I think we can only judge by hindsight.
Sofar, Dubas is doing more good than bad.
His drafts strategy of trading down a few spots for more picks will work out more often than not over the long run. He might have missed on Aho but did hit on Sandin and Robertson.
His development program is very good, not just making sure guys drafted in the top are developed properly but also guys like Moore, Holl, Marchment along with AJ and Engvall-really late round picks are all developing into solid NHLers.
His Euro signings are literally like extra mid round picks, Borgman, Rosen, Par, Souperman, Oz, and now Barba, if he can sign someone like Souperman every few seasons, that’s literally an extra top 20 picks every few years.
Trade, beside the Kadri trade, all his trades are pretty good and he wasted no assets. I am not going to mention the Zai, Leivo and Marleau trades as those trades are made to to their own reasons.
Signings, he signed JT. He didn’t get AM the terms but it could be blessing in disguise as AM next contract will be two yrs sooner than McDavid’s renewal. Willie’s contract is fine even when he signed it. While Marner is being paid about a mil more than he should. As long as they produce, that’s all it matters. The contracts to AJ, Kap, Kerfoot, Engvall, and Muzzin are all great.
Signings UFA, I think Spezza will be first of many TO boys to come home on a min contract to fulfill their dreams of playing for the Leafs. And Spezza is doing a great job of promoting that.
Overall, I think Dubas is doing as good a job as GM as he could. Like all players, they won’t consider great till they lead their team to Championships.