You know what?
I have been vocal in the past about how much I hate loading up at the deadline. It was clearly a waste of assets when Dubas was in charge as evident in the postseason, and we have a skin-deep roster and prospect pool with no success to show for it as a result. I hate rentals, most of the time; it's often (but not always) a sign of "we didn't prepare well enough in the offseason to fill the holes in our team" or something. Since winning the Cup also involves quite a bit of luck, it's usually a fool's errand to sell your soul for a year, and cap teams always need cheap, ELC talent (best acquired through the draft, obviously) to plug holes that are created when players they can no longer afford leave in free agency.
This year, they are getting better goaltending and generally playing a style more conducive to the postseason. They need to address the 3rd line center issue and find a good shot from the point on the PP so that teams are forced to give guys like #34 more space (this is so badly needed because while guys like Rielly can move the puck you can play off him since he's no real threat to shoot.) Pending Auston's health, this team has a shot of doing something if, and only if, the core finally understands and accepts what it takes to win and delivers like they hypothetically could. I personally am not holding my breath because I don't think these guys truly get it, but reading nothing but negativity all the time is exhausting so I'm attempting to be constructive here.
If, after loading up, the Leafs *still* lose in the 1st round of the playoffs then there's no need to fret in the first place because...that's it, that's the end. There's nothing further that could be done with the team's existing structure and really the whole entire thing would need to be nuked from orbit, starting with a removal of Shanahan and letting Marner and Tavares either sign elsewhere or have their rights traded if possible to recoup a tiny something. If we load up at the deadline and they still bow out early, they'll truly *never, ever* get it and it's time to turn the page, assuming that point hasn't already occurred. Mitch and JT are on expiring contracts, either you win this year or you blow up the core, there is no in-between, you've given the big 4 more than enough chances at that point and you have to move on as urgently and aggressively as possible. If they lose in the 1st round yet again after loading up then you unequivocally need more than a retool, you need a full rebuild. Period.
This year is your best shot. Kill or be killed.