Chris isn't average compared to the others - in a lot of ways he is much better.But to address your concerns, the reason DT feels so strongly about him and his success is because Chris has already PROVEN himself. He is also still VERY young and has tons of time to go beyond that.
He is already a Real Estate millionare...at this age, imagine where he will be in 5-10 years if he keeps his current success up. He is WAY ahead of all the others...because his team got edged out 7 times by the others doesn't mean he is bad/unsuccessful - he has obviously proven that isn't true.