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The new CBA (if we ever get one) and the Phil Kessel conundrum

You may have zero interest in discussing the CBA, the lockout and all that stuff, but just in case, feel free to visit this story, which asks you if you would follow the old NHL, or a new league- if the current players bolted and formed their own place to play!


I’m trying to think back, but for all the discussion we’ve had here over the past three years about Phil Kessel (and the deal that brought him here from the Bruins), I don’t believe I’ve ever suggested it was a bad deal for the Leafs—or that I believe the Leafs should try to trade Kessel for something even “better”.  I like Kessel a lot.  He's an entertaining player and the Leafs have lacked a big-time threat (not to mention legitimate excitement around here) for a while.

Of course, we have often batted around the pros and cons of the deal that ultimately saw Tyler Seguin and Doug Hamilton land with the Bruins after being selected in the first round in their respective drafts.  It's only natural for us, as fans, to assess the relative merits of any trade, but especially one with implications like the Kessel move.  Part of the enjoyment of being a fan is that we get to play “Monday morning quarterback”.  And, as erstwhile arm-chair GM’s (and critics), we get to opine of the wisdom of such deals—usually after the fact.

There is no doubt that Kessel has brought exactly what Brian Burke though he was getting when he made the bold move to acquire the oh-so-young and ultra-talented winger—just as he was ready to emerge as a legitimate top-line player at the NHL level.  In the same breath, the Bruins have certainly derived satisfaction from the deal as well.  For whatever reasons, Kessel and Boston coach Claude Julien did not quite mesh, and the Beantowners have since won a Cup with Seguin playing a rather limited- though still useful- cameo role in the spring of 2011.  The young center made major strides this past season, and just signed a new long-term deal with the Bruins.

We may be able to make the statement that both teams did well by the trade, and perhaps even defend that claim.  But as Leaf supporters, we can’t quite get around the fact that, if the Leafs ever win a Cup with Kessel, they’ll still only be catching up to what the Bruins have achieved since they drafted Seguin- with "our" pick.

What roster would you rather have right now?  And honestly, who would you rather have in tow—Seguin in the middle and Hamilton on the Leaf blueline, or the guy we already have, with a series of 30-goal seasons behind him- and maybe more to come?

Here’s the rub, however.  Kessel has been, if sometimes inconsistent, a major impact player for the Leafs.  As much as the team has struggled in his three years in blue and white, can we imagine what we would have been without him in the line-up?

Unfortunately, we have not been able to take advantage of Phil’s speed and youthful zest (when he shows it), having not yet provided him with the opportunity to play in even a single playoff game in his time here in the big smoke. That can change very quickly of course, but this all leads me to a question that some Leaf fans don’t even want to ponder—much less discuss or consider.  And that is this:  if we (and more importantly, Burke) step back and look at this roster and see that a) the Leafs just are not, realistically, playoff (much less Cup) contenders this season (if there eventually is one) and b) Kessel may fly the coop in free agency a couple of years down the road, then what is the best thing to do about Kessel?

I posted recently about Kessel in the broader context of whether he is in the “he is what he is” category of player.  Meaning, that he’s a really nice offensive winger who can make plays and score goals, but will he ever be more than that?  Does he need to be more than what he is now?  Will he ever be a playoff performer in the tough going?  A leader?

But beyond even that, can we surround him with the kind of talent that will actually fully exploit Kessel’s skills and help him take the Leafs far into the playoffs in the foreseeable future?

I think those are legitimate questions, and those may be the very questions that Burke and the brass will be thinking deep thoughts about in the months ahead.  (They'll have plenty of time during the lockout...)  Do they re-sign Kessel by next summer to one of those new, long-term (six years? Ten  years?) deals and pay him, say,  9 million or more a season? Or....

Sure, it will depend on the new CBA and the cap and all that, but the stars will still get their money (they always do), whatever the cap implications.  Teams need their big guns to compete.

If that’s what the Leafs decide they want—that is, to pursue and sign Kessel to a mega-deal - will that be the right move for a player some see as limited because of the above question marks? Is he worth the kind of huge dollars that others are now getting?  What would he command as a free-agent?  Is he seen in other markets as an Alexander Semin, in terms of temperament?  Or is he more of a Rick Nash, or something in between?

