Actually it's probably their second worst. Toronto has struggled ginding against physical teams in the playoffs recently.
We also saw similar problems faced by Tampa.
Only team I think that would be worse for the leafs in the Canadian division is the Jets as I feel like they are a better version of the Habs the same way the leafs are a better version of the Oilers.
Hilarious that you are conflating the Habs "grinding" game with that of prime Boston, Washington, and Columbus. All three of those teams were some of the heaviest clubs in the league with top notch coaching/systems. MTL has nothing close to Werenski-Jones or Chara-McAvoy and Ducharme is clueless.
The Habs are a homeless version of those teams. The Leafs were also overwhelming underdogs in 3/4 of those series, yet they "struggled" to take the favourites to 7 games, down to the wire. Not to mention this Leafs team is way more built for a dog fight of a series. Simmonds, Foligno, Bogosian, Muzzin, Holl, Hyman, Thornton, Noesen, etc. can hang in there physically with anything in the division.