Wang loses his gamble with DiPietro

I have a friend who is a gambler. In addition to college and pro football and basketball, he's been known to put money on U.S. Open women's semifinal matches. That's hardcore.

Like most gamblers, he'll tell you all about his winnings, the three-team parlays and close covers, and then little or nothing about the bad beats. But that's the gambler's prerogative. You always want to believe you're up more than you really are.

Charles Wang would like to have that luxury now that it is becoming increasingly clear that the Rick DiPietro signing was a bad gamble. The bad beat of all bad beats. A bust.

The Islanders announced this week that D.P. will be shut down for the season because "surgical swelling" in his knee has not subsided. This after taking a particularly conservative approach where he did not play a game until January 10. He made it through only eight games, and has appeared in only 13 in the last two seasons.

Critics of the 15-year contract between DiPietro and the Islanders have been legion, and to their credit, they've been slamming the deal since before the ink was dry. Media, fans, unnamed hockey executives -- they couldn't understand why in God's name Wang would commit himself to a deal so big the player would be immovable.

But Wang does things his way, and at the time he needed a marquee player to build his team (and promotions) around. D.P. fit the bill. He was young, a budding star with matinee-idol looks and a game to match.

Why 15 years? Why not 10? Or even eight? Only Wang knows for sure. And, maybe Mike Milbury, who reportedly put the bug in Wang's ear about inking D.P. long-term. After all, it was Milbury who traded Roberto Luongo and drafted DiPietro with the first overall pick in 2000, instead of Dany Heatley or Marian Gaborik. I know, it's painful to think about. (By the way, Ilya Bryzgalov of the Ducks went No. 44, and the rest of the first three rounds produced almost no one.)

Wang defended the length of the deal by pointing out that the annual salary was just $4.5 million, so if DiPietro turned out to be a top-level goalie, it would actually be a bargain.

Wang, who likes to think he thinks out of the box, rolled the dice. At the time, DiPietro had no injury history to speak of. The year before he signed, he played 63 games. The next season, 2006-07, he played 62, and the following year he played in 63 and made the All-Star team. Had he followed that same trajectory, the deal would have been justified.

But we know what happened. Hip surgery in March 2007. An injured hip at the All-Star skills competition in 2008. Another hip surgery the following month. Knee surgery three months after that, followed by another knee surgery in November. Five games played in 2008-09, a long layoff to recover, and then eight games this season.

That dice roll came up snake eyes.

We assume (and hope) that the contract is insured, because we know it is guaranteed. If DiPietro retires due to injury, he gets paid. If he retires at any point for other reasons, he forfeits the remainder of the deal.

Personally, I wasn't a big critic of the deal. I wouldn't have done it myself, but I understood -- to a degree -- Wang's logic. DiPietro was his best player and he needed someone to focus the marketing on. There was no reason to think that he would get hurt the way he did, except this is ice hockey, and players do get hurt. A lot.

Garth Snow said he expects DiPietro to be ready to go next season. What else is he going to say? DiPietro insists that he is in the best shape of his life -- except, of course, for those darn knees. He said he's just following doctor's orders.

For his part, Wang is learning that when you gamble in sports, you can't hide the bad beats. Sometimes you win, sometimes you lose, and when you lose, everyone knows about it and won't let you forget it.

As a fan, I can only hope that DiPietro comes back healthy, but like most fans I don't expect it. In all likelihood, the D.P. era is over and the contract will go down as one of the worst in NHL history, right alongside the one the Islanders signed with Alexei Yashin.

That's the kind of history we don't need.