This is why Nylander is obvious choice to be moved
I think the minute they signed Tavares it became an either/or proposition between keeping either Marner or Nylander for cap reasons going forward, if the goal was cup competitiveness.
This required foresight and not hindsight to have the best possible outcome here.. Unfortunately those in power had to first see this play out as it has, and now are in a reactionary position as opposed to proactively handling this, as we witness escalating salaries put pressure on decisons.
Last year while Nylander was still unsigned and names like RHD like Parayko and Werenski were mentioned in trade rumours and upgrading the Defense was a possibility, that was the time to strike knowing that Matthews and Marner would join JT up at the top of the Leafs salary scale, and the $7 mil you were going to have to pay Nylander would be better served as a significant upgrade to the dcore and better cap management for the Leafs.
Do we really need Leafs signing or matching an OS for Marner to realize that it might very well result in missed playoffs, because this is uncharted territory of paying 4 forwards nearly 1/2 you cap and the impact on the rest of the team might result in failure and not success.
Hopefully we're not sitting here a year from now after having missed the playoffs that finally now realizing that saying "We can and We will" sign and keep all 3 kids and needed to be proven wrong first to force change, because then it will be obvious that was once hoped for was not realistic and you've wasted more "Cup windows" getting to the same conclusion.