(1) Rick DiPietro v. (4) Vincent Lecavalier

With Alexei Yashin's narrower-than-expected victory over Marc Savard, all four of the semifinalists are now set, and each of the top four seeds has advanced without too much problem. Today, we start those seminfinals with Rick DiPietro taking on Vincent Lecavalier in a truly epic match of inefficient spending. Lecavalier's deal isn't as famous as DiPietro's first round opponent, Ilya Kovalchuk, but I think it should provide a stiffer test. After the jump, I'll make a case for each player.

Rick DiPietro's seems like it will never end. The Islanders will be paying him for at least the next decade (and maybe two if they decide to buy him out), and while his never-ending string of injuries might soften the blow for some teams (who could stash him on LTIR and keep on spending), the Islanders are a budget team, and that $4.5M is gone whether DiPietro is playing or not. There are, so far as I can see, three main ways to get rid of this contract. The first is through trade. I understand that this contract would be very difficult to move, but no contract is ever untradeable if you're willing to give up enough to get it done. The club would be asking a team to take on, essentially, $45M of dead money over the next several years. Presumably, some of that money could be taken up in the awful contract coming their way in the trade and the rest would be made for in good players and prospects heading the other way, something like Rick DiPietro, Nino Niederreiter, and John Tavares heading to Toronto for Mike Komisarek. It's not likely to happen, and would be extremely damaging to the franchise, but it's not impossible either. The second way out is through retirement. This strikes me as being unlikely since it involves DiPietro giving up a tonne of money, but with every passing year, it becomes a bit more possible. On the downside, if he retires due to injury, he gets paid in full. And that brings me to the third way, a buyout which reduces the cost to $30M over twenty years, and in my opinion, probably represents the best way forward.

Vincent Lecavalier

Vincent Lecavalier's deal may not seem as bad as DiPietro's at first glance, but there are some things here worth considering. A buyout of Lecavalier's deal in the summer would actually be more expensive at a total of $43.3M over eighteen years. It would also make a huge mess of Tampa's cap in the future since the cap hit would be tiny for the first six years, then huge for the next three (including one year at over $9M), followed by nine years at just over $2.4M. It would seem to me, then, that a buyout isn't really a realistic option. There's also virtually no chance that Lecavalier retires any time soon, and his NMC makes him nearly impossible to trade. With DiPietro, at least there are options. With Lecavalier, not so much.  If we assume that Lecavalier is going to play out at least the next six years of his deal, and that the number that matters in Tampa is real dollars, and that the Islanders decide to buy DiPietro out this summer, then Lecavalier's deal may actually be worse. DiPietro would cost his team $30M, but it would be spread out in equal installments over 20 years, and I shouldn't need to tell you that $1.5M in 20 years isn't going to be worth nearly as much as $1.5M now. Lecavalier, by contrast, will likely cost his team with inefficiency immediately. Over the next six seasons Lecavalier's play is very likely to decline since he's turning 31 this April, and it's not like he's earning that contract now. What will his average value be per season over these next six seasons? Is $4.5M per season a reasonable estimate? If so, that's an extra cost of $31.5M in just six years. There's a very real chance that this deal actually ends up being worse.

The Bracket