Okay. JMO.
FYI, if Toronto signs Nylander to a 2 yr bridge contract that will get the team to the 2020-21 season before you have to sign him again. At the end of the 2019-2020 season Marleau's $6.25 mil contract comes off the books and Mathews and Marner will already have signed contracts. A 2 year bridge contract gives the team a lot more flexability and certainty with regards to the salary cap. Nothing wrong with doing a bridge deal. Its not like Nylander is the cornerstone of the franchise's future.
If that happens and Nylander adds PP production to his great ES production, and the cap keeps going up, the next contract will start with a $9 AAV. Long term, the Leafs are better off potentially saving $3 million a season long term than saving $2 million short-term.
Who said he's the cornerstone of the franchise's future? Do you know what those type of players get coming off of their ELCS now? Between $10 and $12.5 million (see Eichel and McDavid and see Matthews soon). Most are suggesting signing Nylander to around $6-$7 million AAV longterm, in the range of Ehlers and Pasta.
The only players better than Nylander (in their ELC years) that I recall getting bridged recently are Subban and Kucherov. Montreal could have gotten Subban on a cap-friendly deal long term, bridged him instead, and ended up having to give him $9 million a year in 2014 (with cap inflation that close to $11 million). Tampa bridged Kucherov at just under $5, what is he going to demand in his next deal?
That's very little savings short-term. He doesn't have recent comparables, even including cap inflation, that justify anything north of $7 million a year long term. Why not just give him $6.5-$7 million long-term instead of $5.5-$6 million short and then, potentially, a big number after.