Not winning the cup but this is what they do when Dermott and Hyman are back. No trades needed

Who is to stop them? The west is super weak, Boston is old and Tampa isn’t even close to signing point, the team and point are almost $2 million apart in contract negotiations.

I'd evaluate the chances of the Leafs winning the cup as 1 in 31. If they make the playoffs, I'd say their chances increase to 1 in 16.

Lol at the west is super weak, is that why Boston lost in the finals?
To answer your question
From the East:
Boston (again as usual)
Tampa (even without Point, not sure if you noticed the 28 point lead in the regular season)
Washington
Carolina
Pittsburgh (their center depth and defense are basically mirror images right now)
Philadelphia
Florida (had 2 issues last year and solved both this summer)

From the West:
St. Louis (you know just won the cup and didn't loose a single person from their roster)
Colorado (that first line is better than Bostons and they just made their 2nd line strong too)
Nashville
Dallas
Winnipeg (maybe? Depends on if they fill their holes)
Calgary
Vegas (do you know how much of a difference Stone made?)
San Jose (Karlsson's considered to have had a down year last year and still put of 45 points in 53 games)

All of these teams are perfectly capable of beating the Leafs. Their defense is still subpar and they are running and you have them on a 21 man roster, that means your 21st person has to be able to play both defense and forward in case an injury occurs.

Agree. I think Toronto is a top 10 team but not a top 5. Boston, Tampa, Dallas, Nashville, are all without a doubt more solid all around teams. You can argue Vegas, Colorado, Carolina, Pit, along with Toronto as the next grouping.

I don't think San Jose is all that and Winnepeg will have problems. Florida is interesting...very hard team to predict.

Toronto's biggest issue is obviously defense but additionally if you don't have 1 standout goalie and a very solid backup you aren't going to win a cup or even get to the conference finals. Toronto's game last year was to be okay giving up a lot of goals but to just score a more...that isn't a good playoff strategy and certainly not a cup winning strategy. May work in the regular season but not deep into the playoffs.

Defence goaltending and no toughness. Lucky to make it out of first round