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I'm not afraid of a gunfight, but I'd rather get back to Red Rock without a few extra holes in me if I can help it.”
A fierce Great Khan who understands the meaning of loyalty, Jessup was part of Benny's entourage that helped the Chairmen leader ambush the Courier outside Goodsprings. Lured in with the promise of caps, Jessup stuck with his fellow Khans and watched closely over Chance, the disturbed Khan plagued by memories of Bitter Springs. After Chance overdosed in the night, Jessup ensured that he'd be given a decent burial, despite Benny's insistence on moving on to ensure they can catch the Courier.
After the ambush, Jessup and the rest of the Khans headed back to Vegas through Novac, around the McCulloughs, due to the events that closed off the western valley to caravans. After an unfortunate run-in with an NCR Army patrol north of the little town, the Khans were forced to hole up in the Boulder City ruins with the wounded McMurphy in tow. To protect against an attack, they captured two of the patrolmen, privates Gilbert and Ackerman, and kept Lieutenant Monroe's men at bay. Rather than face the NCR, Benny disappeared into the night with the Platinum Chip, leaving the Khans without payment to fend for themselves. Since then, Jessup has been trying to come up with a plan that would allow him and his Khans to get back to Red Rock without a few extra holes in them. 
Interactions with the player character
|This character is involved in quests.|
- Boulder City Showdown: Jessup is the Khan leader and the player has to deal with him in order to save the hostages - or get the Khans out safely. If he returns to Red Rock Canyon, it's possible for him to die on the way due to wildlife and Powder Gangers.
- They Went That-a-Way: Reaching Jessup ends the quest, as he gives the player the identity of their would-be killer. Jessup will give the player Benny's lighter if they mention heading to the Strip, insisting that he shove it up Benny's backside for the betrayal he and the Khans suffered.
|Great Khan suit armor|
|Engraved Cigarette Lighter|
Chairmen Job Offer
Drops on death
|No additional items|
- "What the hell? You're that courier Benny wasted back in Goodsprings. You're supposed to be dead."
- Jessup's dialogue may not update when arriving at Red Rock Canyon.
- Stealing the engraved lighter from Jessup will not change his dialogue and the script will add a second one to the player's inventory.
Jessup in the All Roads comic
- The Courier: "What can you tell me about Benny?"
Jessup: "He's one of the Chairmen, big shots who run The Tops casino in New Vegas. A friend from the city contacted me with info on a big job. I should've known that the caps were too good to be true, but there was still no way I could pass up the chance."
- The Courier: "Why did Benny betray you?"
Jessup: "He's a snake, that's why. He owed us the rest of the pay for the job, so maybe he didn't want to pay up."