Teams that challenge consistently for the Stanley Cup have established a culture where players take less on their contract than they could get elsewhere in order to leave cap space for other good players. The best example is Detroit, although New Jersey (prior to Kovalchuk) is another.
Teams that are consistently at the bottom of the league, or in less attractive locations, have to overpay to get players. (See Edmonton, Columbus.)
Toronto has a history of overpaying. Part of this is because they can afford to. Another reason is the fans and media having a hissy fit if a fan favourite is not signed. (See Luke Schenn, circa fall of 2011.)
Schenn and his agent played hardball last summer and ended up with a contract that I believed was at the very top end of the range based on his play last season. Based on his play this season, he is significantly overpaid.
Burke and company have a dilemma. The team is not good enough yet to attract elite free agents who want to play for a Stanley Cup contender. If they continue to overpay for players that are less than elite, they will never have the cap space to develop a Stanley Cup contender.
I thought that the Liles contract was interesting. I am convinced that he could have gotten significantly more on the open market this summer. Has there been another time in recent memory when a Leaf player gave a home town discount? It will be interesting if Grabovski does as well.
The Leafs have to stop overpaying for free agents. But they also have to start looking at trading players, like Schenn, when their contract demands are more than what they are worth.