Ok, without even debating the PK/Weber trade (which i still say his a loss cause of age). here are some losses.
- The 2017 trade deadline... Andrighetto for Martinsen, Draft picks for Ott and Dwight King. (Didn't address team needs, gave away assets for players who didn't add to the team's offense), minor loss
- Andrew Shaw for 2 second rounders (Alex DeBrincat and Chad Krys). I like Shaw but he overpaid.
- Acquired Stefan Matteau, traded Devante Smith-Pelley (small loss, but a loss)
- acquired Parenteau and a fifth for Briere (Briere had 1 year left on his deal, Parenteau had 2, we ended up buying out Parenteau's second year).
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Overall he wins more than he loses, but no one is perfect and those are losses IMO.