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Can the Leafs afford a lame-duck Kessel this coming season?

When I wrote about Cody Franson’s contract status the other day—and if and where he would fit with the Maple Leafs going forward—I realized as I was developing that piece that I was not addressing the real elephant in the room: do the Leafs need to sign winger Phil Kessel to a long-term contract before a new season gets underway? (On the Franson matter, we'll see if Fraser's new deal will make it easier for Nonis to re-sign Franson...) 

Both sides are saying little, of course.  It’s not Kessel’s “style” to make public waves out of the blue and Nonis is hardly about to start talking about any negotiations that are—or aren’t—happening in public.  But there are two things that I keep batting around in my own head, and I really believe they are relevant to any discussion about the kind of team the Leafs will be in the years ahead:  is Kessel the kind of player that you want to pay superstar/cornerstone player money to and if so, does that type of deal not have to happen now, before he smells free agency and his agent nudges him to seek the largest and longest-term deal he can? (Keep in mind this will be Kessel’s one and only opportunity to hit pay-dirt in free-agency when he is still 20-something.  He will sign for at least six seasons and by then, players with his attributes, in my view, tend to decline. This is his ultimate earning window.)

I know some people (and teams) are of the view that these things can always get worked out later, as in why not put off until tomorrow what doesn’t really have to get done today.  But the problem I see with that is very simple:  I’m sure the Predators thought Gary Suter was happy in a low-stress environment and that they could convince him to stay a Predator for life.  That didn’t exactly happen.

It was the same with Parise and the Devils.  I believe Lou Lamoriello honestly thought he would be able to get the gritty winger to re-sign for at least a bit of a hometown discount, given his relationship with the organization and his growing popularity with the fans in Jersey.

Again, we know how that story ended up.

Both of those guys were hard-working, high-end, loyal individuals.  Yet they did not sign with their respective teams before free-agency was upon them, and then bolted the moment they had the chance—though they were both offered huge money to stay.

I’m sure we have all noticed the trend in recent years, NHL teams trying to lock-up their best and most productive players before they hit their free-agent season.  There is no doubt they sometimes over-pay, but as Anaheim did with Getzlaf and Perry, they want to make sure they don’t lose the core of their team for nothing if those players were to walk in free-agency.

I know that Leaf fans (some, at least) will feel that with Bozak signing his new deal, his friend Kessel will naturally want to stay here and play with his buddy for the rest of their NHL lives. That said, I see little evidence over the years of “friendship” leading to players staying with their current clubs.

But before we get to the second of my questions, let’s  talk about the first:  is Phil Kessel the kind of player, in your opinion, that the Maple Leafs should be investing “best player”/cornerstone money to?  We all know that, in this day and age of monopoly money, that means a minimum of 8 million dollars a season for what, seven or eight seasons?

Now, that type of money usually goes to guys who are not just highly-skilled but also leader types, individuals who are multi-dimensional players.  (Not always, I realize—Kovalchuk, for example, was never thought to be a true leader and certainly not a complete player until more recently…)  I want to be careful how I frame this, but Kessel, while still young and maturing, has never presented as anything close to a leader with the Leafs. His teammates may beg to differ, but I just don’t see it.  A dynamic player, sure.  Explosive and  dangerous, yes.  Maybe even a game-changer in the current-era tight-checking NHL, because he can score out of nowhere and turn the tide in a game suddenly.  That has value, absolutely.

We know he will likely never be Bryan Trottier, Bob Gainey or a latter-day Steve Yzerman as a defensive forward (or Pavel Datsyuk, for that matter) but we also have seen a gradual (if at times almost imperceptible) development in his two-way game under Carlyle.

He’s in or just entering his prime.  So is he the kind of performer that deserves (or even if he doesn’t deserve it, are the Leafs in a place where they need to lock him up because he’s the best they’ve got?) cornerstone player money for almost the next decade?

And depending on how you feel about that may directly impact how you respond to our second question today:  do the Leafs need to act now, this summer, to extend Kessel to ensure we don’t go into a lame-duck season?

We all know what often happens in these cases.  If no deal is reached, training camp begins and if nothing happens by the beginning of the regular-season, both parties will agree to put off negotiations until after the season so it won’t be a “distraction” for the player or the team. 

And we know, in today’s NHL, how that movie usually ends.

Maybe you don’t particularly care if Kessel stays.  Perhaps you’re in the (small?) contingent of Leaf supporters who actually feel we should “sell high” and get a boat-load of younger players and prospects for Kessel or maybe even that stud defenseman I/we keep talking about here.

