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!


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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…..