I mean, you pay your scouts for a reason. If the entire Leafs brass thinks, for example, Jake Sanderson or Jamie Drysdale, is going to be a top-pair, #1 type guy (which I am not saying because I am not a scout), and you can turn three years of Rielly (who realistically we are in tough to keep) into this plus capspace (which in itself has value), thats why they get paid and we get trophies for liking 50 posts or whatever on HFBoards. In fact, Kyle Dubas routinely cites the book "The Score Takes Care Of Itself" which is a book about Bill Walsh and the 49ers and they talk about being realists and recycling players at peak value they know they cannot (or should not) keep for long term assets with an eye towards longterm contention (something Shanahan and Dubas frequently talk about). Winning a trade is seldom about just receiving a thing that you think is equal or better in return (aka winning a "bad" trade which happens but, let's say, shouldn't). It is about getting surplus value another team doesn't know they are giving up (a team thinking they are trading a mYsTeRy BoX but actually trading a top pair/#1 defencemen).