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2025 Offseason Thread: Spring Cleaning

2020-2021 - Toronto chooses Wayne Simmonds over Corey Perry
- Perry accidentally concusses John Tavares
- Wayne Simmonds puts up 0G 1 A in 9 playoff games as a Leaf. He scores 12 G 15A over 128 GP
- Corey Perry has 21G 20A 41P in 88 playoff games.

This franchise consistently botches the bottom 6.
To a certain extent I'm sure all teams have stuff like this but yeah it's kind of stunning looking back and thinking about all these little mistakes.

Like Mike Amadio gets waived by the Leafs a month into the season in 21/22 where he played just 3 games for the team. Next season he's winning the Cup with Vegas while scoring 5 goals in 16 games in a 4th line role (as a fun reminder 34+16 combined for 5 goals in 13 games each this run).

One weird misstep that I never got was why Evan Rodrigues never played here. He was a part of the trade that sent Kapanen to Pittsburgh in 2020. At the time was a pending RFA who was due a $2mil qualifying offer which was admittedly pretty high at the time for him so the expectation was neither Pittsburgh nor the Leafs were going to qualify him at that amount. But he was a Toronto born player so I guess the hope from us was that he would be willing to sign an extension for less than his QO. That didn't happen and he ended up going right back to Pittsburgh on a measly 1-year, $700k contract. He bounces around PIT, COL, and FLA as a 40-point guy and eventually wins the Cup last year.
 
Brown, Hyman, and Bunting were all core 4 cap casualties. You cannot have a supporting cast paying four forwards $+11M. I don't know why anyone would expect anything more than what the Leafs are getting from their bottom 6.
 
Brown, Hyman, and Bunting were all core 4 cap casualties. You cannot have a supporting cast paying four forwards $+11M. I don't know why anyone would expect anything more than what the Leafs are getting from their bottom 6.

I’d argue they were moreso flat cap casualties, as all or a couple of them would have likely been re-signed had the cap not gone unprecedentedly flat for years on end.

The salary cap increased between 2023-24 and 2024-25 by more than it did between the entirety of 2018-19 and 2023-24. No discussion of the core 4 or cap room or whatever can be accurate without acknowledging this point.
 
To a certain extent I'm sure all teams have stuff like this but yeah it's kind of stunning looking back and thinking about all these little mistakes.

Like Mike Amadio gets waived by the Leafs a month into the season in 21/22 where he played just 3 games for the team. Next season he's winning the Cup with Vegas while scoring 5 goals in 16 games in a 4th line role (as a fun reminder 34+16 combined for 5 goals in 13 games each this run).

One weird misstep that I never got was why Evan Rodrigues never played here. He was a part of the trade that sent Kapanen to Pittsburgh in 2020. At the time was a pending RFA who was due a $2mil qualifying offer which was admittedly pretty high at the time for him so the expectation was neither Pittsburgh nor the Leafs were going to qualify him at that amount. But he was a Toronto born player so I guess the hope from us was that he would be willing to sign an extension for less than his QO. That didn't happen and he ended up going right back to Pittsburgh on a measly 1-year, $700k contract. He bounces around PIT, COL, and FLA as a 40-point guy and eventually wins the Cup last year.

At the time I think it was Mirtle said the Leafs and Rodrigues couldn’t agree on a number so presumably he was looking for more from the Leafs, otherwise they would have had him signed had it been for that amount.
 
I’d argue they were moreso flat cap casualties, as all or a couple of them would have likely been re-signed had the cap not gone unprecedentedly flat for years on end.

The salary cap increased between 2023-24 and 2024-25 by more than it did between the entirety of 2018-19 and 2023-24. No discussion of the core 4 or cap room or whatever can be accurate without acknowledging this point.
How is it that only the Leafs screwed this up?
 
I mean, you could probably build a pretty good hockey team with all the players/picks/prospects the Leafs have frittered away.

Carter Verhaeghe to me was a big "meh" when the Leafs traded him for Grabner.

Seems like patience is short in Leaf Land.
 
