I think that sometimes we forget that these players who also happen to be multi millionaires are also just regular people. Last night when Kessel was asked about his future he mentioned that he really loves Toronto, but he will go where they want him, I believe someone posted the exact quote earlier. I really felt bad for him, it might just have been my reading of the situation, but I definitely got the sense that he would be hurt to be traded away. I get the sense that since he has essentially matured and grown up throughout his 20s in Toronto, he really does love this city, the lifestyle he is able to lead and loves playing for the leafs. When the team loses I get the sense that he is genuinely pissed off, he could of course be doing more to be an all around more well-rounded player, but I get the sense he is definitely invested and I think you do want to keep guys like that around.
Just my two cents, I could be wrong and most likely am as per the norm, but I hope that Phil sticks around to see and be part of the rebuilt and successful Toronto Maple Leafs.