Looking at the two major deals with the Bruins, with 20-20 hindsight: A Cup in hand, who has the better future?

In recent days I've posted on what for me are some very positive Leaf thoughts, including memories about why many of us became Leaf fans in the first place and why the Leafs still matter after all these years- and all this losing.

But every once in a while, I seem to feel the need to indulge in a rather sobering assessment about being a Maple Leaf supporter for more than fifty years.  That's a long time.  It's great, and sometimes necessary, to look at the glass as half full.  But at the same time, that's not always the way things have been, or are.

So I've been thinking in recent days about the Leafs and the Bruins, who are, as we all know, two Eastern Conference clubs, and long-time (I think we can say legitimate) rivals, dating back to the great "Original Six" days.

What I've been re-processing is this:  those two big trades between the Leafs and the Bruins, that saw Kessel arrive here, what turned out to be Seguin head there, and of course the more recent Kaberle deal which brought some significant prospects back this way.

I suppose the fact that the Bruins won the Cup (out of what I thought was a relatively weak Eastern Conference; I'm still a bit stunned) last month no doubt was a trigger for why I was even thinking about the trades.  I wonder, too, how many times in recent history that two teams have made what can fairly be described as two separate huge trades with each other—within only 18 months?

When the Leafs sent two number-ones and a second-rounder to Boston for a proven young goal-scorer in Phil Kessel prior to the 2009-’10 season, we all knew it would be a trade talked about for years. It was that kind of trade.

Much the same can be said of the Kaberle move.  He went to the Bruins—and despite the many rumors I didn’t think Burke would ever send him there.  But he did, and Toronto got a nice return in young Colborne (a former first-rounder himself, already with AHL experience in hand) a second-rounder which has turned into John-Michael Liles and the 30^th pick in this year’s draft, which was part of moving up to get Tyler Biggs.

So it’s hard to argue with the fact that the Leafs end up with some elite talent (Kessel), a legitimate prospect/near NHL-ready player in Colborne and a first-rounder (Biggs) as a result of these two big trades with Boston.

The flip side of that ‘half-full’ glass is that the Bruins may have an even better story to tell after the deals.  They have already won a Cup, and I’m not sure they would have done so without Seguin.  (Whether they would have done it with Kessel is another debate...) Why?  Yes, I know he was in the press box a lot, but he gave them a huge boost just when they needed it, after sitting out most of the early part of this past spring’s playoffs.

As for Kaberle, well, I won’t argue that he was a huge difference-maker, or in any way indispensible to Boston’s cause down the stretch or in the playoffs.  There is no question they had precious little confidence in him.  He never killed penalties and rarely played key minutes. (In fact his minutes were very limited, ranging between 12 and 18 minutes most nights in the playoffs—and way less in Game 7 of the finals.)

But he did play his (albeit modest) minutes.  He was a plus 8 in the playoffs, and chipped in offensively on occasion.  He was a 5/6 defenseman by the end, but he did contribute.  If he had not been in the lineup, the Bruins were woefully thin behind him on the blueline.  He did fill a void, albeit one that was farther down the depth chart than had been anticipated when they made the move.

So would the Bruins have won without he and Seguin?  I’ll say no. Not because they were consistently big impact guys, but simply because they both made the kind of minor but valuable "depth" contributions that are necessary for winning teams.

And, importantly, the Bruins have Seguin for years to come, just like the Leafs have Kessel.  And while the Leafs have Colborne and Biggs, the Bruins also selected (by all accounts) a much coveted young defenseman with the 9th overall pick (Toronto's) in this past June's entry draft.

So they too will have “prospects” for years to come, with what they got from the Leafs.

So here we have it:  a Cup, an elite young player and good prospects for an elite young player and good prospects (the Leafs with more of the good young prospects...)

Who “won” those deals?  In isolation, the Leafs have certainly "won" the Kabby trade over the long haul.  But even if the Leafs win a Cup someday with the guys they got from the Bruins, they’ll still only catch up to what Boston has already in their hip pocket.

That's the sobering part.