Might as well wait until Matthews hits the UFA market in 2024.

Think of it as he is willing to sign an extension with the right team and we don't want to miss out.

what an awful trade for the leafs, not a single thing remotly close enough to be a centerpiece for Nylander let alone Matthews and then you throw in that horrific couturier contract like it has value?
Brutal

because Matthews is totally gonna sign in Toronto

Matthews isn't signing with Philly, Nor is Karlsson waiving to go to Philly when he wants to play for a contender.

There is a reason I added the condition to the 2nd...If Couts doesn't play a lot you then get 2 1sts, TK (who is worth more than a 1st by himself) and a prospect who projects to be a top 6F. If Coots does play, then you get a Selke winner who will get 70ish points and the rest of what I listed.

It's actually excessive imo.

But you enjoy your final season of Matthews.

Even if he won't, I'd rather take one last run than take that return

yeah, it's not like literally every superstar that was with the team who drafted them at the end of their 2nd contract has re-signed with that team except the one guy who signed in....oh he signed in Toronto. Weird
the leafs should totally trade matthews for a horrific return because of that

Leafs would rather cash in then let him walk

I think if you add Bedard and Matthews, this team becomes a playoff team immediately and anything can happen in the playoffs, unless you are the Leafs then we all know what happens.

This isn't cashing in

Couts turns 31 like 90 days into next season and is signed until he's 37 with significant health worries. He is a massive massive massive risk and hasnt gotten close to his selke calibre in the two years since.
He's not a piece to get matthews

Philly is currently 7th OA, Bedard is a major pipedream. Very rarely do teams who finish 7th OA ever get the number 1 spot. You've a greater chance of staying at 7 then you do getting the top spot.

if they're looking to cash in, then they'd need a significantly better return than this

getting more then you would next off season...

It's almost like I labelled this "Pipe dream" or something...

Overall I like it, but Matthews (if Leafs dont play for the cup this yr or next, hes not resigning for so little, and the leafs cant really trade him in-season 23-24, but maybe his negotiating rights following 23-24 season), but he either signs for a team that has won the cup or he goes for the money. I could see a PHI team with Bedard and their young core as a good location.

However, Karlsson wouldn;t be where I'd go for a top RD, although admittedly he and provorov could be a good pair.

To me, if I was in this fantasy, maybe I stick with the karlsson deal, although Frost probably weighs that too much in SJS favor. I'd hope Leafs tank out this season and then next, sign Matthews for 17mil. In the above, you have okposo eating 3mil and 9mil in cap space, pretty much about enough to keep coots and koneckny. I'd keep Couts as 3C, and either trade Koneckny for a boatload or Laughton, giving you a third line of Cates-Coots-Koneckny/Brink (not to mention Gautheir might be here by then).

Matthews will be tough:

Imagine Leafs make it to 2nd or 3rd round this year and then crash out. Do you actually think they will be bad enough in 23-24 to trade Matthews in season or at TDL, thereby just writing off the entire year?

Of course not. The Leafs will either have to deal him this off season, get an extension in place before the end of 23-24 regular season, or trade his negotiating rights in the off season of 23-24. They will be a good regular season team and couldn;t just trade their best player (and his cap hit) at deadline, right before they go into the playoffs. Think of CGY with Johnny Gaudreau.

To be fair, his negotiating rights aren;t worth tons (its a short window and youd need a team that has almost 20mil available that has upside and lots of cheap ELC), the team couldn;t implode itself at the TDL, so really its an extension at close to market value (with the cap increase in 24-25, thats probably 15mil) or they try and win it all in 23-24 and compete for him as a UFA as the defending champions.

But lacking so many picks and just a handful of top prospects, the Leafs long term outlook is not as rosy.

Make it a ‘24 2nd, and CBJ accept. We’ll even throw in Bemstrom.

I am a flyers fan and that doesn't get Matthews, doesn't even come close, if he was ever dealt you are talking something like TK, Farabee, Foerester and multiple first round picks, think the Thachuk trade + more assets. Also close to 0% chance he signs as a FA in Philly. He will go to LA or Arizona before any other team.