If Nylander's camp is dug in at an unreasonable number as speculated, I'm not sure how anyone could fault Dubas. If he caves in at the 11th hour and overpays Nylander or he makes a trade out of desperation for less than an equitable return, that would be the worst case scenario for the Leafs in my opinion.
The Leafs are not struggling without Nylander. If he is not willing to come terms on a reasonable offer, not only does it jeopardize the Leafs cap situation, it lowers his trade value as well. If he thinks he's worth that much, let him sit out as far as I'm concerned.