Quoting: MitchMarnerElite
Again with the mention :P haha! So issues with both deals. In my books, a young top-6 winger that's scored 20 goals in his first full NHL season (last year) is worth at least a 2nd round draft pick and a pretty good prospect, at minimum. Just because the Leafs are cap-strapped, like many others are, or will be soon, it doesn't mean the Leafs should, or would sell low on such a player, any player for that matter, but especially when you are looking at more of a cap-efficient futures package in return. Second, my issue with Matt Roy. It's not so much an issue, as a risk. He's a good young defender, no doubt, he plays the right side and comes with a super cheap 1-year left on his ELC deal. He also has good hit and shot block numbers, which equates, for a lot of Leafs fans as, young, controllable, tough, plays right side, check-check-check, which equals an automatic good fit. Now, I am not saying he's not a good fit. Ideally, the Leafs would pair him with Sandin and let them develop together against oppositions less elite players, but the cost you have woah, that's my issue. To me, a 1st would be out of the question, which might mean the deal needs to be bigger. For the right price, I would definitely take a swing at Matt Roy, but I am not sure I see a scenario where the Leafs wouldn't have to overpay. LA is rebuilding, so why in the world would they want to part with a good, young and controllable piece? If LA was prepared to do a hockey swap like Dermott for Roy, I think the Leafs would strongly consider, especially because Dermott is occupying Sandin's lineup spot.
Overall, I think more drastic lineup changes will be needed, both in terms of where there cap situation stands and in terms of how well (or lack their of) they do these playoffs. I would add that when you are trying to make these deals and setup a roster that hopefully takes things to a new level, you look to other teams that are not rebuilding, because I think non-rebuilding/retool clubs would be more likely and willing to make hockey deals.