How Do the Maple Leafs, Islanders & Lightning Fix Roster Problems?

The first round provided plenty of takeaways for fans and experts alike but for a few teams, there was one big theme that stood out. The New York Islanders, Tampa Bay Lightning, and Toronto Maple Leafs won't win a Stanley Cup title with the core they have right now. There's a common question in the NHL when it comes to team building. Can a team win when a significant amount of the salary cap is taken up by four players?