The draft was the perfect time for a trade
The Lily contract is probably the most short-sighted move we've seen by this current front office yet. 100% avoidable and a missed opportunity to spend that money better in free agency
Have to agree on this one..
You don't trade a somewhat-stalled mid-20s project in August or at the beginning of the season. It's far too difficult to find a "hockey trade" because teams can't build their offseasons around that trade.
The time to move Liljegren is at the draft, so that the Leafs can go in knowing what they need to spend on the blueline, and another team can go into offseason knowing they have Lily.
That being said, my personal suspicion as to what happened -- the Leafs had a deal lined up for Liljegren, and figured to make it more palatable they'd eat a chunk of bonus money. Their intent was to sign both Chris Tanev AND Matt Roy.
Roy went to Washington, which left the Leafs with Liljegren + $3.5m of cap space that they figured to spend on OEL, and then with Hakanpaa's injury status, they figured "what's the point in moving him now??".