Retail experts are predicting one of the most dismal holiday shopping seasons in decades this year – a crucial stretch that will set the stage for poor retail sales throughout 2009.

This week is shaping up to be another active one on the bailout-and-financing front. First and foremost, Congress returns to work this week to consider a once-unthinkable proposal: Put up billions in taxpayer-backed loans so that Detroit’s “Big Three” can be saved. Expect a fight, however, as the bailout debate finally moves past banks to focus on General Motors Corp. (GM), Ford Motor Co. (F), and Chrysler Corp.

Paulson reworks financial bailout: New targets for investment… even you can apply! Markets plummet… Bill Bonner on when stocks will be cheap enough to buy. OECD predicts global recession… Germany admits contraction has already begun. Wall Street CEOs forecast “rapid,” “deep” U.S. recession. Joel Bowman on a peculiar hissing sound emitting from the Middle East.

Even the strongest retail brands are suffering heavy losses as consumers flock to low-cost stores. Andrew Snyder says this spells doom for Under Armour (NYSE:UA). The company has a strong marketing strategy, but its sales estimates are too optimistic for a retailer of expensive niche clothing. Andrew says the stock is overvalued right now, creating a good chance for a profitable short play.

Electronics retailer Best Buy (NYSE:BBY) slashed its full-year outlook today, saying it was “the most difficult climate we’ve ever seen.” But Paul Moore says Best Buy isn’t likely to head the same way as mismanaged Circuit City (NYSE:CC). In fact, BBY should even get a lift from the bankruptcy of its main rival just before the holiday season.

Circuit City (CC) made it official on Monday and filed for bankruptcy. Only a week ago, the company announced it would close 155 stores that were underperforming. On September 29, the company reported a third-quarter loss of $239 million, which was three times larger than the loss for the same quarter a year ago.

Circuit City Stores Inc. (CC) has filed for Chapter 11 bankruptcy, a week after the struggling electronics retailer announced it would close 155 of its 566 U.S. stores by Dec. 31 and slash its workforce by 17%.

Money Map Report editor Horacio Marquez says Apple Inc. (Nasdaq: AAPL) is a bargain at today’s prices. The company continues to grow and diversify, and will keep gaining market share for its products. However, a consumption slowdown and tough competition means caution is essential when building up a position.

Circuit City Stores Inc. (CC) will close 155, or 20%, of its 566 U.S. stores by Dec. 31 and slash its domestic workforce by about 17% as the fledging electronics retailer scrambles to conserve cash and reverse six consecutive quarters of falling sales.

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