from Ken Campbell of the Hockey News,
So what does Holland do now? Well, the next calendar year will almost certainly tell the tale. If he is still the Red Wings’ senior vice-president after the summer of 2020, you can probably count on him being a Red Wing for life. He’ll be close to 65 years old, he’ll have been out of the game for a year, the Seattle expansion team will have chosen its GM and the ship out of Detroit will have sailed.
Another thing that will almost certainly dictate whether Holland stays in Detroit or goes somewhere else is how much Yzerman leans on Holland, how much he makes Holland part of the decision-making process and how engaged and invested Holland feels in the future of the Red Wings.