Whether or not they see him as a superstar the Leafs can build a championmship team around (we're back to that leadership thing again), my sense is most Leaf fans would in fact like to keep Kessel as a central piece for the future.  Still, for that to happen, I have this feeling that Nonis needs to make something happen—and soon.

Your thoughts?


  1. If you had asked this question a year ago I would have quickly answered that the Leafs should trade him. I suspect it was half due to the maddeningly uninvolved way Kessel sometimes plays, and half due to the fact he reminded me of Burke and what might have been with Seguin, and Hamilton.
    But to my surprise, my opinion has mellowed since the playoffs. I think it happened when he seemed to throw off some of the baggage he carried every game against the Bruins. I am even sure I recall him throwing a bodycheck against a Bruin (even if it wasn’t much of a check, at least he made the effort). Finally I felt I a reason to be a supporter.
    But I am concerned that Phil will drift back to being that too-often uninvolved, peripheral winger. And I wonder how committed he will be to do the work needed to stay productive after 4-5 years, as he gets older.
    So with that in the back of my mind, even the mellower me says trade him. In my view they should sign him to a new contract for the high end dollars being mentioned. But either signed long term or not, come next spring if the Leafs are not in a playoff position I hope they look to move him for one or two top calibre young players or lottery draft picks. On the other hand, if they have locked up a playoff spot then keep him for the run.
    Michael, thanks for your interesting columns. So far as I’m concerned, you have the best Leafs discussion out there.

  2. My sense is quite a number of Leaf followers have seen their perception around Kessel evolve over the last season or so. His performance against the Bruins in the playoffs no doubt convinced many fans who had always liked him and his skill level- but found his occasional lack of passion (and production against the Bruins) troubling. After he delivered at crunch time against his old team and former nemesis, the sentiment has shifted more toward his being a legitimate impact player.

    It's interesting that you still are of the view that the Leafs should consider moving him. I wonder if others feel similarly?

    I agree that down the road, he strikes me as a player who may fall off quickly. Any loss of speed/desire won't be easily offset. He's not yet (will he ever be?) the kind of winger who will outwork the opposition and thus be able to make up for any decline in elite skill.

    Now, that may be, as you say, four or five years off. In the meantime, do the Leafs need him as a foundation piece to become a championship team? Based on what you are saying, you may be of the view that they are still two or three years away, and if so, he may be worth trading him for "futures" who will emerge just as the Leafs are really good.

    Thanks for kick-starting the discussion, Steve. And thank you as well for the kind words about VLM.

  3. Give him what he wants. It's not every day you have a 40 goal scorer (potential 50 goal scorer) already wearing your uniform.

    I apologize because I'm sure you were looking for a more nuanced argument, but I think sometimes it just is what it is.

  4. Hi Michael

    Me and a couple of my friends here in New Zealand who are NHL fans run a kind of pool here every year where we draft ourselves teams and accumulate points. You know the kind of thing.

    When we are getting an idea of how to sort the players for drafting, we multiply the amount of points they scored in a season by the points per game for that season to produce an index. Then we weight those indices from the last 3 years so that last season is more important then the year before that than the year before that. When you do that calculation, the only players more valuable to their teams (in terms of scoring points) over the last 3 years than Phil Kessel are (in order) Crosby, Stamkos, St. Louis, Giroux, Ovechkin, Kane, Malkin.

    So, yes, I'd pay the man.

    You just don't willingly let players on that sort of list go, you build around them and their inherent strengths. You fire coaches instead of trading these guys unless they are utterly toxic in the dressing room. And while Phil appears to be a fragile wee soul with his quirks, you'd hardly describe him as toxic.

    1. Thanks for that, KiwiLeaf. I guess one of the questions would be: what would a team have to pay to acquire (as a free-agent) a player like Kessel? And what would assets would you have to give up to obtain someone with his skill set and offensive numbers?

  5. We have witnessed the gradual transformation of Phil Kessel from a pure sniper to a well rounded unselfish offensive player who is equally adept at scoring goals and setting up teammates with pinpoint passes. The defensive part of his game has come along more slowly but I detected a marked improvement under Carlyle. He has become more responsible in his own end and has even developed a little edge to his game. Many elite offensive players gradually develop a defensive game and morph into complete players. I believe that Kessel is on that path.

    The Leafs have plenty of outgoing forwards who can fill the leadership roll. Definitely Lupul and Kadri and I suspect Clarkson and Bolland. Kessel can quietly lead by example.

