One thing that always bothered me about the punishment was that we only ever got information that Dorion acted alone. It's a hefty fine due the actions of 1 person. Would have made more sense to fine/punish Dorion directly as it holds him solely responsible.
Now, if there's some information in the report that multiple people knew about the mistake and didn't act to resolve it, I can understand the punishment being that substantial because it indicates a level of carelessness that's pervasive throughout the organization. However, there have been no rumours or any additional fallout that points in that direction so the penalty seems extremely excessive.
It's like if a player punched out a referee and the NHL fined the organization in addition to suspending the player. Why does the organization bear responsibility for the actions of 1 person?
I can see the logic with punishing both the club and the executive.
If a GM were on their way out, the owner or top manager could ask them to lie on a trade call and provide them with some sort of exit bonus, or provide them with some sort of additional incentive down the road that cannot be tied back to the situation. They are going to be fired anyways, and the consequence of being caught is being fired. If there is another Pierre Dorion, they might look at it like they have one foot out of the league anyways and aren't guaranteed another GM or AGM job, so they better play ball with the one connection they have and hope they don't get caught. If the team doesn't get punished, it can create those kind of incentives.
It's similar to Arizona breaking the rules in regards to fairness with the draft and testing prospects. The league wants to ensure that organizations as a whole have incentive to follow the rules.
The primary criticism of the draft pick is that if you go by what Andlauer claims, it wasn't communicated to him properly during the sale process, because that may have reflected negatively on the value of the team. I would have to go back and check to see if he straight up said that the opposite was communicated to him (it was resolved and over with). The criticism is not that the NHL should not on paper punished an organization.
Ironically, a more appropriate punishment would have been fining Melnyk while he was still alive. Because the entire purpose of the trade was to clear cash. If you want to really break it down, giving up a 1st multiple years in the future to get back a 3rd and dump 10 million dollars of cap isn't bad value. So even from a punishment perspective, it was pretty light. Had the Senators given up the 7th overall this year, that might have been different.