Saturday September 19th, 2009

Time was that a Boston fan's second-favorite team was whoever happened to be playing the Montreal Canadiens that night.

Now they'll be pulling for anyone lining up against the Toronto Maple Leafs ... even if it means cheering on those hated Habs.

That's because every Leafs loss this season and next adds value to the trio of high draft picks the Bruins acquired late Friday night from Toronto in exchange for the rights to winger Phil Kessel.

Shortly after sending Boston a first- and second-rounder in the 2010 draft along with a 2011 first-rounder, the Leafs inked Kessel to a five-year deal worth a reported $27 million.

Safe to say it was a risky move for both teams.

Unable to sell the restricted free agent on the merits of a cap-friendly contract -- something on the order of the three-year, $11.25 million deal signed earlier this summer by the superior David Krejci -- Bruins GM Peter Chiarelli had no choice but to move Kessel. Don't expect too many tears in Boston, though. The fifth overall pick in 2006 chafed at the imposition of Claude Julien's strict defensive scheme and lacked the grit required of a Boston winger. Still, his world-class speed and the Brett Hull-like ability to find dead space from which to launch a nasty snapper can't be replaced by anyone in the Bruins system.

He's coming off a breakout season in which he scored 36 goals and 24 assists in 70 games and, at just 21, Kessel's not yet reached his ceiling. By sending him to a divisional rival, Chiarelli risks being haunted by his decision at last 30 times over the next five years.

There was method to his madness, however. By accepting draft choices in exchange for the malcontent, Chiarelli kept the B's under the cap this season, if only barely. And by refusing to make a high-dollar, long-term commitment to Kessel, he left himself some wiggle room next summer to accommodate first line center Marc Savard and/or the demands of the next set of cornerstone RFAs, including Milan Lucic, Blake Wheeler, Mark Stuart and Tuukka Rask.

Those are important considerations -- but are they important enough to compensate for the fact that the Bruins just lost a legitimate first-line winger and could end up with nothing to show for him?

It's true that, along with the 2010 Tampa Bay second-rounder acquired last April in the Mark Recchi deal, the B's now have eight picks spread over the first two rounds of the next two drafts. That's the sort of cupboard stocking potential that can ensure a team remains a perennial contender in the cap era. But the Bruins have to make the right choices to ensure a fair return on this deal ... and considering their last three drafts received middling reviews and have yet to generate a single game played, that's hardly a fait accompli.

Chiarelli could decide to bundle the picks to move up in the draft and improve his odds of success, or dangle them as part of a package to acquire an impact player ahead of the trade deadline. Whatever he does with his booty, it's fair to say we're unlikely to get a real handle on how well Boston made out in this deal for several years. It's an equally mixed bag from Toronto's perspective.

Brian Burke's four-month courtship netted him the best player in the deal, the dynamic, young sniper the Leafs desperately needed, and he did it without sacrificing anyone off his roster -- a significant consideration for a man determined to return Toronto to the playoffs this season. In Kessel, the Leafs add a preeminent gamebreaker -- a nice get given that they lost 13 games after the third period in 2008-09, second-most in the league.

But Kessel also is a player with just one solid season on his resume, a player whose singular move when entering the offensive zone with the puck has become far too predictable and easy to defend, and who relies on a set-up man like Savard to create most of his opportunities. And while he has plenty of time to mature over the course of his new contract, there's no denying that some of his former teammates quietly questioned his commitment to the cause.

Think about that. It wasn't an oversight by the Bruins that led to their cap space being filled before their leading goal scorer was accommodated. They simply believed he wasn't as valuable to their future as some others.

Focusing on the present allowed Burke to assess Kessel's value differently. He continued a rebuilding shortcut that suggests the Leafs will ice a more competitive side this season, but in doing so he ensures Toronto's scouts will spend the next two drafts picking through the leftovers after all the blue chips have been scooped up. That's a steep price to pay, even for a team that re-loaded the prospect cupboard with college free agents this summer.

The only real certainty here? With a new jersey on his back and a fat contract in hand, Kessel clearly comes out on top. Whether Toronto or Boston joins him in the winner's circle at some point is yet to be determined.

SI Apps
We've Got Apps Too
Get expert analysis, unrivaled access, and the award-winning storytelling only SI can provide - from Peter King, Tom Verducci, Lee Jenkins, Seth Davis, and more - delivered straight to you, along with up-to-the-minute news and live scores.