At the end of the day, the Leafs (and Kessel) will have to decide what they really want.  If Kessel wants out, the decision is easy—trade him for as much as you can get, as soon as you can get it.

However, if Kessel plays coy, and the Leafs don’t really know his intentions (I know we’re talking Leafs, not the NBA Raptors who have seen that movie all too often, but there is still a risk...), could they miss out if they hold on to him and he then signs somewhere else? What if he leaves in free-agency and we’ve never hosted a playoff game in all the years that Kessel has been here?  Meanwhile, the Bruins will have at least one cornerstone player (maybe two, depending on Hamilton's actual development) for years to come.

Bottom line, how do you see the young Leaf winger?  What would you do in Burke’s shoes?  Is he worth a big deal to the Leafs?  Is it better that he be used in a trade at some point to help management build an even better team, with more grit and veteran moxie in the years ahead?

And when do these decisions have to be made?

Again, I think these are not only fair and reasonable questions, I believe these discussions are happening as we speak, or soon will, as soon as the  new CBA is settled.

I’d be interested in how you see this shaping up…..


  1. While I have actually heard rumblings of these concerns elsewhere and do appreciate the broad range of your queries, you may be a little ahead of the curve, here! I actually feel that all decisions about Kessel will depend upon the outcome (or actual presence) of this current season.

    If we don't play at all, then we have no real idea where we will stand with player development and upcoming prospects. We must also be mindful that we will see the expiry of a number of contracts at the end of the year and upcoming free agent signings may have some clear impact on the decisions pertaining to (and for) Kessel.

    If we play, a foray into the post-season may tell us what kind of player we have in a 7th season Kessel. I believe that performance opportunity might have a lot to do with his future with the club. I hope he has the opportunity to thrive (if this season actually begins) and that there will be some means to keep him in the fold as a valuable asset to a team that has become deeper by the time a decision must be made.

    I'd hate to lose him without seeing him a little longer!

  2. InTimeFor62- Thanks. I recognize that I'm discussing this particular subject a bit early, but I wanted to talk hockey, rather than the lockout today!

  3. Kinda realized that after I posted! Thanks for giving us something else to think about!

    I believe Burke still feels Kessel fills a role, but since the latter can't be all things to all people, we often find fans trying to trade Kessel to 'get what we need.' I don't think that is in BB's cards. I expect Kessel to be here for quite a while!

  4. Michael,

    The Kessel trade. The cause of, and solution to all of the Leafs problems. I would like to mention that if the Leafs don't trade for Kessel how much worse they would have been for those seasons. It may have been back to back number 1 picks. He is a dynamic player, and no one else on the team was capable of putting the puck in the net at that rate. They would clearly have been worse. I think a lot worse off without him.

    Call this a hunch or a gut instinct, whatever you like. I feel like Phil Kessel is always going to feel uncomfortable being a star in the NHL. Unwilling to stand in the spotlight, with all the focus and attention. He seems to like the media about as much as I like lawyers. I do not see him re-signing to play here once his contract is up. I also don't feel that he will have any problem getting another team to pay him huge money. I also wouldn't be surprised to see him sign a contract in Toronto and then quietly ask to be traded. Burke would do this if Kessel went about it the right way. Media silence, or no trade. It would kill Burkes' legacy, if he has one. But he does seem to be honourable, so I think he does it.

    I see Kessel as a better version of Alex Semin. A softer one way player who has an immense skill set. Yet, someone uninterested in the more menial aspects of the game. He is certainly an entertaining player, not sure that he is what you build a championship team around. Keep in mind that Semin ended up getting seven million this offseason. Not bad for a guy who is perceived as a soft, one way guy.

    When all is said and done. It seems to me that Burke put all his money on the wrong horse. He is young, dynamic and supremely talented. Too bad that it is in a supporting, not a starring role.

  5. I think you've captured what I'm talking about very well, Jim. He is a very talented young player. But to a certain extent his time here has been wasted (and as a result, what we ended up giving up seems even more magnified...) because we simply have not surrounded him with what the team needs to be truly competitive.

