Not so sure the Iginla trade was that dumb (if that is what you're referring too). Iginla is pretty much a loan player. Once the season is up if they don't win the cup he will likely resign back with Calgary for next year as a UFA for more money.
Keep in mind he is still younger than some of the other players up there, he probably has 3-5 more years left before retirement.
While the trade looks really dumb Calgary pretty much got picks and their Captain back to effectively "rent" him. Granted Iginla could say 'screw it' and sign with Pittsburgh again next season as well.
I'm mostly talking about the last 6 seasons of pretending they just needed a couple pieces to go on another cup run. If Iginla signs back in Calgary then the trade is a good deal for them. I'm not so sure he will though.