I really hope there's a press conference after the season ends and Malkin announces that they're cleaning house - everyone.
And I think the new GM should look to the past and also modernize the team. I like that certain teams have a character and stick with it. Look at some of the other multi-Cup winning teams. MTL loves skill guys with flair. EDM is similar. BOS has been more of a physical, lunchbucket team, so guys like Chara, Marchand and Bergeron were perfect Bruins to win a Cup. The Isles have a history and character from the dynasty years and should try to adhere to that. A well-coached, defensively responsible, strong up the middle (goal, D and C), big team that has both grit and skill and can play any style. Lou actually did this halfway. But, this team's biggest problem has been the coaching (since Trotz), the lack of high end skill at the top of the lineup, especially finishers, and the lack of PMDs (leaving aside strategic GM moves like excessive loyalty, poor cap management, etc.).
Bring in the right dynamic GM, coach, scouts, etc.. The right coach and system might actually make some of the players that people want to move more acceptable to keep. The D has been running all over the ice under Lambert and Roy, and that's really bad for guys like Pelech, Pulock and Mayfield. And, even in the right system, having Romanov, Pelech, Pulock and Mayfield on defense is having too many guys who don't excel at puck movement. But you can keep at least two of those guys, say Romanov and Pulock. The other four D need to be puck-movers with skill and PP effectiveness. The dynasty Isles, for all the talk of Arbour and his emphasis on D, had more skill guys on D than most other teams at the time: Potvin, Persson, Tomas Jonsson, McEwen.
At forward, again coaching will help make whoever holds over more effective. Like the D, Arbour insisted that his forwards play 2 ways, but he also had Trottier and Bossy at the top of the roster, and then Goring/Brent Sutter as 2Cs for an effective 2nd line. Most of the group was big though, and gritty, and they wore other teams down but also had skill. Even a smaller skill guy like Kallur fit in as an excellent 2-way player and PKer. This won't be an easy fix, but if a new GM can figure a way to get a player or two at the top of the F group to push everyone else back a slot or two, that would be huge.
The league tends to go in cycles. Lately things have tilted towards skill and speed. That's not all going to go away, however defense still matters and it still wins, but it needs high end skill mixed in. And size matters too - all thing being equal, a big, fast, skilled guy will beat a small, fast, skilled guy in a contact sport, especially one with 4 playoff rounds.
Finally, never go into a draft without a 1st round pick - really have at least one in every round. Constantly keep the pipeline full of replacements. Sign a couple of UFAs to 1 year deals each summer for depth that allows you to keep youth in the AHL to start the year. With a good scouting staff and development you'll have more hits on picks and therefore more skill and more depth. The depth allows you to trade a couple of vets (maybe the same guys you signed as UFAs in the summer because they were replaced by mid-season callups) at the TDL and get more picks. Rinse, repeat.