The issue was - Georges is/was a terrible hockey player and Bolland wasn't going to be worth anywhere close to his contract demands. Those were two clear mistakes fortunately Shanahan got bailed out by luck.
The thing though what makes shanahan a good hockey manager is that he clearly learns very quickly from his mistakes (for the most part).
Folks shouldn't be afraid to be critical of even small mistakes because eventually multiple small mistakes can lead to a rather nasty one.
I haven't watched a lot of hockey this year because of my crazy work schedule. But, I maintain that out of all the issues that Buffalo has - I don't think Josh Gorges is anywhere near the top of the list. Please note, I'm not saying that I would have liked that deal or anything like that, just that if it (or they) why, specifically would that have sucked? is Gorges being torched for goals? He is completely brutal defensively? And if he was here and being deployed by Babcock is he as "terrible" as you think he'd be? (I mean people have been harping on Polak/Hunwick for ages, and how bad they were - until they weren't).
If he is - i'll totally take it back, and say yah, phew, the Leafs got away with them. That's all i'm saying.
So the fact Dave Bolland sustained a career-ending injury means the move would've been okay? Just because you're "saved" from a bad contract doesn't make it okay. In addition, LTIR isn't free cap space. Thats why Florida had to package a high 1st to get another team to take him. LTIR is part of the reason why the Leafs will have close to 5 million in overage penalties for next year. No matter how you slice it, that Bolland contract is a nightmare and the Leafs dodged a huge bullet (thanks Florida).
To your second point, Gorges is not the problem.... How isn't he? He's way past his prime and is a terrible defenceman. If Buffalo didn't have so many terrible defencemen like Gorges they would've have a dramatically different season. On top of that, the deal on the table was Gorges for Franson. That means we wouldn't have gotten Dermott, Bracco, Dzierkals, Leipsic, and Mattinen.
I understand supporting the management. Overall they've done a phenomenal job. But call a spade a spade. That offseason was so close to becoming a disaster.
and if they did sign them, I would have felt that they would have worked a way to eliminate the problem. They've been doing that since the word jump. I have never said the management was perfect and hadn't (or will not) make mistakes. the actual key point i have always made is how they get rid of them and how much will the blow back hurt the Leafs.
I'll be dead honest I don't know what overages means or is or whatever. So okay point to you. However. at the time when everyone was healthy and whole, I could understand why Shanahan would want to have a Bolland (or a Gorges around). I'm not even going to play the "He was listening to Nonis and Nonis was trying to save his job." angle. Let's say these were types of players that he wanted because he knew he was going to strip the team anyway. Maybe he identified that even with their flaws, these were traits he'd want to have in the room with younger people.
Maybe he identified that he was going to be stripping the team and he wanted to have some players he liked/trusted around. I don't know.
(I think part of this "issue" is - no one expected the Leafs to get Marner (and have him be impactful so early), the Leafs winning the lottery (because if we had Pulju or Joleivi or even Tchachuk, all of them are back in the minors or in the A). or being this good). so then you can cycle back and go - yah THOSE WOULD HAVE SUCKED. well yah. because we're actually this good and we can make awesome moves with a lot less cap space. but if those things didn't happen then you have some sort of support around a team that's stripping talent and trying to build from the ground up).
maybe it would have been a disaster. but maybe Bolland doesn't get injured and he (doesn't live up to that contract), performs decent enough. Maybe under Babcock, Gorges isn't horrible/terrible. So maybe the off-season isn't a disaster. (i mean maybe it is, and you're right but we'll never know. thankfully).
and to tie it all up here - that still doesn't mean this contract is bad. i personally don't think so - and if it shows that it is I think the Leafs know how to get rid of it relatively quickly.