Sears stock has fallen into the bargain bin.

In the latest indignity for a once-grand retailer, the share price fell below $1 on Friday for the first time in the company's history, dropping as much as 15% to 85 cents in midday trading.

Falling into loose-change territory is more than embarrassing. Nasdaq, the exchange where Sears stock trades, could delist the company. That's a long process and would happen next year at the earliest.

Shares of Sears Holdings (SHLD) had already plunged 88% in the past year. They took another blow Monday, when CEO and primary shareholder Eddie Lampert warned the board that the company was running out of time and cash. He said Sears must restructure and cut its debt "without delay."

Lampert pointed to a $134 million debt payment due on October 15, and said the company must demonstrate to lenders by Monday that it has required levels of cash in reserve, which could itself prove difficult.

Sears' market value has fallen to less than $100 million. Lampert recently offered to buy the Kenmore appliance line through his hedge fund for $400 million, suggesting that the Kenmore brand on its own is worth more than four times as much as the whole company.

All of which is a stunning reversal for a company that was once not only the nation's largest retailer, but also its largest employer.

In its heyday, Sears was both the Walmart (WMT) and Amazon (AMZN) of its time. In the late 19th century and early decades of the 20th century, many Americans bought mass-produced goods for the first time through the Sears catalog. Most lived on farms and in small towns, and had previously made many of the goods they needed, such as clothes and furniture, themselves.

Sears stores helped reshape America itself, drawing shoppers away from traditional Main Street merchants and into malls, contributing to the suburbanization of the country after World War II. And its appliances introduced many American homes to labor-saving devices that changed family dynamics.

But long before the rise of Amazon and online shopping, Sears struggled to keep up with changing shopping habits.

Big box retailers such as Walmart beat it on both price and selection. In 1999, Sears was booted out of the Dow Jones industrial average, where it had been for 75 years. Home Depot (HD) took its place.

In more recent years, Sears has struggled just to stay alive.

It told investors last year that there was "substantial doubt" it could stay in business. Lampert's latest warning to the board raised a similar warning. He said it was in the best interest of creditors and shareholders to restructure the company "as a going concern."

Sears has lost $11.7 billion since 2010, its last profitable year, and sales have plunged 60% in that time. It has fewer than 900 stores, down from a combined 3,500 US stores when Sears and Kmart merged in 2005.

In July, the company closed the last Sears store in Chicago, its former hometown. And the company recently announced that 46 more stores will close just before the holiday shopping season.