    I liken Kessel's situation to that of another great Leaf of the past. Frank Mahovlich came to the Leafs with great fanfare. He was, like Kessel, an accomplished sniper and developed the rest of his game over a period of time. Mahovlich also led by example. He was not outgoing and you rarely heard quotes from him in the papers. He never, to my recollection, wore a C or A on his Leaf sweater (I believe Pulford, Stanley and Horton wore A's and of course Armstrong wore the C; and yes we called them sweaters back in the day, not jerseys) but more often than not he was the straw that stirred the drink.

    I rued the day when Mahovlich was traded. He was a unique talent that only comes along rarely. I believe that Phil Kessel is such a talent and that it would be a huge mistake to trade him. I believe that the Leafs must sign Kessel to a long term contract; the sooner the better.

    I can't think of a more reticent GM-player combination in the NHL. Thus I would not expect to hear any posturing from either of them. I just hope that Nonis will quietly strive to sign his young star.

    1. Like you, Pete Cam, I well remember "The Big M". It's a shame, really, that some of the best hockey he played came later in life when he got away from Imlach and the pressures of Toronto, including his time with Detroit, and of course Montreal where he was hugely instrumental in them winning Cups in '71 and '73.

      If, as you say, Kessel can follow a career arc similar to, say, Yzerman and Modano, and become more of a complete player, he would indeed be special. Even if he doesn't, he brings rare skills, for sure.

      It's hard to know what Kessel is feeling and thinking, but I sense Nonis will do everything he can to sign him. Thanks Pete.

  6. My opinion about Phil Kessel has radically changed over time. Initially, I was concerned that the price was too high. When I first saw him play I felt that he was far too one-dimensional. When the actual cost of the trade became apparent, I came to rue the day that Burke made the trade. As everyone agrees however, he has transformed into a more complete player. Without doubt, my position has changed from hating the trade to feeling ambivalent about it, and even more of two minds as his game continues to evolve. If he continues to improve the way he has, I could end up liking it. I cannot remember my opinion about a trade changing so much over time.

    As far as trade him or sign him goes, I am in the camp articulated by Steve Colombo. I would listen politely to offers. (I am assuming there is no NTC in the mix and Nonis can do as he pleases.) That said, any offer would have to knock my socks off for it to make more sense than an extension. On the other hand, if the Kessel vibes are that he wants to go down the free agency path then I would be listening intently to offers. Better to strike when the iron is hot than to be left high and dry next July.

    1. Kessel is a player that can confound and confuse, Bobby C., so it is not surprising that you feel as you do and that your view on him has shifted over the years. (I sense you are not alone...)

      The notion of Kessel leaving in free-agency and the Leafs left with nothing but maybe a couple of playoffs appearances for his time here would not sit well indeed, Bobby- thus my thinking that Nonis will want to get something done very soon. The longer talks go toward free-agency, the more most players will want to explore that avenue.

  7. Hi Michael,

    I say do everything to keep Kessel. I've been impressed with his skill set since he came to the Leafs, and he's continued to improve in my opinion. His development, I think, foreshadows an ability to further change his playing style in the future if he does lose a bit of speed. He's not tall, compared to many NHLers, but he's strong and built surprisingly thickly for a guy with so much speed. Plus, has he ever been injured? He's still quite young, and I think he'll keep maturing and developing his grittier side with Carlyle and these Leafs. His confidence seems to be growing, and that is an important key to his potential for greater leadership.



    1. Thanks for casting your "vote" on this one, Matty! Well said.

  8. Strictly related to watching/enjoying a player and appreciating what he brings to the club, Kessel is a keeper. I also think his "I don't care" comments to the media's inane and constant questions may well suit him for continued functionality in this market.

    That said, I rarely ever heard about, thought about or cared about contracts in my youth. I only remember hearing about Keon supposedly 'not being worth a new contract' (but apparently worth controlling, so he jumped to the WHA, not to mention the $1M contract for Bobby Hull) and the other Leaf contract when Sittler got $365,000 (if I remember correctly), and I was happy for him and me, because my favourite Leaf would be staying.

    Now we've all grown 'up' and 'into' the commercial morass of a Cap World... though I believe a player of his caliber can have a workable role on a Carlyle team, I think any possibility of trading him would relate to his contract demands (term and salary).

    Without attempting to predict what might happen, I would suggest the Leafs might pony up a max term/high dollar contract, but the longer and higher the numbers go (or would 'need to go'), the more likely Kessel would be traded.

