Chiarelli really had no choice

Not hard to imagine Kessel making the request. Chiarelli kicked the tires on dealing him at the trade deadline in 2008 and ’09, and then felt he had him dealt to Toronto on the morning of June 26, only to have the trade fall apart later that day. It’s uncomfortable for any player to have his name bandied about so often and so publicly, and it’s probably particularly difficult for a 21-year-old.

All in all, Kessel and his agent orchestrated a clever, successful, and lucrative free agent departure, with annual salaries of $4.5 million, $6 million, 6 million, $5.1 million, and $5.4 million. When it became clear to everyone that Kessel preferred to be in Toronto more than anywhere else, including his hometown of the last three seasons, Chiarelli had little option but to acquiesce.

Had Chiarelli not swapped Kessel to Toronto for a pair of first-round picks and a second-rounder, he likely this morning would be faced with committing $27 million to a kid with 66 career goals and not much grit in his tool kit. And if Chiarelli chose not to match the presumed offer sheet, then the compensation, as spelled out by the collective bargaining agreement, would have been only first-, second-, and third-round draft picks. The potential for Brian Burke rolling out the offer sheet ultimately forced the deal, with the Leafs GM deftly, and in concert with Kessel’s stated desires, forcing Chiarelli’s hand.

No other suitor stepped up with an offer, Chiarelli also confirmed, and that was because no club wanted to yield assets to Boston and then be positioned to suffer Burke’s roundhouse right of an offer sheet. Imagine if the Predators swapped Colin Wilson for Kessel one morning, only to see him that afternoon sign the Leafs’ offer sheet? Just wasn’t going to happen, not without Kessel checking off on a sign-and-trade deal, and he wasn’t going to do that after determining over the summer that he wanted to wear Toronto’s Blue and White.

All of this has to be a cautionary tale for Chiarelli, even though he comes out of it OK now that he is armed with five of the top 60 picks in next June’s draft. No telling, of course, if he makes all those picks, because he also can convert some of that stock into roster players. If he stands pat through, say, the Olympics in February, he could end up the chief rainmaker at the March trading deadline. That’s the kind of leverage the Penguins had in the spring of ’08 when they landed elite scorer Marian Hossa and then made it to the Cup finals.

As for that cautionary tale, the Bruins ended up allowing the Leafs, with Kessel complicit in the strategy, to dictate too much of their business. Burke didn’t make Chiarelli knuckle under per se, but no GM wants to feel like another GM’s quarry or feel outstrategized. This came very close, too close for Chiarelli to be comfortable, which is a scenario he can’t allow to happen again as Milan Lucic and Blake Wheeler approach their July 1, 2010, restricted free agency.

However, there is also a key difference between Kessel, Lucic, and Wheeler. As much as Kessel ended up wanting out of Boston, the Bruins, as they demonstrated with their repeated attempts to deal him, also wanted Kessel out of Boston. The fan base won’t like either of those truths, saying the kid would have been easier to sign if he had been shown more love. Who knows? His agent, Wade Arnott, did not respond to an e-mail.

By allowing it to play out, the Bruins came to an organizational decision that Kessel’s overall game wasn’t enough to justify paying him as an essential member of the team. The salary cap allows only so many core players. Here in the Hub, Kessel was not deemed to be one of them.

Remember, they drafted Kessel, paid him very well, brought him along, coached him, and simply weren’t convinced he was the real deal (contrary to much of the fan base). If he turns out to be one of the game’s few elite goal scorers, they missed the mark, badly. If he turns out to be someone more like, say, Maxim Afinogenov, then they just made a very shrewd deal, one that has given them the assets that could be turned into goodies for a long Cup run or transformed into high-end prospects.

Argue what you will over the decision to let Kessel go, or how it played out under Burke’s clever hand, but there is no arguing that the Bruins now own a bounty of draft picks that allows them multifold opportunity to manage the cap more efficiently and mold their roster.

If nothing else, all of it also demonstrates that Chiarelli oversees a management team that has a specific, defined way it wants the team to play, identifies who can and cannot execute within that definition, and then has the conviction to live with the consequences. Maybe you don’t like the plan, but it’s a plan, and that has not always been the case on Causeway.

Orr & Co. to stage ’70s show at Fenway?

The league figures the ice should be ready to go by approximately Dec. 18-20, and Jacobs said during Thursday night’s Town Meeting that he’d like to stage an alumni event in the days leading up to Christmas.

A couple of issues here: 1. Given other civic and charity plans, possibly even public skating, the base paths could be a bit crowded to work in an event of this scale. 2. If it’s not a charity gig, the NHL could raise an objection to a large-scale pay event being staged on its sheet prior to the Winter Classic.

All that said, it would be one fine sight to see Bobby Orr, now 61 years old, take a skate through the Back Bay. Imagine the memorabilia shots of No. 4 cruising through open ice, with the Green Monster in the background.

Etc.

Kevin Paul Dupont can be reached at dupont@globe.com; material from personal interviews, wire services, other beat writers, and league and team sources was used in this report.