Good news: 2008 is almost over! Bad news: 2009 is about to begin. I don't mean to sound pessimistic but … er … OK, yes I do. The next 12 months will be a terrible, terrible time for some companies.

Here are 5 companies I'd suggest steering clear of in 2009:

Citigroup (NYSE:C)
I think Citi's recent trip to the bailout window for the second time in almost a month is a harbinger of what's to come in 2009. With more than $2 trillion in assets -- almost 90% of them either Level 2 or Level 3 -- supported by a sliver of tangible equity, it's no great stretch to predict that Citi will struggle to stay alive without more government largesse. After another quarter or two of spectacular writedowns, I suspect the Treasury will intervene with a bailout to end all bailouts, leaving common shareholders virtually wiped out (similar to Freddie Mac, Fannie Mae, and AIG), and auctioning off what's left of the company to healthier banks.

Morgan Stanley (NYSE:MS)
While a tremendous amount of Morgan Stanley's ills are already priced in (with shares down more than 70% this year), I have trouble wrapping my head around its place in the new, smaller Wall Street. Sure, the death of Lehman Brothers and fallout from Bear Stearns represented a hefty shakeout. But when you consider that Goldman Sachs (NYSE:GS) has an unquestionably stronger reputation, Merrill Lynch has the financial backing of Bank of America (NYSE:BAC), and JPMorgan Chase has one of the strongest balance sheets in the league, the silence surrounding Morgan Stanley's position on Wall Street is deafening.

Sirius XM Radio (NASDAQ:SIRI)
With more than $1 billion in debt coming due in 2009, and barely one-third that amount in cash, the market's resigned to bankruptcy as a forgone conclusion for the satellite radio service. However, if management can somehow finagle a debt rollover, investors could be sitting on a viable company trading for a teeny-tiny fraction of what it used to.

I guess that could happen, but with a debt market that's completely shut out anything junk-related, it seems like a fairy tale to me. CEO Mel Karmazin has said that bankruptcy isn't an option, but need I remind you that we heard similarly reassuring bouts of optimism from the CEOs of Bear Stearns and Lehman Brothers before their demises? 

If bankruptcy truly isn't an option, and the debt market refuses to hear Sirius' case, perhaps a massive outside investment that dilutes existing shareholders into oblivion is this company's last hope. While some might cling to the theory that "the most you can lose is $0.15 per share," the inner smart-aleck in me would like to remind you that percentagewise, going from $0.15 to zero is still a 100% loss.

New York Times (NYSE:NYT)
As Jon Stewart put it last night: "What's black and white and completely over? Newspapers!" You don't have to look any further than the recent bankruptcy of Tribune to see this firsthand. Of course, Tribune had a ridiculous debt load, thanks to Sam Zell's leveraged buyout, but a comparison to Times' fate isn't too far off: Both relied on outmoded business models, and both indulged in debt that only made sense when the economy was booming.

In its latest attempt to tackle the cash crunch, the Times is considering mortgaging its New York headquarters to raise cash. Hey, there's no better cure for too much debt than, uh, more debt, right?

Delta Airlines (NYSE:DAL)
Hard to believe this struggling airline -- with among the weakest cash/debt ratios of any of its peers -- has nearly tripled since July. What's behind the surge? The plunge in oil, of course. Take a company's largest operating expense, hack the price down to levels not seen in years, and Delta's prospects will naturally look rosier than they have in a while.

If you believe cheap oil is here to stay, Delta might be a steal. Me? I think oil's spectacular plunge in recent months will be remembered as a blip on the radar during an inevitable upaward march. Some see oil going as low as $20 a barrel in 2009 … pretty sweet for airlines! Of course, markets look ahead, which is where things get ugly: You'll be hard pressed to find a long-term oil projection of anything short of $200 a barrel. Considering that $147 oil nearly brought the industry to its knees, the prospect of $200+ oil should make airline investors nauseous.

Care to share any other stocks you'd avoid in 2009? Fire away in the comment section below.

For related Foolishness:

This article represents the opinion of the writer, who may disagree with the “official” recommendation position of a Motley Fool premium advisory service. We’re motley! Questioning an investing thesis -- even one of our own -- helps us all think critically about investing and make decisions that help us become smarter, happier, and richer.