Leafs would prob have had the next dynasty if their top 3 players didnt demand such high contracts so quick. If they would have just waited it out...like the Pens and Hawks players did, they might have won a few cups by now.
Would have had the money to add a dman like Pietrangelo those years as well. Maybe a Krug and Pietrangelo at the same time if they chose to go that route instead of filling out their bottom 6 with more depth.
Horrible luck for the Leafs since at the time everyone was signing big deals(after McDavid did)...imagine if it was a few years later. Like now for example. Probably have Matthews at 8 , Marner at 7, Nylander at 5. Tavares at 7 or 8. Saves what...12-13mil? Even 8-10 mil would have made a huge difference allowing them to build a cup winning team.
The Pens and Hawks are both bad examples. They both won their first cups when at least some of their superstars were still on ELC deals. For the Hawks both Toews and Kane were on the final year of their ELC. For the Pens Malkin was still on his.
And the Pens superstars didn't wait for big contracts. At the time of their signings coming out of ELC both Malkin and Crosby signed for a higher % of the cap than any of Matthews, Tavares or Marner.