Richard looked at Dean with eyes like daggers, it was almost like he wanted to kill him with his eyes.
Dean couldn't care less about what he thought. He knew Richard was feeling depressed at the moment, but it was not his concern. All he wanted to do at the moment was to humiliate Richard as much as he could.
He couldn't kill the other party, so humiliation was the next best thing to do. Even though the original bet was mainly based on humiliation, he knew the City Lord wouldn't agree to it, so he wanted to take Richard's reward as the price for his victory.
"Don't get cocky, you're only having the upper hand because I underestimated you, and you hid your strength." Richard said coldly.