If you want to win the SC and have a 3-4 year window to do so, you'll need to sign some 8-year contracts that will sting at the end of your window,
The alternative is to trade those guys and try to remain in contention for a longer period. But you'll have weakened your team during your prime years.
GM's need to understand (and most do) that a team cannot be in contention forever in a cap world. So, you maximize your roster while you can and make deals that will look bad in the 2nd half. Everyone knows that signing Ryan for 4 years would have been better for Nashville. But that choice wasn't here. So, they sign him for 8 years and get ready to eventually plug their noses.
If Calgary is still contending when Johnny's and Monny's contracts are up, they will also likely get 8 year's nose plugging contracts as well.
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