Proposal: TOR - WIN

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If they’re trading one of Matthews or Marner they need a young #1D in return.

They cannot afford to trade anymore draft picks without getting more picks in return.
 
Over the next two or three years they have to build a D, basically from scratch. They have a great 2 in Rielly and 5 or 6 in Liljegren, but they need a 1,3,4.
 
That's on the right track in terms of attempting to solidify the defense with a big minutes guy plus get a legit starting goalie. I wouldn't do the deal without an extension for Hellebuyck. I'm not so sure that Winnipeg would be all that keen on Liljegren who still hasn't played a lot of playoff minutes which has to be a red flag in terms of his ceiling.
 
If I’m trading Marner (and I would) I want someone who can score with good speed, work ethic and term. Kyle Connor has 4 more years left with an 8.7 cap hit. If you can re-sign Nylander around the same, that’s a good core change.
 
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