Quoting: palhal
He was overpaid at the time of signing of his contract. Pasterank signed that summer at 6.67 X 6. Larkin 6.1 X 5. You have to look at comparables at same time period. So Nylander for a six year term, 500,000 overpaid. At worse, it gave the precedence that the Leafs could be bullied in contract negotiations. Leafs were in first place at a 120 point pace, when he did sign in late November. I would made him sign "on team terms", wait for an offer sheet, or let him sit out the NHL for one, instead of giving in.
Comparables $$--% of cap--date of signing--1st prior--2nd prior (pts that year)
LARKIN--$6.1M--7.67%--Aug-18--63--32
EHLER--$6.0M--8.00%--Oct-
17--64--38
PASTRANAK--$6.7M--8.89%--Sep-
17--70--26
NYLANDER--$6.9M--8.76%--Dec-18--61--61
Higher cap % then Ehlers and Larkin based on two solid seasons, and a bit less than Pastranak based on him having the breakout 70pt season before his deal.
Seems right in line with his comparables to me.
Not sure how the Leafs taking it to the absolute final min was a sign of weakness (esp. considering he got market value)
Also, it's pretty well common knowledge now that Nylander was holding out for term not $$. His deal was always going to be the hardest, with Matthews and Marner mega deals to follow. Nylander knew/knows he's the most likely to be shipped out, if he didn't fight for term, and ended up taking a bridge, there's no way he's still a Leaf when the bridge is done, as they couldn't possibly afford his 3rd contract with the big 3 signed (incl Tavares) long term.
If anything, the Leafs mistake on the Nylander deal was waiting too long to get serious in negotiations, it was end of summer before they really started, which didn't allow enough time before camp.
Also, letting him sit a season would have poisoned an already fragile room. Babcock would have hated Nylander more than he did already, and likely further alienate the young core. That would have been the wrong move.