Find and speak with Santiago; ask about his "VIP status."
Pay Santiago 50 capsor pass a 50 Barter skill check to negotiate down to 25 caps.
Speak with Mick at Mick & Ralph's; ask about a special discount.
Return to Santiago; pass a 40 Spech check to intimidate him into paying back 52 caps.
Detailed walkthrough[]
To start the quest, travel to Freeside and enter the Atomic Wrangler Casino. Speak with Francine Garret behind the bar counter immediately to the right; Francine normally tends the bar from 7am to 8pm. Ask her about work needing to be done to trigger the side quest Debt Collector, where Francine sends the Courier to collect a sum of caps from debtors, one of which is known suave talker Santiago.
Santiago can be found at the squatter campsite opposite from Mick & Ralph's, behind the ruined building (where one would find an NCR missionary during G.I. Blues). Asking him about paying his debt to the Garrets will lead to Santiago attempting to use his suave talker skills to weasel out of giving up his caps. Part of his strategy is mentioning that he has "VIP status" in Freeside. If one asks further, he will claim to be so high-class to the point of retaining a discount on services at Mick & Ralph's, which he is willing to "offer" for a sum of 50 caps. Two options are available to either pay the 50 caps or pass a 40 Barter skill check to negotiate the price down to 25 caps. Upon payment, Santiago says the password is "extravaganza." Once his fee is paid, one can then proceed with getting Santiago's debt for Francine; see the associated page for that quest for more details.
Go to Mick & Ralph's near Freeside's east gate. Talking to Mick and trying to use Santiago's discount will cause Mick to trying to reveal that Santiago has lied. Return to Santiago and mention the fake discount. He will try to bluff his way out of the consequences; one can either state scare him with the threat of violence or pass a 40 Speech skill check to intimidate him into paying back his fee at 52 caps.
