He cannot relate to players. Period.
Unless they are people that serve him and his interests, he doesn't care.
There is a big real fucking big reason why he sucks up to Romo, Witten and others. They are insurance.
When they are gone, he has dick.
He can't relate to most players. He's not going to talk to a guy with a hard upbringing and be able to relate, he can't speak to today's NFL athlete.
They are chess pawns to get him along.
That is just not how today's NFL works.
He really needs to go to college. That's where he might actually win something.