Boulder City Showdown

Boulder City Showdown is a side quest

Overview
Jessup is holding 2 NCR troopers, Privates Gilbert and Ackerman, hostage in the Great Khan hideout, inside the Boulder City ruins. Lt. Monroe of the NCR asks the Courier's help in getting them released.

Detailed walkthrough
Speak to Lieutenant Monroe to begin the quest, and walk through the door behind him. From here, the player character has 3 options as to how to proceed:

Option: Free hostages via negotiation

 * Enter the Boulder City ruins and go into the Great Khan hideout.
 * Talk to Jessup.
 * By passing a Speech check (45), the player character can convince Jessup to release the hostages and have the Khans leave peacefully.
 * One can convince Jessup to shoot his way out.
 * One can convince Jessup to release the hostages.
 * By asking Jessup about the Platinum Chip, the player character will complete They Went That-a-Way.
 * Go back and speak with Lieutenant Monroe. He informs the player character he has been given orders to kill the Great Khans, hostages or not.
 * One can talk Monroe into honoring the deal and not killing the Great Khans. This results in the player character gaining fame with the Great Khans and the NCR, receiving good Karma, and an additional 300XP.
 * One can offer to give him 500 caps (or less, with 45 Barter) to let the Khans escape.

''Note: If one engages in hostile action with the Great Khans, the player will still be accepted with both factions. Also, if this option is chosen, Jessup will give the Courier the engraved cigarette lighter which can be given to Swank at The Tops, as evidence that Benny does not have the best interests of the Chairmen in mind.''

Option: Free hostages by killing the Khans

 * One may choose to free the hostages by killing all the Khans in the area.
 * The player character must kill all the Khans in the Ruins, including the two in the Hideout.
 * Release the two NCR hostages in the building next to the Hideout.
 * Return to Lt. Monroe and speak to him.
 * Upon completion, the player character will gain fame with the NCR and infamy with the Great Khans.
 * Note: If one sneaks to the backdoor where the hostages are held and releases them, this will not alert the Great Khans. However, once released, the objective will change to kill the remaining Khans. Once the Khans are killed, the quest will be completed.
 * Note: If instead of killing any Khans, the player character taunts them but allows the NCR troops to do the job, this will not result in any infamy with the Khans.

Option: Killing the NCR troops

 * The player character must kill all the NCR troops in the area, including Lieutenant Monroe. There are about 5 soldiers within the ruins.
 * Once all NCR soldiers are dead, inform Jessup the Khans are free to go.
 * Note: The hostages will remain tied up in the ruins. The player character can either leave them be, free them or kill them. Killing them results in XP and Karma loss, in addition to NCR infamy. The Great Khans will attack the player character if the hostages are engaged, so wait for them to leave the area.
 * Upon completion, the player character will gain fame with the Great Khans.

Quest stages
Negotiation path:

Siding with the Khans:

Siding with the NCR:

Bugs

 * If one goes to New Vegas and circumvent the entire Boulder City main-quest arc, Jessup's only dialogue response will be to say Goodbye, making the quest impossible by diplomatic means. This glitch can be rectified by completing the quest "Oh My Papa".
 * The game may suddenly switch the objective from negotiations to kill all NCR in the area. This somehow will cause the hostages to immediately become hostile and attack you. You will be forced to kill them, initiating negative Karma loss and NCR infamy. However, the other NCR members do not become hostile and the quest can be completed by simply killing Jessup. However, sometimes simply killing Jessup will not fix the bug in which you will need to use commands to set the quest stage to the desired point.
 * If talking to Private Ackerman after freeing him, there will be a slight audio glitch on the "Thanks" in "Thanks for getting me outta there. I owe you one."