What would happen if a brilliant hedge fund manager took over a retailer and ran it with a rigid focus on financial metrics, putting aside all that soft stuff about branding and marketing?

Take a look at Sears Holdings (NASDAQ: SHLD), and you have your answer. While macroeconomic trends haven't exactly been the company's friend, the stock has plunged from close to $200 per share in early 2007 to its current price of $66 per share. Just a few months ago it was trading in he mid-$20s.

The Wall Street Journal reports (subscription required) that short-sellers are having an impossible time locating shares of Sears Holdings (NASDAQ: SHLD) to borrow. Chairman Eddie Lampert controls about half of the company's stock through his hedge fund, making the shares difficult to borrow. For investors who are able to locate the stock, borrowing costs are running somewhere between 30% and 40% per year.

Given the difficulty short sellers are having, it seems likely that shares of the company are trading at a higher price than they would were the stock more liquid.

On the other hand, 29% of the company's float is currently sold short at those steep interest rates, indicating that a big chunk of investors are incredibly confident that Sears shares have a lot farther to fall.

This post is part of our feature on Money Losers of 2008. See all 20.

There's no doubt about it -- times are tough. People are struggling to find work and to pay the bills as the value of their homes and savings dwindle. The poor get poorer, and the rich get richer.

Or do they? It's all relative, of course, but world's billionaires have been taking some big hits too. We take a look at Sheldon Adelson, Kirk Kerkorian, and Lakshmi Mittal in their own separate posts, but here are some other billionaires who have lost billions this year (courtesy of Forbes and Business Sheet).

• Brothers Anil and Mukesh Ambani of India's private conglomerate Reliance lost $32.5 billion and $28.2 billion, respectively.
• Warren Buffett, the Sage of Omaha, lost $16.5 billion. Shares of Berkshire Hathaway Inc. (NYSE: BRK.A) are down about 32% since the beginning of the year.
• Microsoft (NYSE: MSFT) founders Bill Gates and Paul Allen lost $12.3 billion and $2.6 billion, respectively, while CEO Steve Balmer lost $6.5 billion. Shares of Microsoft are down 46% since the beginning of the year.
• Larry Page and Sergey Brin, cofounders of Google Inc. (NYSE: GOOG), lost $11.9 billion and $11.7 billion, respectively, and CEO Eric Schmidt lost $3.8 billion. The share price of Google has fallen 55% since the beginning of the year.
• Larry Ellison, CEO of Oracle Corp. (NASDAQ: ORCL), lost $8.2 billion. Shares of Oracle are down 21% since the beginning of the year.
• Media maven Sumner Redstone lost $7.2 billion. Shares of his private investment firm National Amusements fell 70% this year.

The chain that once dubbed itself "where America shops" is increasingly a place shoppers avoid. Despite its much-publicized recovery efforts, investors should consider steering clear, too. Sears Holdings Corporation (NYSE: SHLD) has been in the news a great deal lately, announcing awful sales results and planning yet another stock buyback to prop up its flailing price.

The recent store changes have not worked, and neither will the financial engineering. This company is on its way down, and a visit to a local store showed me why.

Sears used to be the General Motors (NYSE: GM) of retailers -- an apt analogy when both were all-American giants, and just as apt today as both struggle. Sears had completely lost its way when vulture investor, Eddie Lampert, bought the company in late 2004 and combined it with Kmart. Wall Street analysts went nuts, pushing the stock price to $192 a share.

Today, Wall Street has lowered that price to near $40.

This post is part of AOL Money & Finance's Best & Worst in Money 2008 feature.

There have been big hopes for all the nominees in this category at one time or another, but they've also suffered from questionable management moves of various sorts. So what's to root for in any of these companies?

Circuit City was founded in 1949; back then it was known as Wards Company. The big-box format and Circuit City name came as the result of a series of retail experiments, and became official in 1984. The company was listed on the New York Stock Exchange in the same year. In 1991, the company established a bank to operate its private-label credit card, and later offered a co-branded Visa. Big-box used car retailer CarMax (NYSE: KMX) was also owned by Circuit City at one point. In 2005, the company's board rejected a buyout offer; the company was worth a reported $1 billion then. The next year, Philip J. Schoonover became chairman, and ... well, the rest is history. Circuit City is now in Chapter 11.

