It’s day 1 of the post-Phil Kessel era.

Yesterday’s return seemed reflective of a negotiation that involved only one serious bidder and a Leaf management group that had self imposed a hard deadline by deciding Kessel had to go now. The Penguins aren’t an ideal trading partner for the Leafs in the least, with low to very low first round picks (probably the case for most interested teams) and more importantly a fairly weak prospect pool. Kessel’s control over where he goes may have affected things here, but he had the option to revise or expand his list, or approve any deal presented to him.

Even with all that in mind, this seems like a veteran GM gaining the clear edge on the Leafs for a few reasons.

  • There isn’t one piece of young talent with a measure of NHL proven-ness coming back. While former 22nd overall pick Kasperi Kapanen certainly has promise worth noting, it’s been reported that the Leafs got the fourth best defence prospect in the Penguins prospect pool, according to the Penguins internal ranking. That may be post-trade spin, but Harrington is certainly not ahead of Maatta or Pouliot.
  • Despite the fact that they were arguably not receiving a true high end prospect / young roster player, the Leafs gave back a second round pick in a deal for a picks and prospects-oriented return.
  • The first round pick is lottery protected if things go sideways in Pittsburgh this season. If you’re adding Kessel to a group that includes Crosby, Malkin, Letang, Fleury, Maatta, Perron, Hornqvist and Kunitz, you better be making the playoffs, and yet the Leafs gave the Pens protection should they somehow not qualify.
  • They retained salary: 7 years x 1.25 million.
  • It’s not a big deal, but in addition to retaining salary, they took back $2.2 million of salary in the form Nick Spaling to further facilitate the deal. With the salary retention, the Penguins are getting Kessel at a $6.75 million price point for the duration of the contract, and with Spaling’s inclusion, they’re effectively getting him at $4.55 million in 2015-16. Maybe Spaling will prove effective, and at a minimum it won’t affect the team besides costing MLSE money (they also ate Kessel’s $4m signing bonus), but it’s surprising the Leafs had to grease the wheels to this extent just to get it past the finish line.

It’s no wonder Rutherford couldn’t hide his smile and stopped just short of proclaiming a trade win right in his press conference. The Leafs didn’t make this trade all that hard on him. The Pens are adding the elite scoring winger they’ve been dying for with little upfront cost. As far as any sacrifices in this deal, we’re talking ‘maybes’ years down the line, and even then, they’re going to be confident they’ve gotten far and away the best player in the deal at a great price ($6.75 mill).

The hope from the Leaf perspective will be that the return grows into something more than it seems to be today; Shanahan admitted that the work starts now for the Leafs in making sure that it does.

This Leafs management group has been applauded for a string of sound moves over the course of the past calendar year, leading up to the recent 2015 draft that’s received positive early reviews. This is their first major move at the helm, though, and it makes you ask some questions about the dynamics of the front office and how trade negotiations are being handled.

Just the other week, it was reported Brendan Shanahan let it be known that Kyle Dubas was the Leafs’ point man for trade negotiations. Then, in his press conference yesterday, Shanahan talked about the process he went through (using the word “I”) negotiating with Jim Rutherford on this trade for the past month or so.

At the end of the day, there’s always hope in mystery boxes and hopefully a few pieces from this deal really pan out, but the Leafs traded a fantastic scoring winger knowing he couldn’t be the centerpiece of a Cup team without the right centers and defencemen around him — and didn’t get a piece back that has much hope of addressing either of those needs.

The best guess one can gather on how Leafs management is viewing this – they’re loading up big time for the 2016 draft (11-12 picks already), moved Kessel and his contract for whatever they could get in terms of picks and prospects, and plan on getting what they need through the draft. They’ll need to do a better job drafting and developing than they have with trading their best asset.

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