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Someone in the Leafs front office does not like Phil Kessel. It might be Shanahan. It might be Mark Hunter. It might be Kyle Dubas. It might be Mike Babcock. Perhaps even all four. But either way, the manner in which the Leafs&#8217; most-talented player was just sent out of town really had &#8220;we need to get rid of this guy, and fast&#8221; written all around it, and I&#8217;m not entirely sure why. There&#8217;s a reason though, there just has to be. It all came about so quickly.

Now, without question this trade does fall in line with what the Leafs need to do in burning everything to the ground to try something new, if that&#8217;s what they&#8217;ve committed to. But the urgency here, especially with more pressing concerns on the roster, is surprising, as is the return in the trade. [Though don&#8217;t put me in the camp that believes the Leafs got absolutely killed on this deal. They didn&#8217;t.]
So, why did this happen? And perhaps more importantly, why did it need to happen now? Here, let me try to talk myself into this deal.
There&#8217;s a reasonable argument to be made that Toronto should&#8217;ve simply held on to Kessel if they couldn&#8217;t demand a ransom this summer, and waited until he bounced back this upcoming season, making him a little more valuable next year. I don&#8217;t know if I agree. 
Unless you&#8217;ve been living under a rock these past few weeks, you know the league is experiencing a major shift toward teams targeting and locking up young elite players through their prime &#8211; those 22 to 29 years. Kessel has been an elite talent but he&#8217;s not entering his prime, he&#8217;s leaving it. Even blowing up his boxcar numbers by playing with Crosby (which most expect to happen) won&#8217;t change that.
Strike one on Kessel, he&#8217;s in the early stages of a big contract but in the latter stages of his productive years. This is the case for plenty of players around the league, mind you, but that doesn&#8217;t excuse it. Moving out 8-million AAV now puts you among those suitors for young RFAs and the like (see Calgary with Hamilton, for example) when the time comes to make those sort of moves.
Secondly, does the perception of Kessel with media and fans factor in here? You might hope not, but it&#8217;s difficult to say it doesn&#8217;t. I mean, come on, whether right or wrong, we know it has to.
Just as we all predicted, it didn&#8217;t take long for some of the members of the Toronto media to start sharpening their knives when Kessel was shown the door on Wednesday. He&#8217;s off to Pittsburgh to play with the best puck-distributors in the world (which, after half-a-decade of playing alongside Tyler Bozak, should feel like a hockey fantasy camp), but of course he couldn&#8217;t be seen off without some ugly parting shots from the <a href="http://www.torontosun.com/2015/07/01/leafs-were-sick-and-tired-of-kessel">city&#8217;s most vile</a>. In its worst cases this is no doubt due to some writers and radio folks in Toronto just simply being the worst, but in the bigger picture it&#8217;s because it was probably unfair to both Phil Kessel and the Leafs to ever have him as the go-to guy in such a market.
This might sound like an insane thing to say, but the reason Kessel eventually became such a &#8220;polarizing&#8221; player and found his head on the media chopping block so often is because he was probably too skilled relative to his teammates. Dion Phaneuf, as the captain no less, was supposed to shoulder some of the burden of this team as a core player, but because he saw his play drop and level off so early in his Toronto tenure, he&#8217;s sort of settled in nicely and avoided too much media heat in recent times. People just sort of accepted that Dion is what he is, and it feels like they could never figure out what Kessel was, so they hated him. It also doesn&#8217;t hurt that Phaneuf took a major step forward in his relations with the media since joining the Leafs, and Kessel never bothered.
Joffrey Lupul? Tyler Bozak? Again, nice guys in interviews, so they always get a pass from the media there, but another thing they have going for them is neither has ever really been good enough for anyone to care much if they were in a cold streak. With Kessel it was different, because he just scored, and scored, and scored, and didn&#8217;t seem to care about much else, especially what the trolls, most notably Simmons and Feschuck, thought of him. It drove them insane. 
But still, there&#8217;s more to it, because even the most reasonable reporters seemed to never really fall in love with Kessel.
