I still don't think it's a good deal for Toronto. Not if they are going to wait so long. They're going to have like $40 million wrapped up in four players, and potentially a Nylander who is less than happy.
Either way, as soon as Marner and Matthews get signed, they are going to start hurting for depth. If they don't win in the next two years, they may actually get much worse over time. This is like Chicago all over again, except it's after Chicago won their Cups, and was forced to shell out the cash.
That's the risk here. Chicago was able to shell out the cash after they won a bunch. Once they did so, they stopped being the elite team they were, because they had no depth to support their talent.