    I'm clearly no GM, but there had to be a follow-up to the Kessel trade. I suppose Phaneuf was intended to be that big piece on defense, but that has not yet worked out as planned/hoped for from management's perspective. They would never admit that, of course, but I think it's true.

    So many issues to deal with. Should Kessel be a supporting guy, as you suggest, rather than a lead guy? Is there enough time to develop the supposed prospects while hoping Kessel stays? If he stays, does he put you over the top, or struggle at crunch time?

  6. I agree in large part with Jim.

    I think you bracketed Kessel very well as being somewhere in between Semin and Nash; probably a lot more like the former than the latter and so someone who needs another big piece alongside him. Like Jim, I think where we've missed the boat is by not following up his trade with another to complement him and I have my doubts that JvR will have the watts. Here's hoping I'm wrong or that Joe Thornton suddenly and miraculously gets homesick.

    I'm not sure that this season will make much difference to BB's plans though. Now that it's a given that it will be short at best, Burke has all the excuses he needs to ignore whatever happens if it doesn't suit his preferred message. I'd like to see Kessel stay, on balance, but I don't expect him to want to unless he and Lupul have another PPG bromance season.

  7. Kessel wanting to stay is part of the equation, for sure, KiwiLeaf. (Of course, the Leaf brass has to determine his value and how much they want him here, as opposed to as a trading piece...) He remains one of the intriguing debating points as we move toward a new season- or not. Thanks for chiming in.

  8. Hi Michael,

    I can't agree that the Leafs would have been worse off without Kessel. 26th overall or 29th overall makes little difference.

    We would have had Seguin, assuming that the Leafs didn't drop the ball on that pick, who happens to be a 30 goal scorer after two seasons. He also plays a hard nose brand of hockey that we lack around here. We would also likely move a couple of places up the draft order and get some decent players as a result.

    I am also concerned that, since that ship has sailed, we have not taken steps to lock up Kessel long term. If nothing else, Burke should have noticed that all of his peers have taken that step with their important players. So, either Burke is the smartest guy in the room or he has been negligent. One thing that we know is that there will be few if any free agents available to replace Kessel. And, we have a somewhat poor record signing free agents.


  9. Michael
    One thought that popped to mind as I read your post today was why didn't the Leafs sign Kessel to a big contract extension just before the CBA deadline? Was it that Kessel wasn't interested? Or we're the Leafs not interested or inclined to do that?
    Other clubs locked up their key players with extensions thus limiting the supply of free agents in the near future if the Leafs were planning to build the team that way.
    Personally I hope we keep him as pure scorers don't grow on trees. I like him but I agree he needs to be surrounded with more talent such that he is not the "number 1" guy in the spotlight. I think he would be able to quietly flourish if he wasn't in that media and fan spotlight.
    If Burke was planning to keep him, wouldn't a contract extension have been useful to avoid losing him to free agency?
    Just wondering.

  10. I can't argue that we could not have been much worse even without Kessel, Brad (cbh747). One you miss the playoffs, where you end up in the standings makes precious little difference, agreed. Sadly, we have not made even one round in his time here.

    The Bruins just locked up Seguin. I would think, if Burke believes Kessel is still a vital cog, he will do the same with Phil once a new CBA is finalized.

    Thanks Brad.

  11. You raise a good question Ed, and while we all understand there is a lockout in place, teams were signing key players, as you mentioned, right up to the expiration of the old CBA. And there is still a business to run, even now, so I'm sure the Leaf brass is having these very discussions. Well said, thanks Ed.

  12. At the risk of beating a dead horse on the enigma that is Phil Kessel, I'll add a couple thoughts on the trade, his reputation coming in, and his performance once in Toronto.

    I always defended Kessel, and felt he got a bit of a bum rap. For all the stories I heard about him being lazy, uninspired, a locker room cancer even. Yes, the "C" word. Does anyone remember his battle with cancer, the real kind that can kill you? Here was a kid of 19, thrust into the NHL spotlight, and battling cancer. He was quiet throughout that, received his treatment, and re-joined the Bruins as soon as he was able.

