It’s the natural life cycle of sports. The foundational pieces age out and they’re really tough to replace without picking high in the draft. Exceptions come with the Detroit Red Wings when you’re able to pull a Datsyuk and Zetterberg out of the late round and actually back fill with foundational pieces.
IMO, Lamoriello had those foundational pieces in Toronto, just needed more time to build around them. Remember, every move has to fit within specific parameters so you may pass on some things or take a different road because something doesn’t make sense at the time.
Lamoriello builds a basic structure. Every player and player type has a place. If he’s able to take this basic structure and add a gamebreaking talent like Barzal at the top, strong blueline and good coach, you get something like the Islanders. They can compete with anyone, but likely bow out to a more talented group.
Take those Islanders and substitute Matthews, Marner and Nylander for Barzal, Eberle and Bailey, and you get a Stanley cup contender.