After resting in Umbria and learning through Remi’s “walkie-talkie” that “the Boss” was safely waiting for them in Dis, the party set out for the city. They encountered smoking pits filled with the smoldering undead along the way. Dis was surrounded by a gorge that acted as a moat, and it was only after offering a bribe that the attendants of the drawbridge granted the party admittance.
They found Kaicho at the Wit’s End inn, and he explained that he had business with the governor of the city. They were all short on coin, so he proposed they earn some by taking bets at the colosseum, where criminals were forced to fight to the death daily. They would need a little capital to get started, so Kaicho challenged Remi to a friendly pickpocketing contest. Milo provided a musical distraction, and Remi scored big when he pinched the innkeeper’s purse, which contained the equivalent of 270 gold pieces. Fearing such a large sum would be missed and suspicion would fall on the new arrivals, Kaicho returned the majority of the loot, keeping some for the party and hoping the owner wouldn’t notice the deficit. He did notice, and Kaicho was forced to hand over nearly all of the rest. In the end they pilfered only 10 gold pieces, not enough of a cushion for a safe bookmaking scheme.
Arden was uncomfortable with these disreputable means of fundraising. Still wanting to contribute, she sought means of earning money for the party through honest work. She considered working with the local apothecary to provide a healing service for venereal diseases to the prostitutes and clients of the nearby brothels, but the apothecary was not supportive of this idea.
The party next sought to gather what intelligence they could about the city and its governor. Through a local contact, Mav discovered that the city guards were holding some sort of large creature intended to be unleashed in the arena upon a particularly unlucky group of convicts at the end of the week. The governor would attend this special event to be held in celebration of his birthday. To get closer to the governor, they considered various schemes for entering the fight, most of which involved disturbing the peace and getting arrested. Ragon was particularly interested in entering the fray, but they decided the deadly nature of the contest outweighed the benefits of meeting the governor through such indirect means.
Attempting a direct approach, the party visited the governor’s mansion in search of an audience with him. The guards initially turned them away, but when Kaicho mentioned the name “Alexi”, a mutual acquaintance of Kaicho and the governor, they were ushered in. The governor was as unwelcoming and abrasive as he was arrogant, and his gaudy attire exceeded even the ostentatious decor that covered every square inch of his home. Here Kaicho’s reasons for coming to Dis were clarified: The governor hired him through Alexi to acquire a painting by a famous artist named Till. Kaicho had attempted to dupe him with a forgery instead of delivering the real thing. The governor’s contempt was therefore not unearned, and Kaicho said he was here to apologize and set things right. The governor explained his intention for the piece, which was to “put it on display” in a pisspot after burning it and urinating on the ashes, as he had done for many other Tills; he apparently held a serious grudge against the artist for some reason. Before expelling them from his home, he told the party that they had better find a worthy replacement for his extravagant collection before attempting to leave his town.
Pulling back yet another layer, Kaicho revealed to his associates his true reason for traveling to Dis: to screw over the governor once again. The governor’s desecration of Till’s paintings and use of art for a pretentious display of wealth were anathema to Kaicho’s philosophy of honoring the beauty in art. Kaicho had a scheme, but first he would need the help of the local thieves’ guild.
Kaicho and Mav attempted to locate the thieves’ guild, but they were unsuccessful. In his search, Mav met someone in deep debt to a hobgoblin loan shark named Bohlatus. Ragon discovered a temple to Kord, the god of athletics and sport, which was occupied by bodybuilders and fighters. Milo and Arden tried to learn more about the colosseum. Through several interactions with the citizens, Arden discovered that she was unwelcome in the city, perhaps because of her race as a wood elf.
The confederates ultimately regrouped at the Wit’s End while Remi went out to pickpocket more gold. Outside the colosseum, in a crowded street, the conspicuous tortle attempted to distract some wealthy patrons with a minor illusion of a dog barking. Their body guard noticed him reaching for their employer’s purse and immediately sounded the alarm. Remi conjured magical darkness to cover his escape and dashed away through a stream of people to the brothels where he attempted to hide by renting a room. The price greatly exceeded what he could pay, so he ran outside again and ducked into an alley behind the Wit’s End. Knowing he was perhaps the only tortle in town and was probably seen by many to be fleeing an attempted robbery, he decided to lay low in the shadows for the night.