The Edmonton Oilers are in danger of not qualifying for the Stanley Cup Playoffs. Forget about being a legitimate Stanley Cup contender, in year seven of the Connor McDavid era, this team is still struggling to just make it to the postseason
I still think they’ll get in and I’m fairly confident in that. They’ve been a much, much better-looking team under new Head Coach Jay Woodcroft despite the last two losses. They’re going through a tough stretch in their schedule and even if they fall flat this weekend, they’ll have a good chance to get these points back next week when they play three weak opponents. 
Still, the goal for this team at the start of the season was not to simply squeak into the playoffs. They were supposed to be a group that was capable of going on a deep playoff run. After all, their general manager had north of $20 million in cap space at his disposal to give this group what they needed. Last summer was the time when Holland was supposed to put his stamp on this group and give the Oilers two-generational forwards what they needed in terms of a supporting cast.
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To be fair, some of his moves worked. @Zach Hyman has been a near-perfect fit, the contract given the Ryan Nugent-Hopkins was good as well, and @Cody Ceci has been a fairly reliable defenseman given his price point. Holland had a few wins this summer, the issue is that the losses far outweigh those victories.
Tyson Barrie’s contract appears to be borderline unmovable just months after it was signed, the Duncan Keith trade is still puzzling to me, and the goaltending is still a glaring weakness. And glaring weakness is still probably an understatement. 
It’s hard to watch the way the Oilers played in a losing effort on Wednesday in Tampa Bay and not wonder where this group would be with a competent goaltender. The thing that makes this even more frustrating for Oilers fans: they appear to have a competent goaltender sitting in the AHL. 
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@Stuart Skinner has outperformed both @Mike Smith and @Mikko Koskinen and yet, he’s starting games for the Bakersfield Condors. He has the best numbers out of the three goalies and yet he isn’t in the NHL. That makes no sense to me.
Holland made some good moves this summer but his inability to get this team a legitimate starting goaltender is really the only reason why they aren’t firmly in a playoff spot or even competing for the top spot in their division.
I will give him credit for the Evander Kane signing while we’re on the topic. I was one of the many voices that were against bringing him in, but, he’s brought the Oilers a physical, mean element that they really didn’t have in their lineup. He’s scoring as well, which is a big plus.
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The issue I now have is that there are reports that Ken Holland may not be very aggressive at the trade deadline. TSN’s Ryan Rishaug said earlier this week that even though we are one month away from the NHL trade deadline, The Oiler’s main acquisition has already been made. 
If that is the case, it is absolutely unacceptable.
Last season, Ken Holland made the decision to not go all-in at the deadline and I actually defended that choice, saying that you can’t push all your chips into the middle every season and with the amount of cap space the Oilers had coming in the summer, I could see why Holland was taking the patient approach.
Whenever I defended that choice though, I always made sure to add that the 2021 trade deadline was the absolute last time that it would be acceptable for Holland to say that. With the money they had available and the assets at their disposal last summer, there is no reason why we should not be talking about the Oilers making significant additions to this group in order to put them over the edge and make them a Stanley Cup contender.
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The Oiler’s big splash absolutely cannot be the free-agent winger that they signed for just $2 million in cap space especially when they have other glaring holes on the roster. It simply cannot be the only significant move that Holland makes. That’s beyond unacceptable.
Holland has come out and said that he’s more interested in players that are under team control but honestly, considering the lack of cap space they have this summer, I think going after rentals at this year’s deadline is a fine strategy. 
This deadline should have been the time when Holland was putting the finishing touches on a roster ready to win multiple playoff rounds. Instead, he’s still trying to fill holes that have existed since the moment he took over as the GM in 2019.
They still don’t have a goalie, they still need to add a shutdown defenseman, and they’re still strapped with a handful of bad contracts. The only difference now is that Holland can’t say that the bad contracts were inherited. He signed them all, with the exception of Mikko Koskinen, and now it is his responsibility to find a way to improve this team despite those bad contracts.
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It may be easy to say that the Oilers are in a “money in, money out” situation at the deadline but that’s not a good enough excuse anymore. The Oilers are in the cap situation that they’re in because of Holland and now is the time for him to earn his big contract and live up to being one of the highest-paid General Managers in the league.
This trade deadline is not the time for patience. It’s the time for Ken Holland to give Leon Draisaitl and Connor McDavid what they deserve: a supporting cast capable of helping them go on a playoff run.
The coaching change helped. Bringing in Evander Kane helped. Holland should not stop there. He needs to do everything he can to make this year’s team as good as possible. 
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