Shea Theodore and William Karlsson is who I’d start asking for too
Karlsson would be an interesting one to revisit this offseason. Coming off a down year, Knights might want to move him for cheap just to clear cap space. Heck maybe even reunite him with one or both of the original Misfits line with Marchessault and/or Reilly Smith.
 
Karlsson would be an interesting one to revisit this offseason. Coming off a down year, Knights might want to move him for cheap just to clear cap space. Heck maybe even reunite him with one or both of the original Misfits line with Marchessault and/or Reilly Smith.

If Vegas wins the Marner bid, they will need to clear space, and the Leafs can make a play here (or whichever of Florida/Dallas etc signs Marner). I toyed with a Reilly Smith - William Karlsson - William Nylander line 2 for funsies.

I suspect Vegas might LTIR Pietrangelo instead
 
How is it that only the Leafs screwed this up?

I don’t know, did any other teams sign four highly paid players like the Leafs did between July 1, 2018 and Sept 13, 2019 -aka the last one being signed 6 months before the league shut down due to the pandemic. You could not have it happen any worse for the Leafs. All of these contracts would have been signed with cap projections going forward, projections which were assumed to give them wiggle room to maneuver.

Put another way, in the 5 seasons prior to and up to 2018-19, the cap went up by 15.2 million. In the 5 seasons after (aka immediately after they signed all of these deals) the cap went up $4 million.

How much different do you think everything looks if the cap continued to go the way it had before? There was NO WAY to predict the global pandemic at the time these deals were signed, and yes IMO, it uniquely affected the Leafs (doesn’t mean it didn’t affect others too).
 

1. Danault: I've wondered if the Kings would look to shop Danault as well. New GM, Byfield's game/role/responsibility is increasing, and they might need to clear cap space for a big swing (Marner). With that said I couldn't possibly imagine the Leafs have the trade assets to make this deal anymore.

2. Kadri: If the Flames wanted to mostly ditch his contract (and let go of their dumb beef with Treliving) I'd certainly be interested. But I doubt they'd give him away for cheap because honestly if he was a UFA I don't think getting 4 years x $7mil would be that out of the question so probably not happening with our lack of resources.

3. Karlsson: Liked him last offseason, might be cheaper to get this offseason. Definitely a solid option.

4. ROR: I think the ship has sailed here. And also as much as I like the player I want to get faster down the middle, not slower.

5. Pageau: Pumped his tires a lot last offseason, but he rebounded recently so I expect the Islanders wouldn't be looking to just give him away anymore. He'd be a great fit for 3C at the right price but I also think a somewhat lower ceiling guy like him only makes sense if we get a new 2C while Tavares moves to the wing full time.

6. Schenn: In hindsight it might be worth debating if the Leafs should have taken the Minten+1st from the Laughton deal and tried to make that plus an extra piece or two work to get Schenn instead. But that ship has sailed too and the assets to make a deal like that work are long gone.

7. Wennberg: Probably similar to Pageau in that sense that this would only be ideal if someone like Karlsson was also acquired to push Tavares to centre.

8. Zacha: Again, in hindsight, maybe the deadline play should have been to try and get either Zacha (or Coyle) alongside Carlo instead of Scott Laughton. At the time though I guess it likely wouldn't have worked cap space wise. Regardless the ship has sailed and I don't see us having the resources to make an attractive trade offer here.

9. Zibanejad: They don't directly steal my Zibanejad for Rielly trade proposal but he makes the list anyway. He might be my top target assuming the Leafs don't use up a ton of their cap space on Bennett (and it's sounding more and more likely they won't even get a chance to offer I think). Likely available for pennies on the dollar considering his contract. If he rebounds he's basically the perfect 2C to fit between Matthews and Tavares. If he doesn't rebound well we probably would have lost in the playoffs regardless so what's the point of any of this anyway really. Biggest hurdle is probably his NMC but perhaps Nylander can sell him on the idea of playing here.
 
I want to get faster down the middle, not slower

This is basically what matters most.

I think Tavares can still swing it in a 3C role with some smushers on his wing.

For 2C, aside from the aforementioned William Karlsson...

The Avalanche are up against the cap: some options to pull from them might be Ross Colton or Charlie Coyle, or even Martin Necas who apparently isn't happy anywhere he goes.
 
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