It was a typical Leaf tradeline move, trade a 1st for a good player who's past their prime. Prime isn't always about ability, its includes durability too and gritty, power forward types age in dog years. Theres no doubt if healthy he gave this team what we need though.
How many bottom 1st round picks are in the NHL let alone on the Leafs?
However many you find, there will be even fewer plucked out this year.
You can't worry about 4-5 years down the road if you decide you have a strong team today. Leafs had no Cap space and finished first in their division. You go for it or you wonder "what could have been".
Some teams are a merry-go-round of 1st round picks who never make the big splash. I think of the Oilers a few years ago when Taylor Hall was there. They had year after year of top picks, nothing to show for it.
Who wants that?
I have no problem with the trade. Leafs were always going to pay a premium, and usually do because of the pressure. It's one reason why I say just
get rid of the hard tax and make it a luxury tax, that way Leafs can have many more options they will simply pay with cash rather than draft picks and won't be resigned to a smaller number of players at the deadline.