Why?

Because Holl isn't a Top 4 Dman on a Cup contender, only on a Cup pretender will you find a player of his talent in the Top 4 pairings.

Hence the Leafs need an upgrade to push Holl down to 3rd pair where he belongs.

This is true, but your forward depth is significantly worse. Holl is closer to being a #4 D than any of your forwards outside of the big 4 are to being legitimate 3rd line guys. Kampf is not a 3rd liner. Neither are Simmonds, Mikheyev, Engvall, etc. Ritchie/Bunting/Kase maybe but all do have some question marks (penalties, sample size, health) that maybprevent them from being 3rd liners. Robertson is a rookie and shouldn’t be put that high in the lineup immediately. Kerfoot is the only guaranteed 3rd liner you have, but you want rid of him for some reason. To put it another way, Mathieu Joseph was Tampa’s 11th best forward, and he’d be 6th best on the Leafs, so I’m not sure why you’d want rid of one of the 5 guys better than him, that forward depth is significantly more important.

Well it'd be interesting to compare the Leafs and Tbay within a couple years, when Tbay will be blowing $45 million on 5 players also (Kuch, Point and Vasei @ 9.5, Stammer @ 8.5 and Hedman at 8).

Easy bet is Tbay will still be better than the Tor.

As for Robertson, look at his brother in Dallas, give him a Top 6 role out of the gate.

True, if your brother is good at hockey then you are for sure ready for an impact NHL role. The Leafs should sign Griffin Reinhart to replace Holl on the 2nd pair

Nice one, do you watch hockey ? Nick is as talented as his brother.

The Stars are a better organization than the Leafs, Jason was giving a chance, the Leafs will ruin Nick by the slow approach as you suggest.

Whatever happened to Lilypad's development ?

The amount of players who can immediately jump into a top 6 NHL role is extremely small. Those that do either have a slow burn like 3+ years of pro hockey either in Europe or the AHL or are top 10 picks, neither of which apply to Robertson. Throwing him to the wolves immediately will only hurt the development of a guy they quite frankly NEED to be a good player for them for cheap for the next few years. Look at what happened to Mittelstadt in Buffalo. They tried to make him their 2C too quickly and it’s taken him 3 years to recover enough to be an NHL regular. Robertson would be much better off on the 4th line with Spezza, a veteran guy that can provide mentorship, a talented playmaker that will be able to develop his goal scoring talent at the NHL level, on a line that should be well-sheltered in terms of ozone starts and minutes. If he does well to start and earns more minutes that’s great, but pencilling him in on the top line immediately would likely be a mistake in his development and also a major red flag showing the complete lack of forward depth the Leafs have that this is even a conversation.

Yeah Im starting to suspect maybe Dermott could be moved. Especially when we consider how much dman are going for right now.

The D market has shrunk quite a bit and the only guy worth a look for us rn is Demers. That said he probs wont be getting 3 mill. Probs will see a 2 year 1.2mill deal or something.

Will have to wait and see what happens. As who knows Rielly could be moved if contract talks dont work out in August and neither guy will need to be moved