Why tackle just one tired Internet topic when you can tackle two? It's Ilya Kovalchuk AND Rick DiPietro time!
Topic fatigue aside, it's worth addressing something that has come up in all the Kovy hysteria: This didn't start with DiPietro. I mean, sure, maybe crazy-long deals started with DiPietro (but not really; Yashin's gratuitous 10-year whopper came before that). Maybe the first long-term deal with an eye toward managing the cap started with DiPietro. But that 15-year, $4.5 million-per-year deal was not a cap circumvention. (Nor was Ovechkin's, though that's been dragged into this drama too.)
What was it? A compromise between player and owner* -- as opposed to the rejected Kovalchuk deal, where each party has their cake and eats it too (assuming Ilya's allergy to backchecking does not spoil the Devils' cake), paving the way for league rejection and even the fanciful L.A. dream of re-entering the pursuit.
Because in DiPietro's deal was an implicit compromise:
The Islanders paid him more than an RFA and not-quite-prime #1 goalie would make in the early years, in return for his long-term commitment and in return for paying him less than a #1 goalie would make during his peak years. In current terms, the Islanders "bought his UFA years" (though of course in the Isles case, they bought a whole ton of 'em. But that's another matter that has little to do with the cap).
* The DP deal is commonly ascribed to Charles Wang, not the GM -- as was the Yashin deal, as outlined in the Hahn/Botte book, "Fishsticks"
Each side took on risk, but it was not risk that could be evaded by making the deal go to age 40 instead of age 38. It was not risk mitigated by tacking on meaningless years at laughably low salary, nor by picking a lower salary in the first two years to rig a way around the CBA's "50% rule."
The risk DiPietro took on was that salaries would continue to rise and he would be making "only" $4.5 million in a world where franchise players make twice that. This is the risk that every player takes when he signs a long-term contract. (i.e. "What if revenues double, and suddenly I'm underpaid?! Suddenly the long-term security I bought seems regrettable!") Further, if he elected to retire before the deal was up, he was out $4.5 million per on whichever years he left on the table. This was not a Kovalchuk scenario, where Ilya is protected from early retirement -- almost rewarded for early or rather "normal" retirement -- by a laughable minimum salary during the final Chelios years of the deal.
The risk the islanders took on was that DiPietro might not reach that peak, or worse-case scenario (that never happens, right?), that he would meet the peak but then suffer injury- or age-fueled decline -- which every player meets at some point -- well before the contract was up. The Islanders compensated for DiPietro's potential loss of peak-year earnings by overpaying him in the near-term and, most likely (but not certainly, when you consider Dominik Hasek then and Dwayne Roloson now), overpaying him in his declining years if he became just an average Vanbiesbrouck in his late 30s.
In short, the Islanders took on a big risk by committing to DiPietro for so long; the Devils -- had the deal been approved -- actually benefited from extending their sham commitment to Kovalchuk for so long.
A Different Kind of Madness
I've said a hundred times that a 15-year deal with a goalie was a foolish risk, even if you're securing a "face" of the franchise. But if you want to take that risk -- if you have a crystal ball that says this man will continue his ascent to the #1 position and stay there through his late 30s -- then $67.5 million is hardly a ridiculous amount for 15 years of #1 goalie earnings, given the environment and direction of salaries at the time.
But that's the thing: There was no cap benefit to the Islanders if DiPietro retired early. They do not save on the average annual cap hit, hence whether he retires at 31 or 40, the cap hit for the years he played -- I use "played" loosely, given the last two seasons -- is the same as the average annual salary he earned in those years.
There are arguments that teams should be allowed to include declining "tails" at the end of stars' long-term contracts. (After all, how much is Doug Weight worth today versus what he was worth 10 years ago, when his salary hit $9 million?) There are arguments that teams and players should be allowed to bet on diminishing, but still playable, years at the end of their careers -- and even take the cap benefit that comes with signing on for that now.
But this envelope-pushing, cap-circumventing game that carried from Miikka Kipursoff's extension all the way through Hossa and to Kovalchuk's theater of the absurd 17-year deal? It didn't start with the DiPietro deal. No, that was a madness of a different kind.