All these wrestlers are trying to find out who is Number One not Number Two. If Jake is going to win state he has to beat Kendrick. Vice versa for Kendrick.
There could be advantages to meeting a tough opponent on the first day. He may still be suffering from cutting weight, he will have had more matches, you don't have the added pressure and hoopla of a finals match, etc... I think wrestlers in the finals tend to wrestle conservative. If you have to face a tough oppenent then you might be looser and ready to let it all hang out in the quarters than in the finals.