He went straight from Calgary GM, to Toronto GM - meaning it's reasonable to expect that he would have been aware of the landscape of the league, and what teams were thinking.
Let's stop pretending he'd been out of work for 5 years and needed some time to get upto speed.
Again - a ridiculous notion. If he was trying, and willing, to move Nylander, he was able to move Marner.
Friedman said they had Nylander out there, looking for a Dman - they didn't like the offers, so they went the extension route.
Fact that he was willing to move on, but not the other despite the NMC looming, is remarkably shortsighted. He had the opportunity to do so, and we need to stop pretending like he didn't