Coming from a Leafs fan, Kessel is an elite talent, but his play style lately is the very definition of selfish. He achieves individual success at the cost of team success. I think this is partly due to his linemates though, and the style of play that's been dictated by them. Back when he first joined the Leafs and played on Stajan's line he had a positive +/-, a respectable GA/60, and excellent possession numbers. His game only went to hell when Stajan was traded and Bozak took over. That pair has been more or less a fixture for 5.5 years now, with a series of (bad) coaches refusing to split them up for more than a couple games at a time.
The center on a line does a lot to dictate how the line plays, and Bozak is simply one of the worst possession players I've ever seen, and is incredibly mediocre at defending. He's been pilloried by the analytics community over the past year or two, and deservingly so, he's effectively a 3rd/4th line center who has a bit of offensive flair that makes him look better than he is. He's a much bigger reason for the line's defensive woes than Kessel due to the position he plays.
Anyway, point being ... Kessel is not worth as much as some Leafs fans make him out to be, especially when you consider his contract. Winning these days is as much about maximizing the value from your cap hit as it is about talent. On the other hand, he's not some average player just because he was a minus this year like some non-Leafs fans are making him out to be. He's pretty much an average 1st line RW. Possibly not top 10 in the league, but definitely in that 10-20 range for right wingers.