Citigroup (NYSE: C) was formed in 1998 from one of the largest mergers in history: banking giant Citicorp and financial conglomerate Travelers Group. The company holds over 200 million customer accounts in more than 100 countries, and includes the investment services brands Smith Barney and Primerica. The company owns prominent, renowned buildings in Manhattan and Chicago, and also won naming rights to the new ball park of the New York Mets. But it was the subprime mortgage crisis that was Citigroup's undoing, resulting in the need for the recent federal bailout.

Sears (NASDAQ: SHLD) is scheduled to report earnings for the third quarter on Tuesday, December 2. The expectation is for a loss of $0.49 per share. I think it's therefore safe to say that the retailer won't be turning a profit.

Sears has been one awful retail story as of late. Actually, just about every retailer has been awful as of late. It's no surprise, of course, considering the economy. But Sears has been experiencing challenges even beyond what can be explained by the economy. The company has been missing estimates, same-store sales haven't been great, and if you take the time to talk to people about Sears, or if you follow the comments of pundits, you'll sometimes note a tone of repulsion when it comes to the big chain.

I haven't been a fan of the shopping experience at Sears either, and it's been a very, very long time since I've stepped into a Kmart. In fact, there isn't a Kmart close to me. Eddie Lampert's enormous task of helping to turn this ship around is not one I envy. Of course, many retailers make the mistake of only focusing on merchandising in the stores and figuring out what should be in the weekly circulars. Don't get me wrong, that's important stuff. But Sears needs to engage a branding campaign to make people feel good about its stores, to feel confident about the shopping environment. When you look at TV ads by Wal-Mart (NYSE: WMT) and Target (NYSE: TGT), you can't help but marvel at the branding acumen of those retailers. Sears needs to get creative, too.

As we begin the trek to grandmother's house, it's worth reflecting on what we have to be thankful for. The answer? When it comes to money, most of us have a lot less than we did a year ago. But for those of you who have your health and your families to comfort you, it will cost much less to buy the gasoline to visit than it would have in July. And as you're driving to visit those families -- consider how much less you lost in the last year than the world's 10 biggest losers.

According to the web site, The Business Sheet, those unfortunate people suffered a mind-boggling $176 billion in lost stock market value in the last 12 months. It turns out that 52% of the losses were suffered by three executives based in India. Here they are:

• Anil Ambani - $32.5 billion. Ambani heads Reliance Communications that invested $500 million in Dreamworks earlier this year.
• Lakshmi Mittal - $30.5 billion. Mittal heads ArcelorMittal which has suffered from a decline in the price of steel.
• Mukesh Ambani -$28.2 billion is Anil's brother and controls Reliance Industries, a petrochemical manufacturer.

These are some other folks that make The Business Sheet's list:

• Sheldon Adelson -$30 billion. I did consulting work for Adelson about 22 years ago and he is quite a character. His Las Vegas Sands (NYSE: LVS) casino is suffering from the economic slowdown and he's had some trouble with debt.
• Warren Buffett -$13.6 billion. As I posted, Buffett's Berkshire Hathaway (NYSE: BRK.A) has had some problems this year.

Just as soon as Sears Holdings (NYSE: SHLD) re-arranged deck chairs on the Titanic, the retailer, headed by hedge-fund guru Eddie Lampert, reported another absolutely dismal quarter Thursday morning. In 2008, shares in Sears Holdings have sunk 36% as the retailer continued to report quarter after quarter of sluggish sales, declining revenue and underinvestment in its retail locations.

Lampert's idea of cutting investment in stores to boost actual investment returns has failed, and failed miserably. One thing customers respond to is constant change in their shopping environment, and this is where Sears has failed. Its stores look the exact same as they did four years ago. Even the logo has not changed.

Retailers like Target Corp. (NYSE: TGT) and Wal-Mart Stores, Inc. (NYSE: WMT) apparently know way better how to get seasonal and high-request goods to their stores. They do it in a fashion that turns inventory and makes sales far better than Sears' manages with its current grip on retail. In fact, I am not sure Sears even has a current grip of retail. It's a goldfish (albeit a large one) nearing the top of the fishbowl. With Lampert's track record, one would think he would have made changes a year ago. He has not, and Sears continues to flounder badly. The Wall Street Journal thinks Lampert should go, and go now. What do you think?

