Recently heard a podcast about the Moneyball Oakland A's and how being in a small market they were sheltered from the criticisms of Media and a rabid large fanbase. Sheltered enough they could get away with fielding that Moneyball team in the first place and able to experiment. I think the Media attention Canadian teams get and the need from the fanbase to always compete has a negative effect, pushes management to doing Win Now moves that may not be optimal from a long view stand point, a long view standpoint Canadian fanbases don't have the patience for. I think in the case of the Leafs their own hype and expectations lead to a sub-optimal team build and overpaid contracts. Montreal's last gasp for a Cup no one in the market at the time would probably have wanted anything else. But that's my viewpoint from afar, I won't speak for these markets as they are outside my focus.
I can speak for my Oilers though and there's no doubt Chiarelli was a joke of a manager. After his tenure it was reported that he pretty much did his own thing without input from those around him. Acting like a cowboy and using the Oilers organization as his own personal ego trip and fantasy team build. Eberle->Strome->Spooner was trash, although the original Eberle to Strome trade made sense from a needs aspect, who knew Strome would go goal-less for an entire season (an outlier in his career) to reduce his value to that of a cap dump. Lucic was no protection at all, the issue with Lucic is signing him in the first place under an outdated and misguided notion on the role of the enforcer. We wanted the new Semenko for McDavid. An enforcer role we could and did fill for much less dollars with the cheap pick ups of Kassian and Maroon. Lucic to Neal was a Holland move that I agree with though, Lucic was done and bringing a failure/mopey attitude to the Oilers and short term cap relief was needed for that season to get the Oilers back on track. Reinhart another trash Chiarelli move. Puljujaarvi another trash Chiarelli pick, after he was already busting and his agent started meddling, the writing was on the wall, even when he first asked out there was no interest and no value there, Holland did try to move him and it made sense to just see if he could develop. Koskinen another bad Chiarelli move. Smith, not so much, for 2.3M he provided above average Starter level performance, best value contract for a Starter at the time. Another trash move by Chiarelli with an okay move by Holland. Campbell is squarely on Holland's shoulders though, I never wanted to sign him in the first place, it was apparent that was a bad bet from the onset.
Your assessment pretty much breaks down to Chiarelli being a shit-tier manager which no one will disagree with. But then Holland doing an pretty good job to finally create a contender. The Hyman signing. The Ekholm trade. The Kulak trade. Kane signing. Perry signing.
Moving forward I don't think any GM avoids the Offer Sheet situation that was already in place before Bowman took over. But last I checked the loss of Holloway and Broberg, and replacing them with Podkolzin and Emberson hasn't changed our chances. And 2 of 3 of the Free agency signings are looking like good bets. I think it's too early to say the new management group is bad.
