Hackett has no standing upon which to ask tough questions. He never fielded them as a player, and I remember reading one report that he wasn't the most accommodating player out there anyway.
ESPN 700 is the HOTRU. It's not supposed to act as the 60 Minutes of Utah sports. Hackett has zero reporting/journalism experience and probably can't discern between the two. In any event, Tillman shouldn't be forced to field any tough questions before he's played in a game. And anyone who's deserving to field tough questions don't need to be softballed and given them in advance.
You forgot one key stakeholder that needs to be happy -- your advertisers. They rank ahead of all of the other groups you mentioned.