Santiago is a smooth-talking con artist living in Freeside. He affects a Spanish accent to get out of paying for drinks. Thanks to his dishonest ways, he owes Francine Garret 212 caps and has no intention of paying them back before being confronted by the Courier in the side quest Debt Collector.
After Wang Dang Atomic Tango has been completed, the Courier can have sex with him for 25 caps.
There is a dialog option where the Courier can ask for a discount to Mick & Ralph's for 50 caps (25 caps with a Barter or Speech check). He will instruct one to tell Mick or Ralph the word "extravaganza." When this is done, however, they will tell the Courier that he or she has been set up since Mick and Ralph's doesn't do discounts. There will be no dialogue option to talk about this once the Courier returns to Santiago. However, the option will appear when the Courier comes to recruit him for the Garret twins.
Intimidating him will cause him to pay the Courier 256 caps.
If the Courier kills Santiago, they will find 25 caps on his body and they will neither gain bad Karma nor infamy in Freeside even after finishing Wang Dang Atomic Tango.
pcps3xbox360 Recruiting Old Ben to satisfy the "Suave Talker" requirement of the quest Wang Dang Atomic Tango will make it impossible to collect the debt from Santiago through dialogue. Attempting to collect the debt will simply result in a selection of dialogue options where the Courier has no choice but to pay Santiago for his bogus discount password to Mick & Ralph's. [verified]