Joel Edmundson and Ilya Lyubuskin
While there is no way to predict what the upcoming season has in store, one thing we can say for sure is that the Leafs are highly unlikely to trade for Ilya Lyubushkin at the trade deadline for once. That isn't to say they won't want to, but his new contract is ridiculous and likely makes doing so impossible.
The Dallas Stars signed Lyubushkin in free-agency, giving him over $3 million dollars per season for three years, taking him to age 33. This is a terrible deal because players better than Lyubushkin are always available at the league minimum with no needed commitment.
All I can say about this deal is that at least it will prevent the Leafs from trading for him again. Lyubuskin is a bad player and the Leafs should never have traded for him, let alone twice.
Speaking of dumb Leafs trades, Joel Edmundson also signed a terrible contract this summer. The LA Kings gave Edmundson a four year deal with a $3.8 million cap hit that runs until he is 35. It instantly became one of the worst contracts in the NHL. (all contract info puckpedia.com).
The Kings gave Edmundson a four year deal despite the fact that he's terrible at hockey and already 31. Despite the fact that the Oliver Ekman-Larsson deal is incredibly bad, the Leafs at least didn't re-up with either Lyubushkin or Edmundson, so that is something.