This shorting strategy defied all odds and pretty much defined the year for the stock market.

I don't know anyone who truly thought Fannie Mae (NYSE: FNM) and Freddie Mac (NYSE: FRE) would both be trading under a buck as 2008 came to close.

The idea of these once-in-a-class-by-themselves quasi-government entities that touch more than 85% of all mortgages in the United States going into full receivership by the government was considered foolish, almost ludicrous discussion that only invited serious sarcasm from professional Fannie and Freddie watchers.

The ultimate collapse of both stocks was devastating, not only to investors that continued to believe all the false headlines spewing from the front offices of FNM and FRE that said they were more than amply capitalized, but the whole financial sector as well.

The notion that Freddie and Fannie were too big to fail was a given, sucking in long-side investors at every 10-point interval on the way down to zero.

For most investors and traders, 2008 was a tough year. But while many people saw their portfolio take a merciless beating and watched their retirement vanish into thin air, there were a select few who made a killing.

In fact, if you had been on the right side of any of these bets, you could have banked enough dough to make up for your losses and then some.

Here are five trades everyone wishes they had made in 2008:

#1 Shorting 'Chindia' the day after New Year's: The Chindia experience peaked in Beijing with Michael Phelps, and the market knew it would a year and a day before the Closing Ceremonies.

#2 Getting long and staying long the 30-year Treasury bond: This strategy went from being a modestly successful trade through October to a hero-sized trade in the past 45 days.

#3 Shorting oil on the Fourth of July: The drop in oil prices has been nothing short of unbelievable. Those that had the fortitude to short crude in early July (and had the stones to stay with that trade) made a killing.

#4 Buying DryShips (DRYS) at the November low: Following its meteoric rise to $116, the stock careened all the way down to $3. But if you went long then, you saw the share price quadruple in less than a month.

#5 Shorting 'too big to fail' Fannie and Freddie: This shorting strategy defied all odds and pretty much defined the year for the stock market.

Freddie Mac (NYSE: FRE) announced today that it lost $821 million this quarter and cut its quarterly dividend from 25 cents a share to five cents a share, pending board approval. And it's paying the full dividend on preferred stock.

My question is why is this company paying ANY dividend? I know that dividends aren't necessarily just from profits like you might think. But this company lost $1.63 a share, so why is it giving shareholders even a nickel?

We all know this company may be nationalized eventually, however remote that possibility is under the current administration. We all know that taxpayers are on the hook for up to $25 billion or more for the bailout of Fannie and Freddie. And we know the Treasury can now buy shares in Fannie and Freddie to prop them up. But now it's appealing to shareholders' sense of value by keeping a dividend?

The New York Times reports that the cost to bailout Fannie Mae (NYSE: FNM) and Freddie Mac (NYSE: FRE) could hit $25 billion. But that cost dwarfs what the collapse of the real estate market might cost our country in total. I think $8 trillion is a reasonable estimate -- that's about 56% of our $14.2 trillion Gross Domestic Product (GDP).

Why are we talking about a taxpayer bailout of these two government sponsored entities (GSEs)? After all, shareholders own them but there's some vague notion that since they're GSEs, government should bailout the investors who bought their $5.2 trillion worth of mortgage-backed securities (MBSs).

So how did the government pick the $25 billion figure? It turns out that the Congressional Budget Office (CBO) doesn't know how much the bailout will cost. So it is developing different scenarios. One suggests that a bailout will cost nothing. Another suggests that there's a 5% chance that the bailout will cost $100 billion. I think this means that the bailout has an expected value of $5 billion (the chance of the scenario times its cost). Regardless, the CBO's $25 billion looks like it will be joined by an estimate that follows the Fed and OCC's look at the books of Fannie and Freddie.

Reuters reports that Fed Chair Ben Bernanke met yesterday with Freddie Mac (NYSE: FRE) chair Richard Syron and told him that Freddie and Fannie Mae (NYSE: FNM) would get access to the Fed's emergency discount window. (For those who are new to these two companies, the New York Times has a helpful graphic that helps explain them.) This is what he did to the entire investment banking industry earlier this year when Bear Stearns was headed south.

Now that Freddie and Fannie are free-falling, helicopter Ben is preparing to open the discount window to them as well. This means that these two government-sponsored packagers of mortgage-backed securities will get access to taxpayer's capital instead of going through the arduous process of trying to raise capital from private investors.

I wish I could get the Fed to bail me out when I make bad investments. This is what it means to be too big to fail. But since the Fed will not confirm the Reuters report, we will need to wait to see whether this report is true. Freddie was down 3% during regular market hours -- it had been down as much as 50% during the day. Fannie tumbled 26% during regular hours. Its stock had also been sliced in half earlier today.