    When and how that looks has so many variables (dependent on the interest of other teams and the price they might pay) that it's impossible to cover them all quickly. Suffice to say, it could be a package deal (with Bozak) for a center more suitable to a Carlyle team or it could be for stud prospects/lottery picks at any point over the term of a new deal. It could even come this summer without a new deal in place OR a sign and trade to a franchise that wants him 'locked up'.

    The return would have to be better than we paid to get him, or there would be 'h-e-double-hockey-sticks to pay' in Leafland.

    It's not the world I want to live in for my hockey viewing pleasure (hence, I'm not really enjoying the cap and wonder if the game could still grow as the NHL may want, if a freer market was possible). However, knowing what we're up against (and can't control) may help us all to cope with what may be coming down the pipe.

    Your articles are certainly thought-provoking, Michael! My first thought was that I would be (uncharacteristically) brief in my comments!

    1. Thoughtful comment, as always, InTimeFor62.

      This question is more nuanced than some may think. Of course Leaf fans want to keep Kessel. Who wants to give away elite skill and some excitement, to boot?

      But there are so many factors nowadays, including the cap, of course. We know it will go up by the time Phil hits free-agency, but if you're going to pay a guy for 8 years and give him 8 million or more a year, you better hope he is "worth" it for at least the first few years, eh?

      The idea of Kessel leaving as a free-agent is not satisfying, thus the conundrum. Do we sign him now, at his price, or risk losing him for nothing a few months from now?

      Given the reality of modern-day hockey, signing him seems the prudent thing to do, despite the ridiculous money that will be paid. If we don't sign him before the season starts, I think they do have to look to move him. Thanks, InTimeFor62.

  9. "We know he will likely never be Bryan Trottier..."

    But he might be somewhat like Mike class shot? Won some cups too.

    Pay him!

    Kessel is entering his prime years as are many other core Leafs. A guy like Clarkson is probably at his peak. Phaneuf is 28 and isin his prime with some good years left. Lupul is 29 and probably near his peak. The time to go for it is now and over the next five years.

    No trading Kessel for prospects. We have lots of prospects. The cupboard has been restocked. We would actually have trouble making a spot for somebody if there were surprise over-performance at training camp.

    As fans, we have waited long enough. I think many fans will agree that we want to see deep playoff runs over the next five years. A first roound win is the new meassure of success. We want a second round appearance this year. We want a matchup with a weaker opponent and a win. We want a second round win and a third round appearence in the next three years.

    Some good news, Joe Colborne is putting on more weight and seems really motivated:

    On Tuesday Colborne skated at the MasterCard Centre in Toronto and his 6-foot-5 frame was noticeably larger on the ice as he scrimmaged with 18 other members of the organization.

    “I weighed in just under 222 pounds,” said Colborne. “I was around 213 when the season ended. I came in at 216 to start last year. I’m looking forward to maybe one or two pounds more, but I feel fast and strong on the ice so I’m not too worried about weight. If it comes I want to make sure it’s the good weight.”

    “I’ve said ever since day one if (the coaches) want to throw me on the wing I don’t care,” said Colborne. “I want in the lineup and to play with some good players. If it means the wing, then that’s fine. It’s a good thing to have options.”

    “I think I went a long way to show I can play at the NHL level and it’s about taking the next step, continuing to show I deserve to be up here,” said Colborne. “I don’t want to be content on coming up and being an average player. I want to continue to improve and be a go-to guy.”

    1. We need to see the kind of playoff results you are talking about, agreed, DP. Thanks for posting.

  10. I think he is a keeper.

    To me he gets better and better every year. Look at his stats over his 4 years here. Look at his playoff stats. Look at his ability to not only survive but thrive in this most demanding of markets.

    He has beaten cancer.
    Despite being shy he has figured out how to play in the league's biggest market.
    He has made us forget (or at least almost forget) about the significant cost required to bring him here.
    Nobody laughs at Kessel now like they did when he was picked last at that all star game a few years ago.
    How many more points would he have if Bozak had not flubbed on so many glorious chances?
    And now his defensive game is getting better. His compete level is getting better. He never misses a game (at least in the last 3 seasons...imagine how frustrating it would be to have a Gaborik).

    I feel like he has a quiet strength about him and seemingly a determination to overcome any obstacle. He has certainly been challenged in his young life. I think the best is yet to come and from what I have heard he likes playing here and is comfortable in Toronto.

