Booted

Booted is a side quest in Fallout: New Vegas.

Detailed walkthrough
During the Courier's visit in Nipton, they will notice that something isn't right. When they first enter the town they will meet Oliver Swanick, who seems to be over-excited about winning "the lottery" runs up and keeps repeating that he has won. Going further into the town, the Legion have taken over the town and killed almost everyone. While searching through the town, the Courier will find a man called Boxcars in the General Store.

Boxcars reacts to the Courier in different ways, depending on their reputation with the Powder Gangers. If it is a positive reputation, he will ease up recognizing them and says that he needs some pain relief. If the Courier has a neutral reputation, he thinks they're going to kill him. If the Courier has attained a vilified reputation he exclaims about how down on his luck he is, because after the preceding events, the Powder Ganger's "Grim fucking Reaper" had just showed up. His legs are crippled by the Legion and tells the Courier 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 the Courier that some of the Powder Gangers were enslaved by the Legion and headed east. He mentions that his legs are in a lot of pain and he needs Med-X. The Courier then has the option to spare some for him (a choice of up to five doses).

Locate the enslaved Powder Gang members at the Legion raid camp. They are tied up around a campfire being watched by legionaries. Upon freeing the slaves, the legionaries become hostile and will attack if the Courier does not have a positive reputation with Caesar's Legion. It's also possible to untie the slaves while sneaking or wearing Legion faction armor, resulting in the the guards remaining friendly. Freeing the Powder Ganger slaves result in a positive increase in reputation with them with no effect on reputation with the Legion (but, as always, killing the legionaries while detected will reduce one's reputation with the Legion). Once the slaves are freed, the quest is completed.

Behind the scenes

 * "Booted" is also the name of a No. 1 1952 song by Roscoe Gordon.

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 you will be able to untie them.
 * 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 dialogue 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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