I've always liked Phil Kessel and rooted for him to succeed, but he's been such a wiener this year that I have a hard time wishing him success anymore, to be honest.
He's a good hockey player but I've heard so many accounts of how he slacks off in practice, refuses to stay in shape during the offseason, refuses to lead when he is expected to lead (he may not be a leader in the "rally the troops and will them to win" kind of way but even still, in the corporate world if you accept a job/sign a contract for a job where you're expected to manage or lead people - which was expected of him and made very clear when he came to Toronto - and fail at it through laziness and incompetence, it does not and should not get brushed off as suddenly being irrelevant or "that's just not him, it's no big deal")...it all adds up to a bad taste being left in my mouth. Sure he's a good hockey player and he can score goals but I've played hockey before and those kind of guys can be not worth the hassle of dealing with their constant bullshit.
The final straw for me was when he whined about the media being unfair to him and Dion Phaneuf, and claimed that they're doing their best even though they were in the midst of a huge losing streak and sitting nearly dead last. If I'm fucking up my job on all fronts and get called into my boss's office, and then claim that this shit job I'm doing is actually my best effort, I'm going to be shown the door pretty quickly, and probably be laughed at on my way out. Him saying that felt a bit like a slap in the face, even though I do agree that the Toronto media can be over the top with the stupidity sometimes (that whole "saluting the fans" controversy earlier this year was a crock of made up shit).
Long story short, I've come to realize this year that Kessel certainly won't be the player he has the potential to be in Toronto. Maybe a different coach/system/environment will make it a different story, but he can't stay in Toronto another year and continue to phone it in. I think judging from recent interviews he's checked out too, despite what he says he really seems to be done with the idea of playing hard and doing his best to succeed here. He and Phaneuf both have to go, and the sooner the better for both the players and the team. The question to me really seems to be what kind of return you'll get for him, he definitely didn't help his trade value at all this year.