This will continue to be the discussion until Lamoriello is gone or the team wins the cup (and then it'd still happen I'm sure).
Vegas is interesting because the bulk of their star talent didn't come via the draft so they demonstrate that you can bring in your top players via trade in order to win. However, Vegas is unlike most franchises because of the way their organization was brought into the NHL and was able to accumulate draft capital land assets to trade, plus I think they had more cap space in their earlier years (I could be mistaken) because they didn't lock anyone up long term on big deals. I'm not quite sure when they hit max cap but I know they reached it before winning the cup.
A team like Florida, though they haven't won, shows a team can be competitive by bringing in castoffs from other teams (Forsling, Verhaeghe, Duclair, Bennet, Reinhart) and I do think they're similar to where the Islanders are. Despite having Barkov, Huberdeau, Ekblad, and Bobrovsky (plus other young goaltenders), they were never really competitive. Huberdeau was over a point per game player during his last four seasons in Florida, so they had all of the makings of a team that should've been challenging for a cup. That didn't happen, they traded for Tkachuk and still weren't that good until they hit the playoffs and they haven't looked back since. How much different does that roster look if they missed the playoffs last year? Had they missed they most likely would've been letting guys walk and shaking up more of that roster. Instead a single point in the standings and a run to the finals has completely changed that organization, now viewed as the best team in the East by many. One last note on Florida, they have a grand total of three players on their roster who were drafted by their organization.
Also worth noting that most of the cup winners in recent memory have abused the f*** out of the LTIR rules. I'm not complaining that those teams cheated, but they were all able to stock up and make trades for players to bolster their lineups because of LTIR and then have a more stacked roster during the playoffs that isn't anywhere near being cap compliant. If your team doesn't get lucky with when a big injury happens then you're not able to do the same thing and that's not the fault of any GM (unless they were presented with the same opportunity and didn't take advantage of it).
I like a lot of what Lamoriello does, from his net out philosophy to having guys play specific roles on the team. I'm not a fan of how much loyalty he shows guys, but I acknowledge there is some value there. It's prevented him from making some tough decisions. I'm encouraged by his decision to not make any moves this deadline because the biggest fear I have is that he'll keep throwing good money after bad chasing a cup before he's finished given his age. I'm not opposed to taking a step back in order to take a step forward for a season but I am opposed to a complete tear town.
We've seen enough talented players get moved around the league and in weird circumstances that I don't see how anyone can say for certain that [x] teams can't improve because of [y]. We've also seen players labeled as "not a winner" who went on to win. For me, the path forward is making tough decisions with some veterans (letting some walk, trading others) and acquiring players who need a change of scenery or a chance to rebound.
Time and time again we've seen teams who were thought to be on the verge of a rebuild (Vancouver, Florida, Los Angeles, Boston) find some way to become relevant again. Whether that's through trading, a new coach, or a GM change. We've also seen those highly touted teams with all the young prospects fizzle out or be unable to reach the next step.
Life isn't linear, enjoy the ride.
