What a mess of a situation. Kessel is a pouty one-dimensional winger, but it's not like management isn't to blame either.
1) They traded a premium for him when that was absolutely his reputation at the time
2) Management then did NOTHING to try and change that about him. Kessel cheats defensively, doesn't fight for loose pucks, puts in limited effort at practice, etc. Did they ever demote him before? Cut his PP time? Etc? Nope. The management of this team have CREATED the culture of entitlement that exists here, and then they complain about it to the media, talking about accountability/leadership/character without actually doing anything about it.
The Leafs should have taken this hardlined approach with Kessel when he got here. They could have spent a couple of years putting in legitimate effort to mold him into more of a responsible two-way winger, like Kovalchuk became in NJ, or Hossa has become later in his career.
If he didn't respond well to that treatment 4-5 years ago, then we could have simply traded him, and accepted our losses on the whole thing. Instead, worried about upsetting our "star" player, we've wasted 6 years. Not once trying to enforce accountability on him, and now all of a sudden they're trying to do that and are surprised that Kessel is surprised.
Now at 28 years old with 7 years remaining at 8M, he's going to be harder to move than if we'd moved him at 24/25 with a couple years remaining at 5.4M. Our management has had zero vision when it comes to assets, but also when it comes to accountability on the team and how it affects the players.