This might be a hunch but I don't think Holland looks at this trade

Well it is Ken Holland so you can never be sure.

The retention alone would cost at least a 5th round pick.

At this point I am not sure that can even happen. McDavid could become a leaf but not until he's FA the same time JT is off the books

Sure dude the Leafs haven't won a cup in 55+ years, And they can't get out of the first round. And even with McDavid that won't change. And acquiring McDavid would hurt Toronto more than helping them. At least both Matthews and Nylander would be out the door if not a lot more.

Both TB and Chicago have won 3 Stanley Cups since Toronto won a playoff series.come on now.

Cant wait for Mathews to leave Toronto.

While I do think McDavid will sign with the Leafs, he will starting playing for the Leafs via UFA, not via trade.

I wouldn't stop there. Good chance Matthews, Nylander as well as Tavares and may even Marner are off the books. Leafs fill lose their big names to free agency with other UFAs

sorry but mcdriveway doesn't clear kerfoot

This site has broken you

Really? I'm always amazed when CF followers think "their" team can sign any UFA they want, but get all weepy eyed when "one of theirs'' UFA leaves their team.

One of theirs leaving rarely happens. And there is zero reason to think TO is going to lose their entire core as FA's. Rielly resigned because he wants to stay here. Matthews has called TO his home. Marner talks about it's a dream to play for his childhood team. Nylander says he doesn't ever want to leave. JT took less money to come here and yet everyone is going to leave

Players very very rarely throw their themselves or the team "under the bus" by saying they want to leave. So please what players say publicly has no meaning. I'll agree with you about Reilly and Tavares. But there is no reason to be surprised if Matthews and Nylander leave, especially if the Leafs can't match the salary they get elsewhere.

They can, the Leafs have essentially no one signed beyond next season. They will do what they always do, spend big on the core and fill the rest with value.

Of course they can. But tell me if the cap goes to 89.5 in 24/25,,,,that's 7m more than now. And Matthews wants 3.5m and Nylander 2.5m. That doesn't leave room for other guys.....Sandin/Liljegren should get big raises. How about centre Holmberg and Kampf, LWers Bunting, Timmins.
I still say Matthew wants to go to big market US city. But paying Matthew and Nylander more money, doesn't make them better player than they are now. It's like the Canucks, possibly
This season Miller makes 5.25m. Paying him 8m next season doesn't make the Canucks better....or even Horvat resigns for 8m....and increase of 2.5m doesn't make the Canucks better next season.

The best example this off season was when the Flames made the Tkachuk trade. I liked the trade getting Huberneau, Weager and a 1st for Tkachuk. But the Flames made big mistake extending Hubie with almost 5m pay increase.

The difference is TO doesn't have terrible contracts filling their cap. Brodie and Muzzin are of the books and that will go to Sandin and Liljegren.