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What would it take to move the 1OA pick?

You also realize by getting an established player you're likely losing 5-7 years as that player will likely be 24+ years old. It's the Kessel falacy again but sub a defenceman for Kessel in this case.
 
You also realize by getting an established player you're likely losing 5-7 years as that player will likely be 24+ years old. It's the Kessel falacy again but sub a defenceman for Kessel in this case.
But Kessel came to a team where he was pretty much the only guy. A 24+ year old 1D would be complementing 2 of most talented players the franchise has ever had.
 
But Kessel came to a team where he was pretty much the only guy. A 24+ year old 1D would be complementing 2 of most talented players the franchise has ever had.
That maybe you only get 2-4 years out of depending on contract and UFA status.

And keep in mind I'm not talking about Kessel as a player here - I'm just using this as an analogy.
 
That maybe you only get 2-4 years out of depending on contract and UFA status.
I mean, if it doesn't happen in that window, they're rebuilding anyway.

I think there are three paths: keep McKenna and trade Matthews, Nylander, etc to get the rebuild going; trade McKenna to contend now; keep McKenna and the rest to recreate that 2018-2025 magic. #1 might be smartest, but it isn't happening with the team's ownership.
 
Okay, I feel like I want to jump in here. I will do my best to stay level headed and not get crazy, so that I don't annoy people and get asked to leave.

There are bad scenarios in this no matter what you do. If you keep the pick, it is possible that McKenna is more Alexis Lafrenière than Macklin Celebrini or Connor Bedard.

You could trade the pick, pick up some assets. But then McKenna could be off the charts good and you passed up on that prospect.

They do need a #1 defenceman and they need a path forward there. They also probably need another good centerman, more than they need a talented winger. Winning the first overall pick is awesome, but it is unfortunate that it happened in a year where the first pick is not really what they are looking for.

My problem is that I don't trust this management team, so no matter what direction they go in, it will color it, for me at least, towards the negative. It will take some time for the management team to gain my trust. I've just been burnt too many times over the years, and this one looks like one of those times Leaf fans are gonna get burned.

Personally I will need to see decisions that are made that seem like coherent competent decisions. I guess in this case you keep the pick. You might be able to sell me on a trade where you flip the pick with Vancouver and pick up Pettersson at the same time. You'd really have to hope though that Mats could bring Pettersson back to what he was before, so I would probably still have reservations.
 
That's why you trade for picks and accelerate a rebuild.

My only problem with that is whatever team trades a 1st round pick as a return for a Matthews or a Nylander is not (probably) going to be a high pick. It will probably be a later round 1st round pick as the teams Nylander or Matthews go to will be going for it.

Rebuild in 2 years when you have your 1st round picks if you need to go that route. McKenna will still be young.
 
I mean, if it doesn't happen in that window, they're rebuilding anyway.

I think there are three paths: keep McKenna and trade Matthews, Nylander, etc to get the rebuild going; trade McKenna to contend now; keep McKenna and the rest to recreate that 2018-2025 magic. #1 might be smartest, but it isn't happening with the team's ownership.
That could change but maybe not before the draft.
I would be pressing Matthews about his alleged position about not playing for the Leafs next season or what his position really is.
If Matthews wants out, Nylander, like Matthews, doesn't want to hang around for a rebuild.

Effectively, Matthews is the Leafs GM until he settles on his future. Because his decision will probably decide the direction they take.
To me, the heavy odds are Matthews agent and hockey buddies are telling him this team will not be a Cup contender any time soon - particularly if they're in the camp doubting Chayka's ability. If Matthews wants to win a Cup in the next few years while he's close to his prime, he probably needs to find another NHL team to do it with to give him a decent chance.
Once he figures that out, if he hasn't already, then the direction the Leafs should go will be clear.

Those drafted below the top 10 or so typically take between 3-5 years to become NHL regulars. Right now, after this year, it will be 3 more years before the Leafs might get a top 10 pick - but they'll have to be a lousy team for Matthews to get it. There is little help coming for Matthews trying to win a Cup here from the drafting and development side of this franchise. UFA market with increased cap space might be brutal like it has been in recent years.

Realistically, in the short term, all the Leafs can probably offer Matthews is improvement to get them back into the playoffs. As nearly everyone from the 28th place team is signed for next season, it won't be easy to dump the contracts of those they don't like/want anymore. Burning more draft assets to move them snuffs out the retooling. They're in a tough spot and there's no quick fix to contending for a Cup.
 
You don't. I think you pivot to getting a lot younger, recouping assets and getting more picks. If Matthews is unsure if he wants to be here he should be traded.

I might explore trading down to draft a D but by all accounts Stenberg and McKenna are a tier above.
 
I would do a deal similar to this one:

The trade: The Flyers trade Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, $15 million, and two first-round picks to the Nordiques for the no. 1 pick.

Player taken: Eric Lindros

Leafs can skip the 15mi... but yeah this kind of ransom you do the trade, and that trade work very well.
 
My only problem with that is whatever team trades a 1st round pick as a return for a Matthews or a Nylander is not (probably) going to be a high pick. It will probably be a later round 1st round pick as the teams Nylander or Matthews go to will be going for it.

Rebuild in 2 years when you have your 1st round picks if you need to go that route. McKenna will still be young.
Like CW said, force Matthews to make his call now and get on with it. Watching him walk would be a ridiculous thing for a floundering team to do. What could the Leafs possibly do to be a legit contender over the next two years?

A Tanev/Woll/Stolarz repeat of 24/25 is not happening.
 
And we are talking about Mckenna all the time, what if they draft Stenberg as #1 ? how would you feel ? (see Matthews x Laine all over again)
 
I would do a deal similar to this one:

The trade: The Flyers trade Peter Forsberg, Ron Hextall, Steve Duchesne, Kerry Huffman, Mike Ricci, $15 million, and two first-round picks to the Nordiques for the no. 1 pick.

Player taken: Eric Lindros

Leafs can skip the 15mi... but yeah this kind of ransom you do the trade, and that trade work very well.
For sure - except this kind of trade will never happen again.
 
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