Does the organization have a problem promoting players? Hard to say. They haven't exactly been bursting at the seams with talent ready to step in so that is the biggest part of the problem.
At times they can seem to block players pathways by making signings like Kevin Rooney, who add next to nothing to the team. On the other hand just look at players like Ruzicka, Dube, Mangiapane, Andersson, Kylington (toss Gaudreau and Tkachuk in there too).
There's at least 7 high impact players that have been "promoted" through the system in fairly recent memory and we still have Wolf, Pelletier and Zary as players that may come through as early as this season as well.
Maybe there's a bit of a trust issue when it comes to getting role players into the trenches, but I see little to no hesitancy to bring in skilled players when they're ready. Phillips may be an outlier, but I think everyone can agree he's more than likely not a top 6 stalwart in the making.
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