Quoting: Juice
I think they would have to wait for Jan. 1, 2019 to sign another extension. The AAV on that extension wouldn't theoretically apply until the 19-20 season.
I mean, it's not a realistic scenario but I like the line of thinking
Thanks! Cool.... So..... but that next extension, it can be another eight years? Do the Leafs, in January, recoup any further cap savings for writing an extension at say, 40 over 8, for a total of 50 over 9? Obviously a couple guys like Marleau are still getting contracts into their mid thirties with high dollar amounts, but there's also something to be said for looking at the average lengths of careers of top six wingers in the NHL. It's a dangerous job. Having an extra couple million might be worth lowering the cap a bit. But while we're totally ignoring reality, why are we leaving the Leafs with 6M in wasted cap space. I mean, how about a one year 16M deal, in exchange for agreeing to an extension at 4x8? I think the CBA pretty clearly was a response to an offersheet on Fedorov that used this kind of math, but I wonder whether it actually says anything about players signing with the team that already controls their rights. There's obviously no obligation to make long term plans. If the Leafs offer a one year8M deal and then extend him at 6M, it's hard to say if he's taking a hometown discount out of loyalty or just because he sees the value in long term security.
Of course, as a Caps fan, I should point out that there are plenty of teams that would love to welcome Nylander with open arms if he ever does decide to pursue unrestricted free agency, but for the enjoyment of the exercise in salary cap logic, I woudn't doubt that this happens all the time, if one looks back far enough. Players' contract values go up and down, and it's pretty hard to tell how any of the amounts make sense when games are fun to play, and, if money weren't an issue, we'd all play hockey for free, quite happily.