The Caballero family has long been known in Lys as prominent merchants, but their reputation is considerably less in Westeros. The second son of the family’s head, Tontos made for Westeros as a young man. He was seeking independence from his family, and in doing so established King’s Landing as the western-most port of their trade circuit. For many years he lived as a bachelor when one day a messenger arrived informing that his elder brother, Feo, was sending his daughter Olivia to be fostered with him. The practice is very unusual in Essos but Tontos ultimately consented; it seemed his niece had been behaving wildly and keeping company with criminals. It was in the interest of all Caballeros that embarrassment and scandal be avoided. After her arrival Tontos rarely saw his niece, and when she did appear something of value would always leave his manse(located north of the Hill of Rhaenys) with her!

As Calaila, Dolins, Teddy, and Thaddeus were leaving the Old Witch Tavern in Flea Bottom they found the mouth of the alley blocked by Tontos and his cadre of personal guard. The four backed into the inn and a few moments later came a soft knocking at the door. The innkeep (Bathue) opened the door and pointed to the room Calaila had barricaded herself in as her friends stood in the dining room and watched. Tontos ordered several of his men to knock the door down. Tontos set his men about the work of searching for her and learned that the clever girl had made an escape through a trap door hidden under a mattress in one of the rooms. Tontos’s coughing worsened as the morning went and he ultimately consented to an examination by Maester Thaddeus. The maester diagnosed whooping cough and fixed a draught of milk of the poppy. Tontos slipped into unconsciousness for several hours, uttering “don’t let them leave” to his men in Lyseni just before passing out. Upon awakening he was furious, having been “out” for so long and without his men having found his prey. Tontos set to torturing Bathue for information until Dolins intervened. The two exchanged words and Dolins ultimately revealed (falsely) that Calaila’s home was the Arbor and that she was a scullion serving House Redwyne. Tontos threatened Dolins that if the bard had steered him wrong in that, pain and retribution were in his future.

Tontos was enjoying the bardic festival in the capital’s center square when it suddenly dawned him that one of the performers was the bard Dolins, who had given him false information about the whereabouts of Calaila. Tontos sent two of his guards chasing after the bard but when the mummer threw coin into the air for the crowd the guards were impeded and the man escaped. Unbeknownst to Tontos, Calaila observed this before she slunk away into the crowd.