I dont think he's the all knowing one or anything but I doubt he's just locked in a room somewhere slugging redbulls and trying different trade scenarios on his Xbox either.
He's been involved in the league a long time and has plenty of contacts of his own including Rutherford and Karmanos who do have experience and can help him navigate if needed.
I see nothing wrong at this time IMO in giving him the benefit of the doubt and trusting him to get the best deals he can get.