I'm going to tread lightly, because I know you have a personal relationship here.
But the answer is simple -- mediocre recruiter, no experience as a head coach, no proven track record, poor teacher of the game.
The only [and literally, I mean the ONLY] thing weighing in his favor vs. external candidates who are more qualified is that he's got ties to the program. And as far as evaluative criteria go, that should be pretty far down the list in terms of prioritization.
And it will be, when JW evaluates candidates. Do I think Red will make a short list of 4-5 candidates? Absolutely. Will he stack up against external candidates with head coaching success? Not even close.