Over how many different eras of management? The only thing that really makes sense to figure out now, is what Holland did or didn’t do, and Bowman. You can keep going back for the gripe factor, but I don’t see the sense in it. We all know we sucked during the DOD and blah blah blah.
I think Holland was a mixed bag, but I can’t argue with the results, it got us to a game 7 cup finals. From there, let’s look at what Bowman’s doing.
There's been an ongoing theme with the Oilers hiring GMs that left their previous teams in disarray. While the Bruins have remained a respectable team after Chiarelli's departure they still haven't reached the summit despite coming oh so close. And they did have to shed a few players due to his mismanagement. The Bruins have kind of an OBC of their own but obviously Chiarelli's tenure was basically a disaster here.
In comes Ken Holland, who left Detroit completely barren of prospects due to a combination of selling off everything to keep the wagon going and just piss poor drafting when the team couldn't make the playoffs anymore. Seriously, go look at their picks during the 2010s. Oh and they also had a few really bad contracts that Holland signed. Obviously every GM has those especially those desperate to keep a playoff window open but regardless... I will certainly give him credit for a few things. Hyman (prior to this year) has been excellent and Mattias Ekholm is probably the best trade the team has done in a generation. Kane was a solid pickup (even if I'm not in love with his extension). But then come the blunders. The big ones are the Campbell and Nurse contracts which have hamstrung the Oilers not only due to the cap hits but forcing Skinner to take the starting goalie role before he was supposed to. But there were also smaller yet still impactful ones. The Lucic/Neal on the day it was announced was a win for the team but in the end it's at best a wash if not a loss because we're still paying for Neal's buyout this year while the Flames aren't paying Lucic anymore. Campbells and Neal's buyouts take up just over 3m in cap space that we certainly could've used during this offseason. Zack Kassian was a good story while he was here and I didn't mind keeping him around as he seemed to be a decent fit with McDavid. The problem was that Kassian would disappear for long stretches of time and when his extension was signed (Jan 29, 2020) he was in the middle of a scoring drought (I'm pretty sure he was moved off McDavid's line around this time) that he would never truly recover from. Whether it was off ice issues or what have you... It was a mistake to sign what was essentially a depth player to a lengthy deal and the rest is history. Trading Kesselring to Arizona for Bjugstad is definitely biting us in the butt. Sending a couple of seconds to Detroit for AA was also stupid.
But Holland's biggest failings come at the draft table. He deserves credit for turning Reid Schafer into Mattias Ekholm, especially since Schafer's numbers aren't exactly sparkling. Time will tell how much Broberg and Holloway blossom, but obviously they aren't doing it here because of mismanagement from both Holland and Bowman. Apart from those two players though.... Nothing. Bourgault was traded for.. well, not much. Lavoie was lost to waivers. Akey might prove to be something but not anytime soon. And the rest are just the usual crop of Oiler picks that will never amount to anything. 4 years and not a single pick playing for the team, and only 2 that are actual NHL regulars. Oilers drafting has been really bad for a long time and it might have actually gotten worse under Holland.
Finally, in comes Bowman. He did win Cups with the Hawks but was also forced to continually sell off pieces due to cap mismanagement. They fell off a cliff after 2017 save for one series that I won't get into, and have been basically a bottom feeder ever since. This is again due to asset mismanagement and poor drafting, although at least his track record there is better than Ken Holland's. But prime examples include the infamous Seth Jones trade and signing (and Holland helped it happen), the Saad trade, and the Panarin trade. Obviously it's too early to judge his tenure here but his track record isn't exactly the greatest, especially since he's been out of the game for a few years.
While this is just speculation on my part, there does seem to be a pattern of hiring Hockey Canada buddies. Nepotism is nothing new to the Oilers organization, of course. We all know about the OBC days, but I feel like we've swapped one OBC for another. I'm pretty sure that bastard Bob Nicholson is still with the Oilers somewhere.
Oh, and one thing about the Ken Holland hiring that should really irritate Oiler fans is that they were actually looking at Bill Zito (he of the team that just beat the Oilers in the Finals) before pivoting to Ken Holland. Just maddening stuff. I truly hope that Bowman is something special even putting certain things aside, but the early returns haven't really inspired much.
