Quoting: OldNYIfan
I've always felt that Dean Lombardi made three great decisions: acquiring Marian Gaborik, acquiring Jeff Carter, and acquiring Mike Richards. And I've always felt that he made three (predictably) horrible decisions: acquiring rental Anton Sekera, acquiring rental Milan Lucic, and not using the compliance buy-out opportunity to get rid of Mike Richards.
Ehh, I think he also paid people for past accomplishments instead of likely future accomplishments. Specifically Brown. Brown was underpaid in his prime, then paid what he should have made in his prime, for a long term deal after his prime. He declined pretty quickly, but fortunately for them he than plateaued and stayed the same.
Doughty, I kind of see how they were forced on this one but similar.
Quick was a smart cap abusing deal, but he aged about 3-4 years ago and that really hurt them
They then failed to build the next generation of the team, and essentially have only about 4 guys entering their prime now, a couple are solid but none game breaking in Kempe, Iaffallo, Roy and Walker. Fortunately the next generation after that is looking good