Matthews and Nylander were significantly worse are the time of the signings. Especially Matthews who absolutely bullied Dubas with that contract and changed the RFA contract dynamic in the whole league. Hainsey's contract is over and Marleau only has one year left, those are your typical vet signings (AKA nothing to see here).
Zaitsev was pretty bad but you need to remember the context here. He was a star dman in the KHL, in his prime, who just had a 36 pts first season in the NHL. They got fooled but it happens.
There's no excuse for Matthews and Nylander though. Dubas not only did a piss poor job for the Leafs but it's going to hurt everyone else.
If you're gonna tell me the worst contracts on the Leafs are the two best players (not including Marner) then I'm gonna tell you to put down the glue bag.
We always get in this mode of how one player supposedly messes up the RFA market, way back when it was the Sakic offer sheet, or Kariya, or Richards. Truth of the matter is, he's worth it as he's the best player the Leafs have had in at least a generation, if not more, and will be the primary reason they end up winning a Cup. Signing those veteran contracts didn't kill their cap, but I'd argue it didn't do much as both players were mediocre (and in some instances outright bad) this season. And what's more, Babs in his usual fashion way, way overused both players, because that's just the way he is.
And f*** context. They didn't need to sign Zaitsev to that ridiculous contract after one season. They could've done a lesser deal (but probably had to cough up a little more AAV) but that deal is a total albatross now. That was a dumb, impetuous move by Lou, who is by no means perfect. And FTR, neither is Dubas, but I certainly wouldn't characterize his first effin' season as "piss-poor."