When I first met him he look at my case and told me how many medals I had and that he had 30. Then I went back with 33 medals and he said he has 50. Can you ever beat him in the contest and if so what do you get.
Nope you can't pass him but there will come a time where you and him have all the medals and be tied.So far for me I'm at 68 medals and he has 100.More info to come if he gives you a item.
When you have more than 100 medals you will pass him. At 113 medals he told me that he's been having trouble since getting to 100. Your satisfaction for having beat him after he was so smug earlier is your only reward (he seems quite sad that you have passed him).