<blockquote>Kessel was not the type to lead a team, though he was put in the position to do so, optically. Ownership and management and coaching put Kessel in a spotlight inappropriate for him and fans rightfully balked. It&#8217;s neither their fault nor his. There&#8217;s no fault to be passed around here. Sports fandom is for playing favourites while irrationally hating exemplary human beings like Daniel Alfredsson.</blockquote>
<a href="https://sports.vice.com/en_us/article/phil-kessel-was-never-loved-in-toronto">Those are some lines from an article by Joe Pack at VICE</a>, and I think they sum up the Kessel era quite nicely. Pack is right, there is no fault to be passed around here. Well, there is, but anyone you&#8217;d pass it to is long gone, thankfully. For Kessel, Shanahan, Dubas, whoever was left, they&#8217;re all just trying to move on in whatever directions seem best after the debacle that was Nonis in Toronto.
It&#8217;s difficult to filter out the truth from childish ax-grinding when you have people like Steve Simmons floating around, but we can probably try to make some conclusions about Kessel without making this about lowbrow fat jokes or some other junk. There is a middle-ground here. 
To me, as an outsider, it really seems as though Kessel&#8217;s sort of laid-back attitude stretched beyond his relationship with the media, and the Leafs&#8217; front office felt he couldn&#8217;t be relied upon to build around with new kids like Marner and Nylander entering the fold soon. It absolutely pains me to say it, but I think they wanted a better example for this next group &#8211; not even so much in terms of performance, because Kessel was always elite on the ice, but just in how to be the face of a franchise.
And<a href="https://twitter.com/ShawnMcKenzieSN/status/614844409822228480"> this quote from Mike Babcock from the draft </a>probably gives us even more insight into what kind of conversations were happening behind closed doors.
<blockquote>We are going to be a fit, fit team. We are going to be a team that goes to the media every day after a win or a loss or practice and owns their stuff. Period. When it&#8217;s good, it&#8217;s good, and when it&#8217;s not you&#8217;re going to step up.</blockquote>
I have no problem with the way Kessel handled himself in Toronto (then again, I probably don&#8217;t know the entire story), but I&#8217;m guessing Shanahan felt it wasn&#8217;t the right way for a key piece to operate, and didn&#8217;t want it to be the norm for up-and-comers. Maybe this new philosophy Babcock wants to unroll is something Kessel could have dealt with, or maybe not. But what the trade says is Shanahan didn&#8217;t know if Kessel could &#8220;step up&#8221;, and he obviously didn&#8217;t feel like he could wait to find out.

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</div></center>Someone in the Leafs front office does not like Phil Kessel. It might be Shanahan. It might be Mark Hunter. It might be Kyle Dubas. It might be Mike Babcock. Perhaps even all four. But either way, the manner in which the Leafs' most-talented player was just sent out of town really had "we need to get rid of this guy, and fast" written all around it, and I'm not entirely sure why. There's a reason though, there just has to be. It all came about so quickly.Now, without question this trade does fall in line with what the Leafs need to do in burning everything to the ground to try something new, if that's what they've committed to. But the urgency here, especially with more pressing concerns on the roster, is surprising, as is the return in the trade. [Though don't put me in the camp that believes the Leafs got absolutely killed on this deal. They didn't.]So, why did this happen? And perhaps more importantly, why did it need to happen now? Here, let me try to talk myself into this deal.There's a reasonable argument to be made that Toronto should've simply held on to Kessel if they couldn't demand a ransom this summer, and waited until he bounced back this upcoming season, making him a little more valuable next year. I don't know if I agree. Unless you've been living under a rock these past few weeks, you know the league is experiencing a major shift toward teams targeting and locking up young elite players through their prime - those 22 to 29 years. Kessel has been an elite talent but he's not entering his prime, he's leaving it. Even blowing up his boxcar numbers by playing with Crosby (which most expect to happen) won't change that.Strike one on Kessel, he's in the early stages of a big contract but in the latter stages of his productive years. This is the case for plenty of players around the league, mind you, but that doesn't excuse it. Moving out 8-million AAV now puts you among those suitors for young RFAs and the like (see Calgary with Hamilton, for example) when the time comes to make those sort of moves.Secondly, does the perception of Kessel with media and fans factor in here? You might hope not, but it's