Every team has some bad signings -- but Carter and Brown is hard to knock-- Brown was key contributor to the first Cup win, led the team in scoring, and Carter the second, also among team leaders; and Carter has scored 25+ goals for them in three straight seasons, including the strike season. Sharp, Bickell and maybe even Crawford for Chicago but they also moved plenty of good goales and nickle and dimed Crawford, before finally settling on Crawford long term. But Crawford has won them Cups. So, there's that.
LA also made moves between their first and second Cups, moving a bunch of non-core players. They moved Dustin Penner, Rob Scuderi, Colin Fraser, Andrei Loktionov, Simon Gagne, not terrible players, but not core. They then had the cap flexibility to bring in Gaborik who played a key role in the 2013/14 Cup win.
By comparison, they move Penner, we lock in Chris Kelly to an overpaid contract. Oh, and we sign Simon Gagne last year, years after LA traded him.
I'm not sure if you're referring to me, but my big critique of the Boychuk trade is not necessarily that he was moved (though in hindsight, that was a bad decision with Seids' regression), but the fact that Chiarelli made zero moves over the entire summer to free up cap space, so we'd have the flexibility to retain Boychuk and start the season cap compliant, if the offers out there were not good, and instead move him at the deadline. Boychuk should have fetched a much, much, better return. Or, in the alternative, do not re-sign Seids and instead commit to long term to Boychuk before his trade became inevitable.