Nothing kills and NHL team faster than having bad-money deals. The Toronto Maple Leafs have had quite a few of those over the past few years. Darcy Tucker. Jason Blake. Jeff Finger. Mike Komisarek. Colton Orr. Luke Schenn. Mikhail Grabovski. John-Michael Liles. Joffrey Lupul. David Clarkson. Phil Kessel (the second time). Dion Phaneuf. Those are a list of players that were signed to 4 or more year deals, with a pretty high dollar value over the past 8 seasons. Almost all ended poorly, through buyouts, demotions, and salary-dumping trades.
The problem with the players listed above, is that when the Leafs signed them, their average age was 29.