One simply doesn’t trade a pick like thy Alexis Lafreniere!

1 to 5 in value is probably similar to this, though OTT would decline. This is a "bot teams say no" type of thing

This

You can bet your rear end that IF the Leafs somehow fell into the #1 pick this draft, and you can sure bet it would come with its hardship of losing to Columbus in the play-in round, which perhaps is a discussion for a different time and what changes to the Leafs might looking following such a blow, they will not deal such an elite player, nevermind prospect, to someone in their own division.

The real question you need to ask yourself is, which team would be desperate enough to make the Leafs an offer they couldn't refuse? If the Oilers lost the play-in round, I could see them pretty desperate. Would the Wild or Ducks be desperate enough? Not sure. It would take several significant pieces, but based on where the Leafs are at at that point, I think the Leafs draft the pick.

Doubt Ottawa would make that trade, but I don't understand why you'd be willing to make that trade from Leafs perspective. Tkachuk needs an extension after next season, while AL will have two more ELC years. Given the uncertainty of the caplimit for the next few years, that ELC contract is even more valuable

Good point.