Poor team building plan and cap management.
Tooooooo much money and cap invested in wingers that is only going to get worse with Kessel's new raise pending.
Something has to give, because other positions of need can't be addressed while ~ 1/3 of your teams salary cap (+$22 mil of 65 cap) is allocated to Kessel, Lupul, Clarkson and JVR, your top 4 wingers.
Yep.
Chicago has been willing to trade away Campbell, Versteeg, Byfgulien, Ladd, etc. And now Bolland. And still won the Cup a second time.
They've identified their core core guys. Not their strong supporting cast members, but their absolute foundational pieces, signed those guys long term, and been willing to get solid value for everyone else via trade.
Our lack of foresight has lead to us having a net negative # of picks compared to what the NHL gives you by default in the draft over the past five years (34 picks in 5 years, 35 is the default), still missing a core piece or two, and not coming out of it with great cap-space going forward either.