all of these trades heavily favor the habs.

add your 2023 first and leafs consider

What would you prefer as your center line:

Matthews
Tavares
Kerfoot

or

Matthews
Tavares
Monahan?

Monahan will be the 3rd best center available after Horvat and Toews. The 3rd best player at something doesn't get 1st round picks at the deadline. The market is too strong for this kind of return on him.

The leafs main issue is not centers. I don't even think Kerfoot has been their 3C. If I was a leafs fan (which I am not), I would rather have my first used for something my team actually needed.

He's just stirring the pot.

Horvat is going to be priced too high for most team if he even does reach the market, and theres more than two teams looking to add a center so yes the 3rd best player available (if that ends up being the case) can certainly land a 1st rounder.

Not really. The Oilers have been after Anderson for a long time now, Puljujarvi is dead weight on their roster and no team wanted him.

Dvorak went for a 1st and a 2nd last year and is still a cost-controlled, young 3C.

Monahan allows the Leafs ample center depth at just over $1M more in cap than what Holl was making.

Dadonov at 50% for a 6th round pick is nowhere near a "steal" for the Habs.

Suzuki has fallen out of favour with Carolina, a 3rd and 4th is a very reasonable return.

Drouin to Washington for Brown (rest of the season on LTIR) and a 4th isn't unreasonable.

Edmundson is quite valuable and he might even be able to fetch two 2nds.

Finally, Blais for a 7th is a nothing deal.

There's something to consider here about cap hit as well. And how far the drop-off in available center talent is after Monahan.
Horvat at 50% retention would undoubtedly be the best, but he will go with an extension in place, very unlikely he's a rental at all.
Toews at 50% would still require a $5.25M cap hit. I could be convinced Monahan would cost two 2nds rather than a low 1st with 50% retention, but pricing in Justin Holl's contract and I think this makes quite a bit of sense since Holl's dumb requires at least a 4th rounder.

Beyond these 3, the C market is quite thin. ROR likely not available since the Blues have been resurgent. Larkin is likely to re-sign with Detroit.

That leaves: Lars Eller, Pius Suter, Max Domi.

Anderson trade needs to have more cap coming back. Edmonton can't take on any extra.

There are lots of teams available as a 3rd to eat cap. Getting Toews down to 2.75 mil would only be a mid round pick. Dumping money as part of a trade also doesn't cost anything at the deadline. The players aren't owed much actual cash and with expiring contract, its not worth anything to the teams taking it on. If the Habs are offered the 55th overall pick and Justin Holl's contract or the 56th overall pick, they'd still take the 55th because its the better return.

The fact remains you won't find many examples of 1 position getting 3 1st round picks at a deadline and Monahan isn't the kind of name that moves the needle on this. History tells us this won't happen despite how much Habs fans want it. The main problem isn't how many teams are looking for a center, it's how many teams are willing to move a 1st round pick for one. There are not often 3 in that category and especially not for someone who doesn't have a game changing impact. To put it into context, the most 1st round picks moved leading up to a deadline in the last decade has been 6. You want 3 moved for centers here(Horvat, Toews, Monahan), there are 5-7 teams who will tell you their defensemen are getting 1(Klingberg, Dumba, Orlov, Gostisbehere, Gavrikov, Jensen, Zub, since were in a Habs AGM I'll add Edmundson here too, etc), a few more who will tell you their wingers(Kane, etc). There aren't enough 1sts to go around and Monahan is likely to be one who doesn't match up to the demand. Keep in mind this is expected to be the best and deepest draft since 2015 too and those 1st round picks will be worth a premium. Everyone on CapFriendly wants 1sts for their guys around this time of year and there simply aren't enough teams willing to move them. Monahan isn't going to be the player who jumps to the top of the list of players who return one.

Suzuki for a 2nd and 4th in 2023 and Canes accept.

The three-team trades that come to mind are:

1) David Savard: cost the Lightning a 1st and 3rd (went to CBJ) and a 4th to DET for being the 3rd team retaining salary
2) Nick Foligno: cost Toronto a 1st and 4th (went to CBJ) and a 4th to SJ for being the 3rd team retaining salary

So an additional 4th round pick for retaining is the additional cost for around $1M in retention.

Toews would require around $2.5M in retention, so I'd say an additional 2nd at that point.

Monahan could fetch a 1st under the correct circumstances. He's playing over 17 minutes once again, on a 55 point pace (the majority of his points coming at even strength so no PP leverage here). He's having a fine resurgent season, the kind that would make him extra valuable as a 3C on a contending team. If not a low 1st round pick, then the same value as that (two 2nds).

When you have to start talking about the correct circumstances, you know the player isn't likely to get a 1st.

Poor argument.

Well you didn't address my other ones, so you get what you get.