In the midst of the greatest economic freefall this country has ever seen, one of the most popular topics among those in the sports finance world is which team, in which league, will file for bankruptcy first and when.

With Jeff deGraff, the top tech analyst on the Street, predicting last night on CNBC’s “Fast Money” that we are “probably in the fifth inning” of the meltdown, sports teams and their owners can’t possibly be immune, with billions and billions of dollars lost.

Let’s start with the “when.”

The best guess, according to those in the know, is that if the bear market continues, a team will likely file for bankruptcy by February or March. Who is it going to be? It’s hard to say unless you analyze every owner’s unique financial situation. But it’s generally believed that if a team files in the near future, odds are it will be an NHL team, they reason. That’s because it’s the sport with the least cash flow and probably has the owners with the lowest net worth. In fact, since 1974, a major professional sports team has filed for bankruptcy five times and every single one of them was a National Hockey League Team.

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The Pittsburgh Penguins filed for bankruptcy in 1974 and 1998, the Los Angeles Kings filed in 1995 and the Ottawa Senators and the Buffalo Sabres filed for bankruptcy within days of each other in 2003. In June of this year, Nashville Predators co-owner William “Boots” Del Biaggio filed for Chapter 11.

Although owners love their sports teams, it’s undeniable that many of their businesses are also losing money and that means, at some point, a team has to go. And once one owner does it, it’s very possible that the financially strained in the toughest markets could go running to the courthouse to try to salvage something.

Bain Capital was laughed at when it was reported that they offered $4 billion to buy the entire NHL in 2005, as the sport endured a full season of sitting out from the lockout. That deal would have put the average franchise at $133 million. Almost four years later, that number looks pretty good.