He had some leverage with Matthews in the sense that the deal didn't need to be signed immediately. At the very least he should have tried very hard to get another year or so.
The Nylander deal was horrid simply because at that point let him sit. Sign Marner, make sure you have as balanced a team as possible going into the new season, and then tell Nylander this is what is left for you and if you don't like it be prepared to sit forever.
But instead he basically went and threw away all the leverage he had and got nothing in return. Just terrible.
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