Dave Nonis completed arguably the best and most important contract negotiation of the offseason this morning, as the Toronto Maple Leafs locked up star right winger Phil Kessel to an 8-year contract worth $64-million. The annual cap hit it comes to a round $8-million, shirking the annoying trend of players getting paid their Jersey number, and is the biggest and most expensive player contract ever signed by the Leafs, nearly doubling David Clarkson’s contract signed in July.

Kessel's 26th birthday is tomorrow. $64-million is a heckuva present… — James Mirtle (@mirtle) October 1, 2013

Kessel's extension AAV with TOR will be $8M. There's a signing bonus up front and another one in what would be a potential lockout year. — Bob McKenzie (@TSNBobMcKenzie) October 1, 2013

As of this writing, Phil Kessel will have the eighth highest cap hit in the National Hockey League next, behind Ovechkin, Malkin, Crosby, Perry, Staal, Giroux and Getzlaf (though that will change with 2014 free agency). This also represents one of the first long term contracts signed by an elite player under the CBA and the new 8-year contract limit, which has changed the nature of these deals insofar as extending the term of the deal and back-diving the salary in the later years is no longer an option in order to reduce cap hit.

So what have the Leafs purchased for $64-million? Quite a lot as it turns out. In the past two seasons, only Evgeni Malkin, Claude Giroux and Steven Stamkos have tallied more combined points than Phil Kessel’s 134. He and Stamkos are the only players to have cracked the top 10 in scoring the last two years. Since the time of his trade to Toronto back in 2009, Kessel has scored 119 goals. That total puts him behind only Alexander Ovechkin, Stamkos, Corey Perry, Patrick Marleau, Jarome Iginla and Ilya Kovalchuk over that span. All of those players save for Stamkos are older than Kessel, and are signed to big-money deals themselves.

Did the Leafs get any sort of bargain on this deal? No, not really. The Leafs had the pay the piper, and were smart to do it now rather than take on the risks that are associated with leaving the winger unsigned until May. While perhaps imprudent, had Kessel hit the open market, who’s to say a team wouldn’t have been willing to offer him close to $64-million over seven years? While unprecedented, the new CBA regulations are (somewhat) forcing teams to pay market value for a player. Clearly, the Leafs respect Kessel’s wishes not to negotiate during the season and got the deal done to secure its best player.

The weight of expectation certainly doesn’t get any lighter from here on out for Kessel. The same media that wanted to remind us all of the trade that brought Kessel here during each of his “slumps” will be the same ones constantly questioning whether or not Kessel is justifying his pay stubs. It might seem all bright and cheerful, now…

Every contract signed by every star seems too long and too much. But when you view the market and do the math this is fair value for Kessel. — steve simmons (@simmonssteve) October 1, 2013

But eventually, fair weather comments like these will give way to less fair criticisms should the Leafs or Kessel falter.

Regardless, Phil Kessel is going to be around for the next 9 years, and the franchise is stronger in the future with today’s efforts. However, in the process of locking up their star and the augmentations this offseason, the Leafs will still need to be wary of the salary cap. With the Kessel extension, the Leafs will have maybe as much as 30-million in cap space available for 12 roster spots. That might sound like a lot of wiggle room, but the Leafs are sure to re-sign some of their significant number of pending free agents. Re-signing more than a couple of Phaneuf, Reimer, Kulemin, Gardiner, Franson, Raymond, Ranger, Bolland or McClement and the Leafs are right back into cap hell. On the other side of that coin, with the extension, the Leafs now have 5 of 6 positions on the top two lines secured long term, as now Kessel, Lupul, van Riemsdyk, Clarkson and Bozak are signed through 2018.

One nice way of looking at it is to think of the erasure of the Armstrong and Tucker buyouts ($2 million total) as well as the retained salary on Frattin and Scrivens (500k) almost exactly covering Kessel’s raise for next season.

Regardless, the extension was the right move, and the money could have been worse. Let’s see what the $64-million dollar man can do tonight as he, his oversized wallet and the Toronto Maple Leafs make their 2013-14 season debut against the Montreal Canadiens.