Fans and media all have players that they simply like more than others. That’s a fact. Certain players get a little bit more leeway depending on how you personally feel about them. You tend to forgive the mistakes of players you like a little bit easier.
Look at how fans react to Kris Russell. Some will say that he’s one of the Oilers best defensemen because of his compete-level and willingness to block shots while others look at his numbers and puck-moving ability and think the Oilers would be a better team without his $4 million cap hit.
Just like how fans have certain bias’ and opinions, so do coaches and General Managers. I remember points last season when fans were irate with Todd McLellan’s love for Drake Caggiula while he seemingly never wanted to give Jesse Puljujarvi the same opportunities, despite the General Manager clearly wanting Puljujarvi to get more ice time.
Maybe that loyalty isn’t so much built from the player personally, but it’s a result of a General Manager wanting to be right. Peter Chiarelli likely would have never dealt Adam Larsson because it would mean that he’s accepting that he lost the Taylor Hall trade. Chiarelli forced Puljujarvi into the NHL so that his draft pick would make him look good. Maybe it’s even a little bit of an ego thing.
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The best managers and executives learn how to accept when they’re wrong and they know when to put personal feelings aside. Look at Bill Belichick in New England. The cliche around him is that he will cut Tom Brady the second that they have a better quarterback. That’s the way championship organizations operate. Loyalty can sink organizations to some extent and when the Oilers name a new GM, I expect that person will come in and feel no loyalty to anyone on the roster outside of Connor McDavid.
That’s why the upcoming offseason for the Edmonton Oilers seems so unpredictable. The man who brought in a lot of the Oilers current depth players is no longer here and when the new GM will likely have no problem moving out anyone on the roster, regardless of how they got here.
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That applies to a lot of players including the aforementioned Russell, who is a prime “cap-dump” candidate. The previous regime clearly thought very highly of the rugged defenseman, it’s tough to tell if the next group will feel the same way.
Same goes for Zack Kassian. The last group of management saw what he did for them in the 2016-17 playoff run. He’s proven that he’s capable of sliding into the top six for stretches, and he finished this past season on a ridiculous hot streak on Connor McDavid’s wing, but for most of his time with the Oilers, he’s been a fourth line winger. The next GM might look at his $1.9 million cap-hit and feel like the Oilers could replace his contributions with a cheaper player. He might also see Kassian as a realistic top-six option. It’s hard to tell.
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The list goes on and on. How will the new GM feel about Matt Benning? He’s 24-years-old and has played in 200 NHL games. With right-shot defensemen like Ethan Bear, Evan Bouchard, and even Joel Persson in the system, I wonder Benning could be dealt for a young forward. The blue line is an area of organizational depth for the Oilers. 
On a deeper level, there are many who think that the Oilers need a massive shakeup this summer. A lot of people will point to the big trade that Calgary and Carolina made last summer as a prime example of what the Oilers should do. The Flames sent Dougie Hamilton, Michael Ferland and the rights to Adam Fox to the Hurricanes in exchange for Elias Lindholm and Noah Hanifin. The deal worked wonderfully for both teams as they each returned to the postseason.
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On one hand, I think we could definitely see that kind of trade and it might involve names like Darnell Nurse, Adam Larsson, Jesse Puljujarvi, or even Ryan Nugent-Hopkins. I don’t think it would be a good idea to trade someone like Nugent-Hopkins, but the incoming GM might want to make a big swing and put his stamp on the team early in his tenure. The other side of that coin is that the Oilers could also choose a more cautious GM who may want to watch this team with his own eyes for a season before dealing off a core player.
Three of the top candidates for the GM job (Burke, McCrimmon, and Hunter) have never been NHL GMs before so once the Oilers make their hire, we won’t have an NHL track record to reference. We know McCrimmon has been solid in the pro-scouting department with Vegas, Hunter has a reputation of being someone who is big on drafting and developing, and Burke is maybe a little bit of a wild card. Whereas if they were to hire someone like Ron Hextall, Mike Gillis, Ken Holland, or Dean Lombardi we would be able to look at some of their past moves and maybe project what kind of team they would like to build. That’s not really the case with a first time GM.
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Whoever the Oilers hire could come in and feel no loyalty to the current roster which could lead to some fringe fan favourites being moved out of town or possibly some massive changes to the core. At the same time, the new GM might be handcuffed by the salary cap and that could lead to the 2019-20 Oilers looking very similar to the team that missed the playoffs this past season. In short, this summer is going to be a very unpredictable one around Edmonton.