Joined: Aug. 2018
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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.