Daniel's cruelest action
Perhaps the worst thing Daniel ever did was end Chozen's ability to have children. After Chozen recovered his money (Daniel had no rebuttle when Chozen said, "no, my money!") so we have to assume Chozen is correct, Daniel does something absolutely despicable.
While Chozen is in a cool-off and happy state, completely unprepared, Daniel from a low position gets tremendous leverage by pushing his feet off the ground and gets a direct hit to Chozen's family jewels. When Daniel got low blows (from Barnes), his adrenaline would have negated the pain somewhat, however Chozen was certainly not in a flight or fight situation when Daniel landed that cheap shot. It was unnecessary. Chozen was not attacking him, and would have allowed Daniel to leave once the money was recovered. It truely was Chozen's money in that he did not agree to a $600 bet. His uncle Sato forced his hand and he couldn't afford to lose face in front of his home town. It is partially Sato's fault, but Daniel is mainly to blame for hustling Chozen.