Smooth-Talking Criminal

Smooth-Talking Criminal is an unmarked quest

Detailed walkthrough
Talk to Francine Garret of the Atomic Wrangler Casino and ask if she has any work to be done. This starts the side quest Debt Collector.

One of the individuals who has to pay up is Santiago, a smooth talker residing in a squatters camp near Freeside's east gate. He tries to talk his way out it by saying he is a V.I.P. at the casino and offers the Courier a password to get a discount with Mick at Mick & Ralph's. This will cost 50 caps (25 caps with a Barter or Speech check of 40).

Head to Mick & Ralph's to acquire the discount from Mick. However, he will tell the Courier that they do not do discounts. There will be no dialogue option to talk about this once the Courier returns to Santiago.

Return to Santiago to collect his debt.

Behind the scenes
The name of the quest references Michael Jackson's single, Smooth Criminal.