General Managers need to roll the dice more often than they actually do. In Cliffs case, he probably did so more than he needed, but, at the very least, he was constantly trying to find the right combination to win.
The more darts you throw the more you are going to get burned (and also succeed from time to time).
For me, it wasn't a trade of Cliff that soured me, but rather the non-trade of Sundin when Cliff was hired to run clean-up duty after JFJ was sacked. Sometimes, a franchise has to put it's character and reputation above immediate gain, something the Leafs hadn't done in years past (they are far better now).
The Leafs should have asked Sundin a couple of times gently and honestly to waive and accept a trade, explaining in detail why he is being asked ("it's not you Mats, it's me"), and then quietly and respectively accept his word if refused. Sundin was not just the leader of the Leafs and it's only star for so long, he was the rock who always carried himself well in public.
I recall Sundin getting called out by media for being "selfish" for not waiving and thus "hurting the Leafs". He shouldn't have been treated that way. I wanted to see him traded for assets too, simply because of where they were, it was strictly business.
However, as a man, I respected Sundins desire to stand his ground and see it through, whatever his reasons. He earned the full NTC and delivered for years, whatever he chose, it was his right. Take a man at his word and show some respect for what he accomplished. Often single-handedly on some of those weak teams.