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Yesterday, the New York Rangers pulled the trigger on a buyout many had long since called, literally from the day after the initial signing occurred: “Within a few seasons, Brad Richards will join Drury and Redden as a cap casualty, both of whom had their career reputations damaged by the horrible contracts handed to them by the New York Ranger franchise.”

It was widely known Brad Richards always wanted to go join John Tortorella and play in the Big Apple that summer, but naturally I harken back to Brian Burke’s philosophy against these monstrous back-diving deals that were loophole’d in the last CBA. Should Richards retire before the 2018 season, from 2018 to 2020 the Rangers will be hit with a $5.66 million annual cap penalty due to the new CBA’s recapture clause. Devastating.

It next makes me think about the buyout suicide it would require to expunge the David Clarkson contract. There’s little doubt a player of Clarkson’s ilk (from his Jersey days, anyway) would tick a lot of boxes for Brian Burke in terms of what he likes in a player, but it makes me wonder how Burke approaches that same negotiation. Does he draw the line at 5 years, his self-imposed contractual length limit that applied to all but the elite players of the League? Does he go back to Clarke MacArthur, who was his best-value UFA signing and continues to provide good value for his contract in Ottawa, with an offer when he finds out the term demands of Clarkson’s camp?

By this point these are pretty worthless questions riddled with hindsight bias, but a) it’s not like we have real Leafs news to talk about, and B) at this time of year, there’s relevancy in at least talking about these deals and learning from the history. The Leafs have made so many mistakes on July 1, going back to Blake, Finger, Komisarek, Armstrong, etc. The list winds on, and as much as we can say Burke was onto something with his admonishment of cap-circumventing deals as well as stupid-long term deals in general, it was Burke who signed some of those overpayments. Real solutions exist rarely in the form of big contracts in unrestricted free agency, but it’s certainly the case if management overpays for mediocre talent.

Jonas Siegel had a good quote on this on the radio yesterday: “I look at some of the better clubs in the NHL, and when they do spend on free agency 1) they spend on skill. Look at Marian Hossa for the Blackhawks. On July 1st they signed Hossa to a massive deal. Granted, that could come back to haunt them a little bit, but they got a couple Cups and they paid for skill.  If you’re going to pay in free agency, you’ve got to pay for high-end skill. I think one of the problems in Toronto with the Leafs is that they’ve paid average players on good contracts and they’ve paid good players on great contracts. They’re always in a situation where they’re paying for what the player isn’t… It just creates so many problems in the cap era.”

Leafs management shouldn’t let the Clarkson contract make them completely gun shy if there is a legitimate opportunity to dole out big money on an actual high-end talent, but that requires identifying the key difference Siegel is talking about (see: Stastny, Paul vs. Bolland, Dave). The inability to do that has hurt this organization throughout the succession of four straight general managers.

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Alec Brownscombe is the founder and editor of MapleLeafsHotStove.com, where he has written daily about the Leafs since September of 2008. He's published five magazines on the team entitled "The Maple Leafs Annual" with distribution in Chapters and newsstands across the country. He also co-hosted "The Battle of the Atlantic," a weekly show on TSN1200 that covered the Leafs and the NHL in-depth. Alec is a graduate of Trent University and Algonquin College with his diploma in Journalism. In 2014, he was awarded Canada's Best Hockey Blogger honours by Molson Canadian. You can contact him at alec.brownscombe@mapleleafshotstove.com.