He overpaid and he knows it. The problem for him was that he felt compelled because EVERYONE overpaid (except Florida on Marchand), especially those in our division and he had to decide "do I make the executive decision to overpay and improve the team at a great expense of currency (1st Round Picks, something they have continually done for this failed core), or, do I sit back and pick off some cheaper options but not move the needle much, saving my capital for next year"?
Watching this team as I have for these years, it is clear to me that the latter option was better, wait until the cap goes up and use your capital on the right kind of team he might have NEXT year. For him in his position of employment, appeasing his team and boss, that luxury may not be so easy to embrace. It puts him in a difficult place to decide to NOT go for it. That said, he did get some term and good salaries, but he paid a bounty for these two because 1st Round Picks are gold in trade (most years).
Now, there are valid arguments to be made that maybe he didn't overpay since these are needs the Leafs had. Objectively, I'd have to disagree. This year was particularly bad for excessive overpayments in the league, but at least he did well to have these players with 1.5 and 2.5 years of contract remaining, AND, he coordinated to have some of the salary eaten. That could be important going forward. I still would have tried to hold the line but I guess the team will approve and they are on very good contracts.
Here is the true barometer of whether these were great pickups: how do they do this playoff? After this many years of being fooled, this is the only metric that is relevant.
Not one Cup winner should ever worry about the price they paid in the future as long as they win. Think of the Raptors and their courageous pick up of Leonard, which turned out to be an expensive rental. No one cares, just win.
The problem is this has been tried again and again with this core bunch and it has never succeeded. Years of 1st Round picks traded with no reward.
I just want them to stick to their guns IF the Leafs falter again and walk away from JT and Marner. I said if they make it to the Finals, pay them their money. If not, accept that it's time to finally, mercilessly, move on. You can then fit the right type of pieces consistent with these guys. Hard nosed, tougher to play against while Knies and McMann develop for another year.
I don't care for 100 point seasons, win when it matters.