    No brainer to me.

  11. I was happy when Brian Burke traded for Kessel. I was so desperate for a talented player to play for Toronto, I didn't get caught up in the debate on his price then. I'm very pleased with how Phil had finally gotten the monkey (Bruins) off his back in the playoffs.

    However, the Leafs can't afford to have him play out his contract here and go to free agency without compensation (ala Chris Bosh for the Raptors). Nonis needs to feel out the situation with him. Wouldn't it be ironic if Kessel left without compensation and his seemingly over priced buddy, Bozak remained?

    As much as I love having such a talented player playing for the Leafs, I don't think of Kessel as being a franchise player (yet). I'm on a fence whether to pay him like he is one because on one hand I'd like to save the money for someone who is and then again, I wonder if we'd be getting such a player in the next 10 years.

    1. You've touched on one of the real issues here, drgreg- is Phil a true franchise player, and thus worthy of the huge investment a team has to make for that kind of player? If we pay him for 8 years, what will he be in five years?

      A three-year deal would be easy. Eight years is not so easy....

  12. In the context of a 'lame duck Kessel' concern, I'm also thinking about a 'lame duck Reimer' whose contract expires at the end of this season.

    I know it's a bit different than Kessel, because it doesn't appear that Reimer really has much chance to 'recover his place in the conversation'. Reimer has probably proven his value to other teams, especially how he deals with adversity and this might just be the kicker for a team that is rebuilding.

    As I further considered our situation and wondered how another team might enter a 'win-win' trade scenario, I knew that we still need a 1C (if not now, then 'down the road'), but what if the other team needs a 1G? Reimer may not suit our management's requirements, but could be a hot commodity for another (and I'm sure the Leafs, at least, value him enough to know others probably want him.

    We seem to need a trade partner that has cap room and we probably need to release Liles. It is possible that the Leafs are almost done with Colborne as a potential top 6 Center (of course, we can only speculate).

    But I wonder what a 'hockey card trade package' of Reimer, Colborne and Liles would bring from a team whose 1G may retire instead of play for $1M.

    Of course, I mean the Flames (and Kiprusoff) who also have Kari Ramo and (former Leaf @ $925k) Joey MacDonald. Wouldn't Reimer be ideally suited to challenge for the Number 1 spot in Calgary (if not here)?

    Joey would be a good backup for Bernier (if he's gonna' inherit the No.1 spot) and gives the other Scot (McIntyre) a shot at camp to finally make the NHL.

    Of course, the big question would be, could we extract a future 1C prospect in Sean Monahan if they were getting a more developed Colborne now?

    Perhaps Calgary would want more, but if Liles consents, that would solve our apparent 'cap crisis' that so many fear is evidence of mismanagement to those who judge before the deadline!

    Food for thought, even if only to claim an idea in advance of a happening that is 'possible' :)

    I would love to be a bug on the wall during the actual internal musings and interactions of GM's throughout a trade process! Failing that, I'm wondering if you think this would be a fair scenario for both sides of such a deal, Michael?

    1. My very much at-a-distance impression of the Flames, InTimeFor62, is that they have (finally) acknowledged that they are in major rebuild mode, after desperately clinging to faint hopes that they still had a playoff team the past few seasons.

      That said, I don't know what they would be willing to give up for the type of package you put forward today. Colborne is an intriguing player, but hardly 'proven'. He may develop but it's hard to know right know. They already have a lot of "OK" NHL players. Would they give up a Monahan? I have no idea. I doubt it, though Reimer surely would be enticing for them. What's a solid young goaltender worth? Quite a lot, I would think.

      Moving Liles may be a challenge. Nice player, but a fairly big salary and he is what he is.

      Interesting scenario, however!

  13. Quick hit on a 'lame duck Phaneuf' -

    Michael, do you think the 29 year old Bouwmeester's 'reduced cap hit' (5.4M cap hit vs. previous 6.68M) signing is a good metric for comparison and a harbinger of legitimate cap reduction for Phaneuf?

    It sure seems many commenters I've seen (mostly elsewhere) think it is impossible to sign him for the same (or less) than he receives now...

    Bouwmeester is an excellent player with some 'gaps'... so is Phaneuf (even if their skills are not the same). The future may not be as cap 'fearful' as we might think!

    1. Good question, InTimeFor62. I admit I was surprised when I saw what Bouwmeeter signed for. Though he is still very well paid, obviously, the number was not as staggering as I would have suspected.

      The impact on Phaneuf? That I don't know...