Its the GM of the year award. Not the GM that won the Cup award.
I mean winning the Cup is the goal, but he's had how many cracks at it. While Drury stepped in and all the moves he made got a non playoff team the last 5 years to the ECF his first season. All the additions sans Blais made major contributions.
What's the point of the award then? It's the same thing as the Hart. Why is it always the highest scorer. There's already an award for that. McDavid isn't the most valuable to his team. Draisaitl has something to say about that. Shesterkin was BY FAR the most valuable to his team.