    I think people tend to forget the ramifications of sending 18 and 19 year olds into the professional ranks, and the growing pains involved. Yet somehow the tag stuck on Kessel far too early in his career that he is a bad teammate. He was never given the benefit of the doubt and the opportunity to grow up.

    Your column some time back asked generally if we should just accept him for what he is. I say yes, we know what we have in Kessel. A flashy, one-way player who will never be confused for team captain. Is he a liability? No way!

    As for his future, I think his next season affords the Leafs the luxury of watching and seeing what happens with him. Is he going to explode with 50 goals depending on who his linemates are? Or will he regress? That will go a long way in determining his market value for the future. Then it becomes time to negotiate with him on an extension. If Kessel rejects any notion of a five-year contract at a reasonable rate, it's time to trade him before the contract expires. I say this because, being the type of player he is, he is at his peak performance time. A pure goal scorer like Kessel will not continue at that pace well into his 30s if history is any indication. Most players have to learn to play a better two-way game to survive that long in the NHL, and I don't believe that will ever be the case with Kessel. I shudder to think of locking Kessel up until he's 35 years old, and dealing with what's left of him at that point.

  13. I think that's a fair but also very practical assessment of Kessel's situation, Pete, as we try to determine his "value" in the years to come.

    I guess the discussion, as Ed and Brad alluded to in part, also has to do with locking him up early (which the Leafs have not done yet) versus waiting things out. It would be hard to imagine the Leafs letting Kessel slide into free-agency without a contract- or trading him.

    But you make a very good point that his next season should be telling, and may indicate what the Leafs (and he) want to do. Thanks Pete.

  14. I'm a Kessel supporter. What more do we want from him? Gifted scorer, dangerous playmaker, game changer... that's enough for me. He's been with Lupul for less than one season, and their chemistry can't be denied. Even Bozak has improved playing with them. No, he's not Yzerman - but who is? Let's improve the supporting cast and see what happens.
    As for "the trade" - do we really think Seguin would have blossomed on this Leaf team? I don't. We'd probably still be shuffling him back and forth to the Marlies. He's done well with the Bruins because of his limited role and the quality of the rest of the team.
    Lock Kessel up? I don't think we've seen enough to do that - and we don't know if he even wants to stay, as you point out. GM's generally like to keep their options open, and I get the feeling the current situation works for both sides.

  15. Your last sentence is the kicker, Gerund O' of this moment, the status quo seems to be working. At some point, one or the other will likely want to make this a more permanent arrangement. Thanks Gerund O'.

  16. Players involved in a blockbuster trade are inexorably linked in the minds of fans and pundits. This is inherently unfair to the players involved. They should be judged on their piece of work alone and not in terms of what the person they were traded for has done.
    Those judgements fall into the realm of the general manager.

    Critics have too often dwelt on what Phil Kessel isn't and not what he is. In this he reminds me of Frank Mahovlich. Mahovlich was an exciting offensive force who could bring a crowd to its feet but was criticized for his alleged lack of desire. Kessel is also a prolific offensive player who is dynamic and exciting but has been criticized for his defensive deficiencies and lack of charisma.

    If we look at the positives, Kessel has been everything that was expected (hoped for) when the trade was completed for undetermined draft choices. What those draft choices morphed into should be irrelevant when evaluating him.

    Kessel can be a very important piece of improving Leaf future teams. I really hope they resign him in 2114.

  17. The Mahovlich reference is apt, Pete Cam. Back then, we always seemed to want "more" from the Big M. (We both remember that Frank ultimately went on to be a vital cog in Montreal winning Cups in 1971 and 1973.)

    Kessel may not become that kind of impact guy, but you make a good point- that how we assess him should not be influenced by what he ended up being traded for...

  18. MIchael,

    Any thoughts today on Allaire leaving the Leafs position as goalie coach? Suggesting that they don't need one and that they have too many as it was.

  19. Post upcoming later tonight. Thanks Jim.

  20. I'm no expert on these things, but I think that an extension for Kessel can't be negotiated until he's into the last year of his current contract. This may be the reason that no extension is forthcoming. Perhaps someone else knows for sure...