Once the Player has gained access to the back room of the Arena, Daoshen will offer him/her a side-quest to pay Sweet Poison Lyn 500 silver so that he may take higher bets. He promises to reimburse the Player once they return.
Open Palm 1: Pay Sweet Poison Lynn the money and return to Daoshen. Accept the reimbursment.
Open Palm 2: Pay Sweet Poison Lynn the money and return to Daoshen. Refuse the reimbursment and instead the Player will receive a Superior Warrior Gem.
Closed Fist: Pass a conversation check with Daoshen so that he will give the Player the 500 silver outright. Then head to Sweet Poison Lynn and tell her that you won the money in one roll. She will then shut down his operation, and the player can keep the silver. However, this means you can't use Daoshen's gambling services anymore.
Also, winning a total of 5000 silver from Daoshen will cause him to decline you from gambling anymore.
By winning against Daoshen 20 times in a row, Daoshen will explode.
Gambler Daoshen is voiced by Gustavo Rex