The real problem is obvious.... it's management.
If you include this Clarkson idea as well as the compliance buyouts, that is 5 contract buy-outs in roughly 7-8 years.
No other teams have more than two (and most of those were the compliance buy-outs).
Clearly management, whether it be JFJ, Brian Burke, or Dave Nonis. All 3 have crippled the Leafs due to offering "market value" for players that end up not being worth it.
Paying somebody too much is one thing. Giving them a super long term is another, and adding in NTC's/NMC's is an entirely different and idiotic thing.
Most teams use those 3 items to help lessen others. An older player may be offered more money in hopes they are willing to accept shorter term. A player would be given a NTC/NMC in order to lower the salary demands. However, the Maple Leafs offered a 30 yr old physical player a 7-year deal, worth $5.25m per yr, with aNMC and somehow not a single person on staff seemed to stand up and ask if that was a good idea....
Management clearly cannot identify a players value properly. Considering this has happened with 3 different GM's it might be time ti revamp the ENTIRE Pro Scouting/Player Acquisition personnel.