Let's face it, the Leafs are overpaying, period. That is a relative term as these players make them a great deal of money, though even 10 pylons would since corporations overpay for tickets.
From a fans standpoint, I don't care if you give some kid $9M or $25M a year if you are making profits. Unfortunately there is a cap to contend with, and a weaker team isn't as appealing to watch.
If a management isn't calculating all of these considerations before hand, they have no business being in management. The Marleau contract aside (that's on Crusty Lou), I hope this group knows what they are doing. Dubas and his team have to take a step back before any key negotiation. No one player ensures a lengthy NHL playoff run. Ever (though a Lights Out goalie comes close).