he was pretty specific in saying he doesn't want a bridge deal

The situation has evolved, according to rumors which are backed by the public pronouncements by the Leafs and then Nylander's personal reply.

Dubas is now forced into a short term deal, having first listened to trade proposals and then waiting for Nylander's camp to cave in.
Because it's now public Nylander will sign an offer sheet if Dubas doesn't put something new in front of him: short term or high price, pick one.

Take a small loss, then trade when the time is right. Dubas did want to retain Nylander long term, but he is a kid that hasn't stood up to Shanahan and Babcock even though he'll now own their mistakes.

It will be a very interesting season to watch Dubas. Leafs, Panthers, Coyotes all brought in young analytics minded GMs, who inherited a tonne of great pieces and are just now starting to succeed or fail based upon the choices they make. If Dubas is smart he'll show Shanny a video of Melnyk, and then tell him to stfu about anything important to the roster unless he wants to be remembered the same way.

lets see what happens. this was only the beginning. u still got marner and matthews to deal with it lol. as for shanahan, he took hefty shots at nylander and future contract signings. and idk if u read matthews reply to a pay cut, but his response was basically "yeah, thats a no from me dawg" (he didnt actually say that). as for analytics, imo, there needs to be a balance. like we saw in florida a few years back with tallon stepping down and team becoming a disaster.

" So he'll be traded to a team that can afford to pay him". I don't think it means that at all. Are you saying all RFAs can "hold out" and wait to traded to a team pay him the most?
The non signing of Nylander has nothing to do with the Leafs not being able to afford him, it has everything to do with Nylander and the Leafs not being able to agree to a contract for term/salary.

If Dubas was in position to freeze Nylander out, the whole situation would be in the distant background as all GMs/agents/media knew the real story and respected it.
That's what I believed to be the case before this week. Maybe 6 years instead of 8, maybe closer to $7 than $6 but a negotiated compromise.

Everyone is being polite for now. If Nylander signs an offer-sheet in November, it will be seen as Dubas' fault and no one will back him up.
Shanahan tried to pressure Nylander and came out looking like a hypocrite, and Nylander came out looking better than before with his reply.
The pressure, because it's clear this won't quietly remain in the background, is now on Dubas who has to take the one way out to defend against an offer-sheet.

There is conflict within MLSE that is inhibiting planning. Recall that effectively Komarov, JVR, Bozak, and Plekanec were rental players for a team that lost in the first round.
On the one hand they're fine this season, on the other hand they need to be of one mind so that they can be flexible in the timing of contracts or have backup plans prepared if their first choice is denied.

People don't want to hear it but Shanahan has a terrible reputation among teammates and NHLPA he betrayed out of pure selfishness. Babcock is good and bad (hear out Mike Commodore on Spittin Chiclets, mandatory listening), but he is definitely untouchable and Dubas will have to work around him even though he won the GM job.

All I'm saying is don't confuse the rise over the last few years with talent across the board, and the next couple years will be far more revealing as to who's putting the shine on and who is actually earning their money.

You really should lighten up dude, the world isn't falling into darkness. Nylander wants to be a Leaf and the Leafs want him, just take a deep breath and enjoy watching Matthews and Tavares destroy everyone.