I guess the issue i have with this "champion vs winner" issue is the idea that they are mutually exclusive categories. Is someone who wins one championship, and other than that year has a very mediocre career more of a winner than someone like Marty Schottenheimer, who build consistent playoff teams? I guess i don't think it is as easy as to count the number of rings on your finger, especially in team sports.
What I find interesting is the farther along in JFJ's contract limbo JFJ is, the more he makes a change more difficult. Throwing JFJ out now and starting over will be very difficult considering the lack of picks a new regime would have to work with. Sure, Bowman and whoever he hand picks would have a plethora of prospects to trade, but whatever new direction he would like to take the team, progress would be stunted to say the least. What I'm getting at here is JFJ has been insulating himself within the team by making it harder for MLSE to replace him. He isn't accomplishing this feat in the usual way by winning games, but rather forcing the team into limited window of 'win now' that isn't anywhere close to a Cup contender. And do I blame him? Not entirely. The blame must be rooted in the organization that is structured to reward this type of behavior. And to be fair, I have no 'fire him now' urges towards JFJ. I've liked some of his moves, not all, but some. He isn't allowed a full-on rebuild, which isn't a sure thing to begin with, so he rebuilds on the fly and is doing an ok job of it. The core is getting younger; youthful wingers supported by slightly older defenders. He isn't signing vet after over-paid vet. Yet at the same time, he is undermining his scouting staff, undoing one of the organizational pluses he was responsible for. Maybe I am blaming JFJ more than I had realized. Either way, Bowman would be a great addition to the Leafs in that he would get the board out of the hockey side of things. But really, is this the way Bowman handled his previous hirings, denying even the offer of a job? I don't have an answer, but I suspect not.
I have read a couple of things regarding the power structure at Maple Leaf Sports and it is a mess at a level about JFJ which does explain some of the bumbling there. I am not a JFJ fan but when you have three or four guys all trying to gain more power of the Leafs, it can't be a great place to be GM of. The other thing is that while Bowman is a great coach, he was forced out as GM of the Wings and more than anyone, he has to know of the mess that the Leaf front office is in.