Dean had a smug expression on as he walked off the platform proudly. The battle wasn't as easy as he made it seem, his confidence was what gave him the advantage in the battle.
From the start of the battle, Richard was dumbfounded by Dean's strength, and Dean used that to his advantage, making sure before Richard could recover from it, he defeated him.
It could be said that he was able to win due to Richard's shock.
He didn't forget to take the treasure Richard was rewarded in the competition. Although it was not on the same level as the ones they got, he still wanted to take it. He wanted Richard to suffer, and taking this would humiliate him.
Richard walked to the Dale Family's camp with his head down and his legs shaking. He was brutally injured by Dean's last kick. Dean was a ferocious person and he didn't hold back in that kick.
