I think for his entire career Lou should definitely be up there
many people hate on him for some of the moves he made (and I can't fault them) but he is overall pretty good. the one thing I hate is that he doesn't negotiate with players during the season. but, Parise wanted to play with his boyfriend, Niedermayer back in the day wanted to play with his brother, Gomez chased the money, etc. those are things that is really out of his control.
but he had a great year last season IMO with all the reclamation signings, hiring Deboer, etc.