There are so many shoes falling around Sears Holdings (NASDAQ:SHLDQ) that an investor risks getting squashed like a bug.

Investors are about to get steamrolled by the string of misfortune striking the retailer. Photo: Flickr user Mike Mozart

Earlier this week the New York Post reported the troubled retailer failed to find a bidder willing to pay enough to buy its equally desperate Canadian operations, and now the CEO of the northern unit announced he will resign his position no later than Jan. 1 -- using the catchall phrase "for personal reasons." Worse, rumors are swirling that Sears Canada is about to go bust.

Chairman Eddie Lampert was forced to infuse the parent organization with $400 million in short-term loans last week to get it through the Christmas selling season. As the company continues to burn through cash at an alarming rate, the latest string of developments may just hasten its demise.

Some of Sears' biggest, best assets were its various brand name divisions. Through either sales or spinoffs, Lampert has methodically stripped them away as a means to artificially prop up Sears with cash.

From Sears Hometown & Outlet Stores (NASDAQ:SHOS) and Orchard Supply to Land's End (NASDAQ:LE) and now Sears Canada, Lampert has been slowly liquidating his company.

He was once hailed as a Warren Buffett wannabe, with Wall Street buying into the storyline that taking two failing businesses and mashing them into a whole could create another Berkshire Hathaway vehicle for building an empire.

Besides, as bullish investors were quick to point out, there was a huge store of value built up in Sears real estate that could be tapped into if needed.

As has become all too plain though, that's not worked out as planned. Instead investors have been treated to a long list of one-time infusions that leave it scrambling each quarter to find the next bit of scrap with which it can use.

This quarter it was apparently going to be Sears Canada.

Revenues at the retailer tumbled 16%, or by $140 million in the second quarter, driven by a 6.8% decline in comparable store sales, which accounted for a third of the revenue shortfall, even more than closing down stores.

Last year, after selling a number of high-profile leases at urban malls back to their landlords -- raising cash using Lampert's signature one-time only formula -- and Sears Canada paid its investors (including Lampert) a $509 million special dividend. The year before it paid a $102 million special dividend.

Yet despite a protracted downturn in fortunes that saw revenues fall to $3.9 billion in 2013 as competition from rivals like Target (NYSE:TGT) and Wal-Mart (NYSE:WMT) entered the Great White North and established players such as Hudson's Bay recovered, Sears Canada miraculously increased in value.

In its latest quarterly SEC report Sears said its 51% interest in the Canadian business had a market value of approximately $765 million in mid-August, up from $730 million in May and a $145 million more than the $620 million it pegged it at at the end of last year. Maybe there is some magic at play here.

We may be seeing a lot more of this soon. Photo: Flickr user Nicholas Eckhart

But not even its CEO seems to think it can continue pulling rabbits out of the hat. Douglas Campbell, who has been in the top spot at Sears Canada for just a year, will be resigning by the time New Year's rolls around.

And the New York Post also said it may be considering filing for bankruptcy. While the company flat out denies the rumor, the paper said a bankruptcy law firm in Canada had been contacted about being retained.

Adding to the confusion, Lampert's loan to Sears Holding from last week is in danger of unraveling. The New York Times this time reports real estate firm St. Joe Company declined to participate in financing Lampert's loan to the retailer. One of Sears biggest investors Fairholme Capital Management, which has a 23% in the company, is now scrambling to arrange other backers.

The decline of Sears Holdings has been a slow-motion train wreck stretched across years. Its stock has dropped 28% since it announced the $400 million cash injection last week and it has lost nearly two-thirds of its value since its 52-week high last November.

The hits are piling up in rapid succession however, and it doesn't seem long before Sears Holdings itself may be stamped out.

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.