Per CNBC - After years of Sears Holdings staying afloat through financial maneuvering and relying on billions of CEO Eddie Lampert's own money, the 125-year-old retailer filed for bankruptcy.

The filing comes more than a decade after Lampert merged Sears and Kmart, hoping that forging together the two struggling discounters would create a more formidable competitor.

It comes after Lampert shed assets and spun out real estate, all to pay down the debt the retailer accumulated when that plan went askew. The company still has roughly 700 stores, which have at times been barren, unstocked by vendors who have lost their trust. Many of the stores have never been visited by a generation of shoppers that can barely recall it was once the the country's biggest retailer.

Lampert, who has a controlling ownership stake in Sears, personally holds some 31 percent of the retailer's shares outstanding, according to FactSet. His hedge fund ESL Investments owns about 19 percent.

Ultimately, it was a $134 million payment that did the company in. The company had a payment due Monday it had not the money to pay.

Other forces were at play too. Sears' creditors refused to agree to a restructuring proposal. They had little assurance by way of collateral or strategy, after years upon years in which Sears' only shot at survival came by selling off parts of its business. Over 42 quarters, only one yielded positive same-store sales growth. As of late September, Sears tallied $5.6 billion in current debt.

Its board was in a perilous spot. Its special committee was tasked with approving Lampert's other plan, a bid to buy his storied Kenmore appliance business and other brands. Approving his offer would have helped Sears make its payment. But it would also thrust the board the spotlight, potentially opening them to the threat of litigation from shareholders who might allege Lampert has stripped the business bare.

Homes to Hardware

That business was once a giant. It started with Richard Sears, who launched the Sears Watch Co. in 1886 to sell watches by mail. The company later evolved into Sears, Roebuck and Co., which sold everything from homes to hardware through a catalog. The convenience brought its products to America's most rural locations.

In 1925, Sears morphed a mail-order plant on Chicago's West Side into its first retail store. By the end of the year. Sears opened seven more stores. Eventually, Sears became the largest U.S. retailer, and its house brands like Kenmore and Craftsman earned spots as staples in homes across the country. Generations of children marked the holidays by paging through its holiday catalog, known as the "Wishbook," wondering if they would receive any of the toys inside.

As Sears success grew, so did its empire. It moved into Chicago's iconic Sears Tower, and for a time, owned financial services businesses like Dean Witter and Coldwell Banker Real Estate Group.

But Walmart topped Sears as the biggest U.S. retailer in 1990. Its efforts to attract female shoppers by showing them the "softer side of Sears" and move into new businesses lines left it without a identity.

Those challenges didn't stop Lampert, the hedge fund manager who had already impressed Wall Street with his acumen when he seemingly turned around Kmart, which he bought in 2004. He acquired and combined Sears with Kmart in 2005, arguing that two ailing retailers were stronger together than apart. The financial guru saw valuable real estate, customers he could parlay from one store to the other and ample costs to cut.

The retail giant he created had a market capitalization north of $20 billion in 2006. The media began to wonder whether he was the "next Warren Buffett." Lampert could have sold off his investments then, but stayed on, steadfast in his vision of the combined retailers.

Meanwhile, Walmart and Target kept opening stores, as did Lowe'sand Home Depot. Walmart touted its "everyday low prices," while Target served up "cheap chic." Lowe's and Home Depot provided a wider array of home improvement products for all kinds of projects, making it tough for Kenmore and Craftsman to compete.

Then, came a double blow.

Consumer spending slowed during the Great Recession, especially for big-ticket items like washers and dryers. Cash-strapped shoppers began using the internet to hunt down the best deals. Gradually, they began to spend more online and avoid the mall, fueling Amazon's rise. Sears' 140,000-square-foot stores began to seem monstrous as foot traffic declined.

Walmart and others began to invest in their businesses to compete with Amazon, but Sears never had that chance. It simply didn't have the funds.

Sears' last profitable year was in 2010. A thinning cash flow has left little money to put back into the company itself, letting it become more irrelevant. For the past five years, the ratio of Sears' capital expenditures to sales has been less than one percent. That's even as its sales have more than halved in the same time period.

Sears has been in survival mode for more than a decade. Unable to rely on the Sears' business to pay the bills, Lampert instead sold or spun off many of its most valuable stores and brands.

Since its merger with Kmart, Sears has spun off its Lands' End clothing brand, sold the Craftsman tool brand to Stanley Black & Decker and closed hundreds of stores. It spun out 250 of its best properties into real estate investment trust offshoot known as Seritage.

Its key vendors, wary of Sears' future, demanded tighter payment terms. Some, like Whirlpool, stopped shipping all-together.

It has been grappling with a pension of roughly 100,000 retirees that, as of January 2018, was underfunded by $1.5 billion, according FactSet.

It became a guessing game among analysts and onlookers whether each of Sears' last five holiday seasons would be its last. But Lampert kept surprising them, extending a lifeline in the form of loans from his hedge fund ESL Investments, or finding them elsewhere, each time bankruptcy looked inevitable.

Lampert, though, sounded the alarm in a Sept. 13 blog post. He pleaded for Sears' creditor's to agree to restructure, calling out the risks should they drag their feet.

"We continue to believe that it is in the best interests of all our stakeholders to accomplish this as a going concern, rather than alternatives that could result in significant reductions in value," he wrote.

By early October, it became evident that Sears' last Christmas before bankruptcy had already passed. Sears began to raise emergency financing to support the business through coming filing.

Now, the question will be whether Sears will be able to come out of bankruptcy. Retailers don't have a great track record of emerging. Several of late, like Toys R Us and department store Bon-Ton, have been forced to liquidate. It is difficult to make changes needed, like investing in e-commerce, stores and a company's brand, while still catering to creditors' demands.