Benning let Markstrom walk to the Flames, is now not only their bonafide starter, but is arguably a top 5 goalie in the league with the way he has played this year.
Benning let Tanev walk, again to the Flames, who has rounded out the defence and him and Hanifin as a pair are statistically one of the best pairings in the league.
Benning let Toffoli walk to Montreal and he has 9 goals and 13 points in 13 games for Montreal.
On the other hand Ken Holland has given McDavid, Archibald and Khara to play with (yes I know it's when he is double shifted, but come on). He has done more than nothing to add to a team with two different Hart winners, so much that they play the final 5+ minutes of games. 6 years into McDavid's career and his team is so shallow he has to play a near 6 minute shift because the rest of the team is so utterly pathetic.
Even though most of Bergevin's moves make no sense and he constantly seems to get fleeced, it's hard to hate when their team isn't actually that bad, they're quite good.