Booted

Booted is a side quest in Fallout: New Vegas.

Detailed walkthrough
During your visit in Nipton, you notice that something isn't right. When you first enter the town, a Powder ganger who seems to be over-excited about winning "The Lottery" runs into you and keeps repeating that he has won. When you go further into the Town, the Legion have taken over the town and killed almost everyone. While searching through the town, you find a man called Boxcars in the general store.

Boxcars reacts to the player in different ways, depending on their reputation with the Powder Gangers. If you have a neutral reputation, he thinks you're going to kill him. If you have vilified, reputation he exclaims about how down on his luck he is, because after the following events, the Powder Ganger's "Grim fucking Reaper" had just showed up. His legs are crippled by the Legion and tells you about the lottery that the legion had played with the town of Nipton. The mayor of Nipton had the lottery ticket to be burned in a pile of tires. Boxcars was lucky enough to be left alive but they smashed his legs, and he is now crippled. He explains to you that some of the Powder Gang were enslaved by the legion and headed east. He mentions that his legs are in much pain and needs Med-X. You then have the option to spare some for him (You get a choice of up to five doses).

Once you locate the Enslaved Powder Gang members at the Legion Raid Camp. There are numerous ways to free the slaves in this camp.

There is no Negative Karma for killing the slaves after the quest is completed. Note that freeing the Powder Ganger slaves usually results in a positive increase in rep with them with no effect on your reputation with the legion, unless you kill them.

Alternatively, If you see no faction standing at all in your Pip-Boy 3000 with the Legion, then they may turn hostile once a Powder Ganger is untied. As mentioned above, you will still be able to kill the freed prisoners without a penalty to your Karma. A Stealth Boy can facilitate the infiltration of the camp.

Bugs

 * Sometimes the player will see the Powder Gangers up and walking freely, they will flee (although not far) if you get into combat with the legions. After you defeat the legions, the Powder Gangers will keep walking around, when you try and "talk" to them, you will get an option to untie him or leave him tied regardless of them walking around freely.
 * Sometimes after you kill the Legion Guards, you can't untie the Powder Gangers, just wait and it should be fine.
 * Rarely, a Legion Guard may be tied up and the prisoner standing next to him. Talking to the guard makes him speak as usual. You still have the option to untie the prisoner standing next to the guard.
 * It is probably wise to leave ED-E parked a bit over the hill if it is with you when you do this quest. ED-E doesn't really understand the concept "prisoner" and may fail the quest for you by killing both the Powder Gangers before you can get to them and release them. This is more likely if your reputation with the Powder gangers is Vilified.
 * Rarely, if you untie one of the Power Gangers a Legion Guard will take his place sitting on the ground. Talking to the guard offers the same dialog options as when he's on duty.
 * When you reach the powder gangers they will sometimes appear dead but still be tied up.
 * Sometimes after freeing the powder gangers, they will roam around freely, and after you kill all the Legion, they will kneel back onto the ground and become tied up again. This time, however, you are unable to untie them, though the quest is finished.

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