In President Trump's youth, Sears dominated American retailing, with department stores scattered across the country and a mammoth catalog business that was the Amazon of its generation.

That made the Hoffman Estates, Ill.-based company's bankruptcy filing early Monday all the more poignant, Trump told reporters before leaving the White House to inspect damage in Florida from Hurricane Michael.

"To somebody that is of my generation, Sears Roebuck was a very big deal; it's very sad to see," the president observed. "Sears has been dying for many years. It's been obviously improperly run, and it's a real shame."

The retailer, which has obtained commitments for $300 million in debtor-in-possession financing, will close 142 of its 866 Kmart and Sears stores before year's end while attempting to reorganize around a smaller core of profitable sites, according to a statement. The company listed assets of $6.94 billion in its petition for Chapter 11 bankruptcy protection in federal court in Manhattan, compared with total debt of $11.3 billion.

Along with the filing, Eddie Lampert, whose ESL Investments is Sears' largest stockholder and creditor, stepped down as chief executive officer but will remain chairman of the board. Directors created an Office of the CEO to manage day-to-day operations; it will include Chief Financial Officer Robert Riecker; Chief Digital Officer Leena Munjal, and Apparel and Footwear President Gregory Ladley.

[Previous coverage: Sears' biggest stockholder pushes for breakup]

"Over the last several years, we have worked hard to transform our business and unlock the value of our assets," Lampert said in the statement. "While we have made progress, the plan has yet to deliver the results we have desired."

Sears posted a loss of $1.31 billion in the 12 months through January, according to regulatory filings. The company, which hasn't posted a full-year profit since 2011, traces its roots to the late 1880s, when railway station agent Richard Sears began selling lumber and coal in his spare time to earn extra cash, according to a history of the company posted on its website.

He eventually moved from Minnesota to Chicago and partnered with Alvah Roebuck to form Sears, Roebuck & Co., a mail-order business that offered lower prices to farmers than the stores in their neighborhoods by taking advantage of large-volume inventory purchases, railroads, and the Postal Service.

By the time the U.S. entered World War II in 1941, Sears was operating 600 retail stores. The new headquarters it opened in downtown Chicago in 1973, Sears Tower, was the tallest building in the world at 1,454 feet, surpassing both New York City's Empire State Building and the twin towers of the World Trade Center.

Over its 130-year history, Sears also created a variety of products and companies that have become household names. Allstate Insurance was formed as a subsidiary providing low-cost auto coverage in the 1930s, and credit-card company Discover began with the retailer's attempt to offer an alternative to MasterCard and Visa in 1985.