Even Lampert's acumen in taking out pieces of an investment and selling for a profit hasn't worked out. What about selling off a good portion of its real estate holdings under the combined Sears/KMart umbrella to help make a profit? Even that time has passed though. Lampert's original prediction for Sears Holdings has failed, and unfortunately he won't be adding this experiment to his resume that includes the years-ago notion that he was the next Warren Buffett.

This past week, Sears Holdings Corp. (NASDAQ: SHLD) announced the addition of two new senior executives to replace the departing heads of its business segments. The former head of Motorola's (NYSE: MOT) mobile devices business, Stu Reed, will become senior vice president of Sears's home services unit. His predecessor was Mark Good. Former Procter & Gamble (NYSE: PG) senior executive Guenther Trieb will take charge of the Kenmore, Craftsman, and Diehard brands.

Hoffman Estates, Ill.-based Sears also announced the impending departure of Chief Marketing Officer Maureen McGuire. Senior vice president Richard Gerstein, also of the marketing team, will serve as chief marketing officer of Kmart and Sears.

Earlier this year Chairman Eddie Lampert split the company into five business units. But, the company reported in May its largest quarterly loss since the merger of Kmart and Sears in 2005. The company is scheduled to report second quarter results this week. Analysts surveyed by Thomson Financial on average expect a profit of 33 cents per share, up from a loss of 53 cents in the previous quarter, but still down from net income of $1.14 in the same quarter a year ago. Also, Sears has tended to offer negative surprises in the most recent quarterly reports. Analysts rate Sears as underperforming.

Shares closed Friday at $88.43, which is down 13.4% since the beginning of the year and down 38.4% from a year ago.

KB Home (NYSE: KBH) shares are trading higher after a report that hedge fund manager Edward Lampert has bought "small stakes" in homebuilders Centex (NYSE: CTX) and KBH, thinking that the housing market may be poised for a recovery. Investors are taking this news as a good sign for KBH. If you think that the stock won't fall by too much in the coming months, then now could be a good time to look at a bullish hedged trade on KBH.

After hitting a one-year high of $44.51 last June, the stock hit a one-year low of $15.76 in January. KBH opened this morning at $18.21. So far today the stock has hit a low of $18.15 and a high of $19.07. As of 12:00, KBH is trading at $18.87, up 1.00 (5.6%). The chart for KBH looks bearish and steady, while S&P gives the stock a negative 2 STARS (out of 5) sell rating.

For a bullish hedged play on this stock, I would consider a July bull-put credit spread below the $15 range. A bull-put credit spread is an options position that combines the purchase and sale of put options to hedge risk in case the stock doesn't do what you think but still leverage nice returns. For this particular trade, we will make an 11.1% return in just five weeks as long as KBH is above $15 at July expiration. KBH would have to fall by more than 20% before we would start to lose money. Learn more about this type of trade here.

KBH hasn't been below $15 at all in the past year and has shown support around $17.50 recently. This trade could be risky if the financial sector continues to tumble or if the Fed makes its first interest rate hike in a while, but even if that happens, this position could be protected by the support the stock might find around $16 where it put in a bottom in January.

Brent Archer is an options analyst and writer at Investors Observer.

DISCLOSURE: Mr. Archer owns and/or controls diversified portfolios of long and short stock and option positions that may include holdings in companies he writes about. At publication time, Brent neither owns nor controls positions in KBH.

Sears Holdings (NASDAQ: SHLD) really blew its earnings numbers. According to Briefing.com, Sears' Q1 adjusted earnings missed by 68 cents. Nope, no beating by the proverbial penny here, folks. Sears was expected to report an adjusted profit closer to 15 cents per share; instead, not the 53 cent loss booked by the retailer. Man, that's bad. Wall Street also expected a better top-line performance. But Sears couldn't come through on that count, either. Net sales for the quarter declined almost 6% to a little more than $11 billion.

But wait, there's more bad news. Same-store sales at Sears took a turn for the worse, diving almost 10%! Comps at Kmart decreased 7%! The gross margin went down! Want more, or is that enough? The Sears story is not a good one. What's going on here? Well, the release does say something about a bad economy, but that isn't a worthwhile excuse. Sears simply needs to apply itself and get traffic into its stores. Use some thinking-outside-of-the-box marketing campaigns to reignite the brand's fire.

