substantial profit. Patient collectors can essentially sell the entire Bazaar to Smiling Jack and he will gladly buy it in exchange for caps.

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.


 * Option 5: Sometimes The Terrible Shotgun will be by Smiling Jack on a shelf, and can be easily taken by carrying it (via the hold button) over to a place where Jack cant see you, then "stealing" it. this results in a small karma loss for stealing


 * Option 6: Using the Mesmetron, you can mez Jack, which will cause your companion to attack him, no karma loss will occur.

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

Behind the scenes
Smiling Jack is most likely a reference to the FPS/RPG PC game, Vampire The Masquerade: Bloodlines. In the game there is a character apart of the Anarch faction named Smiling Jack who serves as the tutorial of the game and appears later in the game for advice and backstory on the clans in the game. However besides their namesake, This Smiling Jack and the Fallout 3 Smiling Jack have nothing in common.