One thing we forget in 2008 is just how badly the team was managed under John Ferguson Jr. My nostrils still flare up when his name is brought up because he inherited a team in 2003 that was a Cup contender and then ran them to the ground. There were 5 players on the Leafs with a no-trade clause. Sundin, Tucker, McCabe, Kubina and Kaberle. Outside of Sundin, no one deserved a no-trade clause. This is like Marner having a no-trade clause - which he does - but giving one to a 3rd liner for the heck of it. It made no sense. And why Sundin got all of that flack is beyond me. He didn't deserve to be forced out of town like that, or guilted into doing it. How about the other 4 guys who didn't deserve the no-trade? Go after them, not Sundin.
I do remember the situation they were in back in 2008 and they went on a bit of a tear late in the season when the games didn't matter anymore and they were out of a playoff spot. It was really annoying, because all it did was push us further and further down from a high draft spot. We ended up choosing 5th, and it was Luke Schenn. He's fine and all, but ahead him was Stamkos, Doughty, and then Pietrangelo 4th. All won the Cup at least once, two were captains (Doughty may as well have been) and probably all three end up in the HHOF although Pietrangelo will be the "maybe" one I guess. With a trade or two maybe we move up higher, maybe we pick one of the other guys and they lead the Leafs to the Cup. None of this is Sundin's fault of course, but with that tear they went on at the end of the year I can remember hating every time he or any of the Leafs scored big game winners.
That being said, it was a rare time the fanbase didn't like Sundin. There was always the whole "We'll never win with him as captain" talk. But even those guys still knew Sundin was good and his supporting cast was traditionally bad. I don't blame him for staying where he was comfortable, however, he'd have a Cup if he was in Detroit. And since Ray Bourque is still loved in Boston despite winning a Cup in Colorado I think Sundin would still be a Leaf even with a Wings Cup. I'd have been happy for him to be honest.