Today's stock market rally may be more of a relief run than anything, but the end of day strength of late has been hard to ignore. Today we saw a huge drop of almost 9 million barrels of oil that caught traders off guard, but interestingly enough the oil markets dropped considerably. Combine that with a slightly higher revision to Q1 US GDP to +0.9% and all of a sudden the recession isn't looking so serious. These are the major US index closing levels:

• DJIA 12,642.47 (+48.20)
• S&P500 1,398.03 (+7.19)
• NASDAQ 2,508.32 (+21.62)
• 52-WEEK LOWS
• Top 10 Analyst Calls (ALU, CHS, LONG, IFX, JNPR, MAR, MFA, NSC, SNDA, VVUS)

Big Lots Inc. (NYSE: BIG) beat earnings and raised certain parts of guidance, and shares were up over 9% at $31.21 in the final minutes of trading.

When Edd Lampert merged K-Mart and Sears Roebuck into Sears Holdings Corp. (NASDAQ: SHLD), he probably didn't plan for a complete and unmitigated disaster. But, from all accounts, that is what the company is at this time. Its sales have consistently plummeted for more than just a few quarters now, the competition has killed it. Sears merchandising frankly is really, really bad -- and on and on.

Lampert's grand vision is still alive, but the realities of running a national retailer in an intense environment have not proved easy at all. What's keeping Sears Holding's shares above $100, you say? Check out the company's vast real estate holdings. Don't think for a second that this isn't the reason Sears is majority owned by Lampert, who could care less about the retail end of the business.

Still, you have to run a business. It's always nice to see that a former CEO who appeared to do virtually nothing in terms of performance get an annual base salary of $1 million through the next few years -- even though he's no longer at the company. Ousted CEO Alwyn Lewis, who was highly regarded when recruited for the Sears Holdings CEO spot but who was wholly ineffective, will receive his salary package through March 24 of 2010. Lewis will also continue to have health and welfare plan availability along with having his remaining stock and option awards vest until 2010 as well.

Even though the boards of public companies should be completely separate from the management and owners of the company, it's hard to see that they're not when excessive, after-term packages like this come to light. Pay for performance? Hogwash. CEO compensation committees can be as corrupt on company boards as those Enron folks from years back. Well, to a degree, anyway.

Super-investor Eddie Lampert has cut his stake in Citigroup Inc. (NYSE: C) by 31%, leaving him with a position of 19.1 million shares valued at a little under $500 million. It is likely that Mr. Lampert sold the shares at a substantial loss.

Lampert's large presence in the stock was a source of confidence for battered bulls who watched the stock decline through subprime write-downs and a managerial shake-up. Long considered to be one of the great value investors, Lampert's latest 13-F filed with the SEC shows stakes in Acxiom Corp. (NASDAQ: ACXM), AutoNation Inc. (NYSE: AN), AutoZone Inc. (NYSE: AZO), Citigroup, Home Depot Inc. (NYSE: HD), and, of course, Sears Holdings Corp. (NYSE: SHLD).

Lampert's decision to cut his stake in Citi has to make investors nervous. He's ridden the stock down for months, and it hasn't exactly been rebounding.

Last year was tough for Lampert, with Sears' stalled turnaround bringing him poor returns and the worst publicity of his career.

Eddie Lambert may have to loan Sears Holdings (NYSE: SHLD) some money. Cash at the company be getting very tight. According to the Wall Street Journal, "some analysts wonder whether falling sales, slimmer profit margins and other woes are causing cash flows to decline to a level that could hinder a turnaround."

The last cash balance that Sears announced was lower than most analysts expected. If the company needs to spend money to improve its stores or increase inventory in products it thinks will sell well, it could draw down the cash level even further.

For Lampert, the bad news keeps getting worse. Sears stock has staged a mini-rally over the last two weeks, moving from below $85 to $103. News about cash problems could push the shares back down.

Lampert made the classic error of thinking that with Sears and K-Mart 1+1=3. In reality, he took two weak companies and saved some money in a merger. The problem was that the companies got even weaker.

Who says that hedge fund managers don't make good corporate chiefs?

Douglas A. McIntyre is an editor at 247wallst.com.