He was a pushover in the Nylander negotiation when Nylander held out to Dec 1. Larkin, Pasta, and Ehlers good comparables, but he gave in and Nylander at the time did not merit to be paid more than any of the players mentioned, he then put up a 27 pt season off of that contract. That was the biggest Dubas mistake because it set the table for other team unfriendly contracts. You can also criticize him moving on Kadri, Hyman, Brown, Bozak, amongst many too numerous to list here, some that have gone on to cups or cup finals as valuable support players. Not to mention him trading high picks for Nick Foligno types. Or his fascination with acquiring subpar goalies. Lots to chose here, he was an awful GM in Toronto, and probably still is an awful GM/President. Don't respect him much, tried to an end around on another dummy Shanahan. Not a fan of backstabbers even if the one being backstabbed is the politician Shanahan who one can say is the architect of the Dubas charade as a NHL Exec.
Agreed. People with hindsight say the Nylander contract wasn't overpaid - it was though. Comparables at the time signed either for way less, or for less AND longer.
In terms of his tenure overall... Think about his five best moves and his five worst moves, I struggle to come up with 5 really solid good moves, but can easily come up with 5+ bad ones.
Five Best Moves:
-Signing Brodie
-Signing Bunting for cheap
-1st + 2nd + Anderson for McCabe (50% retention) + Lafferty
-Schenn for a 3rd
-Dumping Zaitsev for one year or Ceci (cost Connor Brown)
Five Worst Moves (hard to come up with just 5, so take your pick):
-Kadri for Barrie + Kerfoot
-Marchment for Malgin (obsession with "skill" over size)
-1st + two 4ths for Foligno
-1st to move ONE year of Marleau (turned into Seth Jarvis, exactly the type of cheap ELC impact player we could have used)
-Big Four contracts (which are arguably four separate mistakes)
-Mrazek contract
-Protecting Holl over McCann in the expansion draft
-Letting Hyman walk when he wanted to stay
-Will stop here, but there are more (eg Murray, not firing Keefe, not shaking up the Core Four, etc)
Even some moves that are generally praised (eg acquiring Muzzin, acquiring Campbell, moving Zaitsev, etc), he gave up good value for, so I wouldn't say they were slam dunk good moves. Like Muzzin cost a 1st + Durzi (who has become a young top 4 RHD) + Grundstrom. Campbell cost Trevor Moore and a 3rd, and ultimately struggled for us when it counted and got us nowhere. Moving Zaitsev cost Connor Brown.