All GM's are under pressure at TDL so that is poor defense of him "He was under pressure to win"
The playoff team GM's with regard to getting right pieces to contend while loser teams GM's are under pressure to maximize value of assets they are moving
If you look at most TDL trades, they're failures b/c rentals who go to new teams often fail to mesh quickly enough to make a difference, then they're gone with the assets that were traded for them. Which is why the best TDL moves are usually low cost patches which can be written off if they don't work but make you look like a genius when they do.
Caps: Mantha for Vrana, 2021 1st, 2022 2nd, Ponik
Car: Bennett & 6th for 2021 2nd, Heineman
VGK: Janmark, for 2021 2nd, 2022 3rd
Bruins: Hall for 2021 2nd, Bjork
Tor: Foligno for 2021 1st, 2022 4th
TB: Savard for 2021st, 2022 3rd, 2021 4th
NYI: Palmieri & Zajac for 2021 1st, 2022 4th
All the bigger trades included retained salary, upping the ante.
The trades involving 3rd rd picks or so probably had a big of an impact:
Pen: Carter for 3rd, 4th
Mon: Staal for 3rd and 5th
Col: Nemeth for 4th
Tor: Noeseon for 4th
Boston: Reilly for 3rd
Car: Montour for 3rd