Find a team that won a cup without depth.
I also think depth is critical for a team coming out of a rebuild. I think this is a factor as to why teams like Buffalo (and Edmonton prior to McDavid), never see to get off the ground. It is not the only reason (overall management, poor coaching, and culture are huge factors involved here), but a lack of depth certainly is critical.
Think of how deep Chicago was organizationally when guys like Toews and Kane were added. Their depth got squeezed out, and that was the end of Chicago being able to win. It wasn't just about winning a cup, it was the ability to put those superstars in a position to succeed.
This is how I look at San Jose and feel that they are probably a team that will succeed, versus Chicago that I am a little more iffy on.
I like the fact that Calgary's system is deep. I like having Zary and Pospisil on this team, as they help lead by example, can bridge the gap between vets and young players, and help set the culture. As more young kids pop organizationally over the next few years, the more likely the top superstars that the Flames will (hopefully!) draft will have an easier time breaking into the NHL and turning it around.
This depth provides a good environment for these kids to develop properly in the NHL. You also need a coach and the buy-in from management to follow-through with development. This is an area I think Calgary screwed up with Bennett, for instance. Some kids need longer runways, and if you are investing a high pick, then sorry, it isn't always about 'never given, always earned'. You put prospects in the best position for them to exceed. Not over-expose them when they are not ready, and not bury them when they need more patience. It is a fine line.
I really like this build so far. it is early, but things are looking like Calgary will be adding a top pick this year - plus they have Vegas' first round pick too on top of this. Plus they will be adding more picks. This is a very good build so far.
The only issue I have is that perhaps the Flames should find a way to open up a couple of spots to keep Gridin, and perhaps another spot for a revolving door of Suniev, Stromgren, Morton and Kerins to all get reps in throughout the season. Ditto on defence - Kuznetsov, Poirier, Brzuestewicz as well as Cicek (older) looking like they should be getting reps in. Juggling waivers is an issue of course, so they will need to properly manage that, but the waiver eligible guys should be getting more looks as part of their development.
Gridin sat out last night, even though there are two regulars out of the lineup. That's not a lot of room for young guys to get reps in, especially ones that just need a bit more runway at the NHL level to push through. I get it, it is early in the season and you don't want to 'throw in the towel', but at some point this season, the Flames need to really flip that switch and prioritize development like they did in 2013-2015.
At any rate, I am really positive on the direction of this team, even though I am not happy with the outcome of games at the moment.
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