It's in the buyout calculation.
They structured the buyouts to stop teams from front loading deals so they could buyout the last few years consequence free. Moulson's contract giving us almost zero savings in buyout is an example of that.
Because of that, the buyout calculation actually favors "backloaded" deals.
Buyout FAQ - CapFriendly - NHL Salary Caps
Right. The idea is that in a frontloaded contract, you're paying more in salary than cap hit in the early years. Essentially, teams get an advantage against the cap for those years. With backloaded deals it's the opposite. There's a larger cap hit in the earlier years for a lower salary. The team is essentially paying "extra" cap space for those years. The buy-out cap hit in both respects partly makes up the difference.
For an illustrative example let's look at three contracts, with the length/AAV, but different salary structures.
Contract A, the frontloaded option: $6M/$6M/$5M/$4M/$4M
Contract B, the flat option: $5M/$5M/$5M/$5M/$5M
Contract C, the backloaded option: $4M/$4M/$5M/$6M/$6M
Let's suppose then that we wish to buy out each of these contracts after year 3. Here's what the buy-outs would look like:
Contract A: $2.33M/$2.33M/$1.33M/$1.33M
Contract B: $1.67M/$1.67M/$1.67M/$1.67M
Contract C: $1M/$1M/$2M/$2M
As you can see the more frontloaded contracts carry greater total cap hits on the buy-out (although the more backloaded ones cost more actual money). The more backloaded carry higher cap hits for the seasons following the end of the original SPC. However, given the tendency of the salary cap to rise, with all other things being equal, it is better to push back the larger cap hits and take the smaller hits earlier.