difficult to say it doesn't. I mean, come on, whether right or wrong, we know it has to.Just as we all predicted, it didn't take long for some of the members of the Toronto media to start sharpening their knives when Kessel was shown the door on Wednesday. He's off to Pittsburgh to play with the best puck-distributors in the world (which, after half-a-decade of playing alongside Tyler Bozak, should feel like a hockey fantasy camp), but of course he couldn't be seen off without some ugly parting shots from the <a href="http://www.torontosun.com/2015/07/01/leafs-were-sick-and-tired-of-kessel">city's most vile</a>. In its worst cases this is no doubt due to some writers and radio folks in Toronto just simply being the worst, but in the bigger picture it's because it was probably unfair to both Phil Kessel and the Leafs to ever have him as the go-to guy in such a market.This might sound like an insane thing to say, but the reason Kessel eventually became such a "polarizing" player and found his head on the media chopping block so often is because he was probably too skilled relative to his teammates. Dion Phaneuf, as the captain no less, was supposed to shoulder some of the burden of this team as a core player, but because he saw his play drop and level off so early in his Toronto tenure, he's sort of settled in nicely and avoided too much media heat in recent times. People just sort of accepted that Dion is what he is, and it feels like they could never figure out what Kessel was, so they hated him. It also doesn't hurt that Phaneuf took a major step forward in his relations with the media since joining the Leafs, and Kessel never bothered.Joffrey Lupul? Tyler Bozak? Again, nice guys in interviews, so they always get a pass from the media there, but another thing they have going for them is neither has ever really been good enough for anyone to care much if they were in a cold streak. With Kessel it was different, because he just scored, and scored, and scored, and didn't seem to care about much else, especially what the trolls, most notably Simmons and Feschuck, thought of him. It drove them insane. But still, there's more to it, because even the most reasonable reporters seemed to never really fall in love with Kessel.<blockquote>Kessel was not the type to lead a team, though he was put in the position to do so, optically. Ownership and management and coaching put Kessel in a spotlight inappropriate for him and fans rightfully balked. It's neither their fault nor his. There's no fault to be passed around here. Sports fandom is for playing favourites while irrationally hating exemplary human beings like Daniel Alfredsson.</blockquote><a href="https://sports.vice.com/en_us/article/phil-kessel-was-never-loved-in-toronto">Those are some lines from an article by Joe Pack at VICE</a>, and I think they sum up the Kessel era quite nicely. Pack is right, there is no fault to be passed around here. Well, there is, but anyone you'd pass it to is long gone, thankfully. For Kessel, Shanahan, Dubas, whoever was left, they're all just trying to move on in whatever directions seem best after the debacle that was Nonis in Toronto.It's difficult to filter out the truth from childish ax-grinding when you have people like Steve Simmons floating around, but we can probably try to make some conclusions about Kessel without making this about lowbrow fat jokes or some other junk. There is a middle-ground here. To me, as an outsider, it really seems as though Kessel's sort of laid-back attitude stretched beyond his relationship with the media, and the Leafs' front office felt he couldn't be relied upon to build around with new kids like Marner and Nylander entering the fold soon. It absolutely pains me to say it, but I think they wanted a better example for this next group - not even so much in terms of performance, because Kessel was always elite on the ice, but just in how to be the face of a franchise.And<a href="https://twitter.com/ShawnMcKenzieSN/status/614844409822228480"> this quote from Mike Babcock from the draft </a>probably gives us even more insight into what kind of conversations were happening behind closed doors.<blockquote>We are going to be a fit, fit team. We are going to be a team that goes to the media every day after a win or a loss or practice and owns their stuff. Period. When it's good, it's good, and when it's not you're going to step up.</blockquote>I have no problem with the way Kessel handled himself in Toronto (then again, I probably don't know the entire story), but I'm guessing Shanahan felt it wasn't the right way for a key piece to operate, and didn't want it to be the norm for up-and-comers. Maybe this new philosophy Babcock wants to unroll is something Kessel could have dealt with, or maybe not. But what the trade says is Shanahan didn't know if Kessel could "step up", and he obviously didn't feel like he could wait to find out.

Maybe Kessel had to be traded for his own sake

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